Lower Florida Keys Vacation Rentals, Homes & Cottages
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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Lower Florida Keys, Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals in Lower Florida Keys to choose from, we now have the selection and value to offer our visitors going to Florida.
Villa of the Setting Sun - Sugarloaf Key House
Luxurious Oceanfront Home w/ a Private Pool, High-Speed WiFi, & Private Beach
Villa of the Setting Sun Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Recline with a beverage on your own private beach, or take a dip in the private heated pool with a view. You've just arrived at this beautiful home by the sea, surrounded by leafy trees and beautiful water. Inside, you'll relax in central air conditioning in a luxuriously decorated spa.......read more
4 Bedroom(s)
5 Bath(s) - Sleeps 8 House Rentals
Pelico Palms - Sugarloaf Key House
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers
Pelico Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' This unique, Southern-style home features plenty of space for everyone in your group—plus a private, heated outdoor pool where everyone can come together! The Tiki hut, with its outdoor bar, waterfall feature, and comfortable poolside seating, and the screened-in game room, complete with Ping-Po.......read more
10 Bedroom(s)
7 Bath(s) - Sleeps 20 House Rentals
Palms Resort at Sugarloaf - SUGARLOAF KEY House
One of a kind beach house with a private sandy beach, dock and boat dockage . A modern tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Clear blue Florida Keys waters, great for swimming, snorkeling, kayaking, paddle boarding or just relaxing. With its privileged location and its close proximity to one of the worlds top vacation destinations, Key West, our beach house will allow yo.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Sugarloaf Shores - Sugarloaf Key House
Spectacular Open Water Hawaiian Style Home for the Savvy Traveler
Stunning open water views at this drop dead gorgeous Sugarloaf Shores home. Hawaiian style architecture boasts wrap around balconies with 2 separate stairs that encompass the entire home. Large downstairs entertaining and seating area with summer kitchen, table for 8, full bathroom with shower, outdoor shower, tiki hut with 4 chairs, and beach area all on Sugarloaf Sound. Beautifully landscaped yard with boat lift, kayak, and pathways that mean.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Sunrise Point at Sugarloaf - Sugarloaf Key House
Waterfront Home w/ WiFi, Private Washer/Dryer, Firepit and Private Gas Grill
Sunrise Point at Sugarloaf Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Unwind in paradise with a tropical drink melting in your hand, either on a private balcony or around the firepit while the stars come out. This home's upscale beach house decor sets the tone for a tranquil vacation near the water. Multiple comfortable spaces lie indoors and out, so e.......read more
4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals
VeryClean Canal Front Home 3/2 - Cudjoe Key House
Canal Front, Spa/Pool, 2 Kayaks, 2 Bikes, 3 Bed, 2 Bath, Oceanside Home
Heated 8' x 14' above ground Spa/Pool! Free 2 two-man Kayaks during your rental, plus 2 bikes! Wonderful elevated home across the street from open water. Home sits on a sea walled canal with room for boats and offers a secluded porch overlooking the canal. This is a very CLEAN, three-bedroom/two-bath home. Turn-key property with all items available for your use from towels to bedding, to pots and pans, just bring your bathing suit, toothbrush.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 5 House Rentals
Vacation Rentals - Cudjoe Key House
BEAUTIFUL MODERN NEWLY RENOVATED 3/3 HOME W/ DOCK, TOYS,2 KITCHENS NEAR KEY WEST
Modern, newly renovated, 3/3 with 2 full kitchens on canal with ocean access and ocean views. LARGE 2 STORY HOUSE ONLY 21 MILES FROM KEY WEST AIRPORT AND 6 MILES FROM BAHIA HONDA. HOUSE IS SPACIOUS AND GREAT FOR LARGE FAMILIES. YARD IS SECURED WITH PLENTY OF SPACE FOR TRAILER AND ALL YOUR WATER TOYS. DOCK EVEN HAS OPTIONAL “POOL FENCE” FOR CHILD/PET SAFETY. 60’ DOCK WITH NO BRIDGES TO OCEAN. 1st floor has 1 bedroom, 1 bathroom with full k.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Blue Chill Vacation!!! - Cudjoe Key House
Bright, colorful and tropical this freshly remodeled home is located within easy walking distance to convenience store and swimming pool /spa and ocean swimming are! You are close to everything!! Cook inside in easy access kitchen with large counter space. This unit is not on the canal, but you can bring your boat ! Boats can be stored in the 'overflow' lot for a small fee paid directly to the park office. The boat ramp is on site along with fu.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
Seascape Vacation!!! - Cudjoe Key House
Beautiful vacation spot on Cudjoe Key perfect for you and your family. This wonderful one bedroom home filled with colorful patterns can turn a boring vacation to an adventurous one. If you stay here you’ll definitely have the perfect tropical vacation in paradise. VO REGISTRATION FEE $107.50 DUE UPON ARRIVAL. Enjoy community activities and full use of the amenities; Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, P.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
"Seas The Day" in Cudjoe Key - Cudjoe Key House
A cozy and small mobile home with Marina access and a boat ramp. With almost perfect weather you experience in the Keys you're bound to tan on the back half of this property. With a shared gym and tennis court there's never a dull moment on this Marina. Experiencing an almost perfect mix of a more rustic yet still modern aesthetic you are most definitely going to feel at home while staying here. Staying here you'll most definitely have a fu.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
Paradise Found - Cudjoe Key House
3 bedroom accommodation in Cudjoe Key
Newly built canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stainless appliances, plank flooring, beautiful tray ceiling over the living area and large windows. French doors out to the covered porch with seating overlooking the canal. Super-comfortable reclining sectional with 55-inch TV in the living room. Satellite TV and high-speed satellite Internet and WiFi. Master suite has.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Catch n' Relax in The Keys! - Cudjoe Key House
Amazing waterfront property. VO REGISTRATION FEE $107.50 DUE UPON ARRIVAL. Enjoy community activities and full use of the amenities; Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fish Cleaning Station, Horseshoes, Ping Pong, Children's Play Area, Bocce Ball, 24 Hour Gated Security, Salt Water Swimming Area, Recreation Hall and Pickle Ball Co.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
El Paraiso - Cudjoe Key House
2 bedroom accommodation in Cudjoe Key
Adorable 2 bed/2 bath canalfront home with great outdoor living space and boating access to the Atlantic Ocean. Master bedroom has a queen and a full bed and the second bedroom has two full beds. Newly remodeled bathrooms. Fully equipped kitchen. Plenty of seating and lounging opportunities in the canalfront backyard. Small downstairs storage for your gear. Off-street parking with room for your trailer. Walking distance to the popular Square Grou.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Calico Jack Hideway - Cudjoe Key House
Relax and enjoy this 3 bedroom/2 bath home on the oceanside of Cudjoe Key that offers the best of Keys living with excellent boating. Open concept living area provides all the comforts of home. This is a well-maintained home with newer furnishings. Plenty of seating in the living room, with dining tables inside and out. 3 queen beds, lots of storage space and 2 full baths w/laundry. Basic channel DirectTV and AT&T broadband/WiFi. The expansive co.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Cozy, Perfect Conch Cottage! - Cudjoe Key House
Everything what you need for perfect vacation you will find in the cozy walls of Conch Cottage. Open great room, washer and dryer in unit, fully equipped kitchen, comfortable living room, outside covered porch with patio furniture.v Enjoy community activities and full use of the amenities; Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fis.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
EMPTY RV LOT - Latitude Adjustment - Cudjoe Key Mobile home
EMPTY RV LOT - Latitude Adjustment
THIS RV LOT has it all! Just stop by and hook up your RV or boat, then head to one of many community amenities like basketball courts and tennis courts! While pet friendly, hot tub or pool awaits you at the end of each day's activities in this beautiful area. NO RENTAL RV'S ALLOWED TO STAY THERE. VO REGISTRATION FEE DUE UPON ARRIVAL........read more
1 Bedroom(s)
1 Bath(s) - Sleeps 1 Mobile home Rentals
EMPTY RV LOT - Sea Esta in Cudjoe Key! - Cudjoe Key Mobile home
EMPTY RV LOT - Sea Esta in Cudjoe Key!
This RV LOT has it all! This is a great spot for those who want to enjoy open water views without having the hassle of getting there. There are plenty of open water views, boat dock for your convenience. Just stop by and hook up your RV or boat, then head over to one of many community amenities like basketball courts and tennis courts! While pet friendly, hot tub or pool awaits you at the end of each day's activities in this beautiful area that .......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 6 Mobile home Rentals
Vacation Rentals - cudjoe key House
Looking for a great getaway that is convenient, close to everything and affordable? Cudjoe Escape is just for you. This three bedroom two bath canal front home offers a comfortable base for your Keys adventures. The living room, dining room, and kitchen are all found in an open area adjacent to the screened porch. There is also an open porch off the kitchen. The kitchen is updated with granite counters, fully equipped and ready. The furniture is .......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals
Vacation Rentals - Cudjoe Key House
Cozy and modern island living, Cudjoe Key
Unit #617 Bright, modern, 2bed, 2bath, midrise home. Across from canal and common area. Open floor plan, hardwood, central a/c with fans in every room. Cable TV, wifi, smart TV with Netflix, YouTube, and much more. Full kitchen, dishwasher, microwave, full range top, stacked washer/ dryer. Queen bed in master bedroom with full bath. 2 twin beds in second bedroom. A pullout sofa offering a queen bed. 2 kayaks, 1 SUP board, 4 bikes, outd.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
The Stealth Bomber - Cudjoe Key House
A 2 bedroom 2 full bath (sleeps 6) home that sits on a canal leading to the Atlantic with its own boat basin and dock. Enjoy grilling out while your family fishes and has access to a bike trail across the way. The property is surrounded by landscaping making it private. A boat launch and marina is within walking distance and has boat rentals available. Many great restaurants and drinking establishments are close by, but if you're needing the D.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Vacation Rentals - Big Pine Key House
Mickey and Lynn's House of Windows
Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the property on this lovely sanctuary. Over a hundred feet of dock space and cleaning table. Secluded but convenient, located close to variety of grocery stores, marinas and only 31 miles to Key West. Bedrooms: 3 Bathrooms: 3 Sleeps: 8 This house has in it a lovely that helps you forget .......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Ships Way - Big Pine Key House
3 bedroom accommodation in Big Pine Key
This adorable cottage on the bayside of Big Pine Key is the perfect spot for your Florida Keys getaway, close to shopping, the Overseas Heritage Trail and the wonderful flora and fauna of the National Key Deer Refuge. Trailer your boat to one of the nearby boat ramps. The famous Bahia Honda State Park is just a few miles way. The primary bedroom has a king bed, en-suite bathroom, 50-inch flat-screen TV, tons of storage space, and a bonus space.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 5 House Rentals
Cedar Cottage - Big Pine Key House
2 bedroom accommodation in Big Pine Key
This newly remodeled 2 bed/2 bath home in Big Pine Key's Eden Pines neighborhood is the ideal place for your laidback Florida Keys vacation! Nestled in the quiet Key Deer Refuge on Big Pine Key, this home features a gorgeous, well-equipped kitchen with brand-new stainless appliances and tons of storage. Charming decor with warm wood floors. Brand-new bathrooms, including a huge shower in the master. Walk-around deck and large screened back porch,.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Serenity on San Remo - Big Pine Key House
There's a pool coming for July! Ask for the pool construction discount if booking May or June! Enjoy unmatched privacy and serenity during your stay at this gorgeous canalfront 3 bedroom/3 bathroom home nestled near the end of Doctors Arm on Big Pine Key. There are clear 40-foot-wide flow-through canals on two sides of this lushly landscaped 20,000-square-foot property that sits on the edge of the Great White Heron National Wildlife Refuge. N.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals
Tarpon Tales - Big Pine Key House
2 bedroom accommodation in Big Pine Key
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the channel. Lots of relaxing outdoor living space. Fully fenced and very private. Close to the community park. Fully outfitted kitchen. Each bedroom has a king bed, and there's a queen sofa bed in the living room. Plenty of dockage. Excellent fishing retreat, just minutes from the channel. Well-behaved dog considered with manager's a.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Vacation Rentals - Big Pine Key House
Beautiful clean and spacious home. Relax on your deck or take your boat out, canal goes out to the gulf or ocean to do some fishing or just water sports activities. Deer life all around. Mile marker 38 on Deer Key habitat and wildlife around. Great fishing, and enjoy all festivals with the locals. Great restaurants just a few minutes away. Key West is just a 35 min. drive, Bahia Honda 15 min. The best of paradise........read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Big Pine Latitude Adjustment - Big Pine Key House
Location location location! Room for the whole family in this gorgeous 5 bedroom 3 bath pool home on Big Pine Key. Home is basically all brand new, 100% remodeled floor to ceiling. Sleeps 10. Lounge out at the deep water pool which stays cool in the summer & heater is available for an additional $400/month charge in the winter. Over 200’ of concrete dockage space with quick access to Pine Channel with a 4’ draft – bring the big boat!.......read more
5 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals
Manatee Watch - Big Pine Key House
4 bedroom accommodation in Big Pine Key
Like-new four-bedroom, three-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key. There's a new concrete dock for your big boat and convenient steps into the water for swimming or paddle sports. There are 2 queen bedrooms and 2 full bathrooms on the main living floor and 2 huge queen bedrooms with a shared full bath on the top floor. There are two covered porches with peekaboo views of open water. Fully eq.......read more
4 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals
Casa Del Mar 305 5251254 - Big Pine Key House
Welcome to Casa Del Mar 305 5251254
Welcome to "Casa Del Mar" 305 5251254 a brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , 3BR/2BA pool on deck. You can enjoy stunning oceanfront views from almost every room. For boaters ,fishermen and outdoors men feel free to use the 75 foot concrete boat dock with cleats, bumpers, fish cleaning table, bait freezer and tandem kayaks. There i.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 12 House Rentals
Treasure in the Pines - Big Pine Key House
Paradise Found ! Fully updated Waterfront Home- GREAT FISHING
Fully updated 2 Bedroom/2 bath Canal front home in quiet neighborhood located 20 mins from Key West. -Home elevated on cement pillars -King Size Bed in master, Qty-2 twin beds in 2nd bedroom -Fully furnished kitchen -2 full bathrooms includes sink/toilet/tub, plus outside shower -fisherman's dream home Experience nature at it's finest -Blue Hole, Big Pine Key -Ramrod Swimming Hole (Ramrod Key) great swimming & snorkeling -fish from the dock -K.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Bogie Cottage - Big Pine Key House
2 bedroom accommodation in Big Pine Key
Great spot for boaters! Newly remodeled and nicely appointed 2 bedroom/2 bath canalfront home on Big Pine Key. Everything you need for your time in paradise! There's a queen bed in the master and two twins with a king conversion kit in the 2nd bedroom. Good-sized closets. Flat screens in the living room and both bedrooms. The kitchen has everything you need for your stay. Gas grill and outside table downstairs. Concrete dock. Set on a canal right.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Prince's Keys Serenity - Big Pine Key House
Beautifully remodeled, impeccably decorated and spacious ground-level home in the Tropical Bay neighborhood on the north side of Big Pine Key. Situated on a manicured triple lot at the end of a boating canal, it offers the perfect amount of social distance for your Florida Keys winter getaway. This rental is only available November through April. Multi-month renter preferred. Discount offered for 6-month lease. The fully equipped, modern .......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Natural Serenity - Big Pine Key House
2 bedroom accommodation in Big Pine Key
Enjoy uninterrupted natural vistas from this gorgeous home in one of the Lower Keys' best boating neighborhoods, Pine Channel Estates. This stilted canalfront home with ample concrete dockage on a clean, deep canal is just a few houses in from the channel and just 30 miles from Key West. There are no neighbors across the canal, just trees and key deer. This well-maintained and updated home features an open floor plan and a huge screened porch ups.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Escape to Eden - Big Pine Key House
2 bedroom accommodation in Big Pine Key
Be one of the first to enjoy this newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean space that features all the comforts of home. Central air and ceiling fans in every room keep it super comfortable. The brand new, upscale kitchen is perfect for a lazy breakfast or dinner in. The home features 2 bedrooms with 2 queen beds and a queen sleeper in the living room. There is one full ba.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Changes in Latitude - Big Pine Key House
Tropical Getaway in the Florida Keys
Tropical getaway in Big Pine Key located on a canal that leads straight into Bogie Channel. Vaulted ceilings, open floor plan, master bedroom with walk in closet and private bathroom, 2nd bedroom has a double over double bunk bed plus a pull out trundle bed. Spacious hall bath, queen sofa bed in living room, and large screen porch make this a perfect spot for your next vacation. No Name Pub is within walking distance from the house...great s.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals
Reel NV - Big Pine Key House
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in desirable Doctor's Arm neighborhood, this house is just around the corner from the famous No Name Pub on Big Pine Key. Quick idle to Spanish Harbor Channel and easy access to the ocean or the gulf. Less than a mile from the No Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Paradise Retreat ~ BPK - Big Pine Key House
~3/2 home with heated pool located on large ,private and fenced property. Screened room and patio deck. Privacy is key to relaxation here on this property in Big Pine Key. ~Boat ramp within 1/4 mile with excellent access to Gulf~Atlantic ~Quick 20 minutes to our favorite "Square Grouper Restaurant", 45 minutes to Key West and 25 minutes to Marathon and other favorite "Burdines" ~Beautiful Winn Dixie grocery store on BPK ~28 day minimum rental f.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Lobstertail Lair - Big Pine Key House
Big Pine 2/2 ,Water Views and Sunsets Located Oceanside Now rentting 20 seas
Nice Quiet 2 bedroom 2 bath beach cottage located oceanside of US 1 on a swimming canal next to open water canal. Sunset and open water view. Boat slip to open water next door by same owner. New Kitchen and all furnishings 2010. Close to all shopping and activities On Big pine Key and a short drive to Key West without all the crowds. Beautiful sunsets from the outside patio overlooking the bay. In Immaculate condition and recently renovated. New.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Casa Del Mar 305 5251254 - Big Pine Key House
Welcome to Casa Del Mar 305 5251254
Welcome to "Casa Del Mar" (305) 5251254. a 3/2 brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , pool on deck. You can enjoy stunning oceanfront views from almost every room. For boaters ,fishermen and outdoors men feel free to use the 75 foot concrete boat dock with cleats, bumpers, fish cleaning table, bait freezer and tandem kayaks. There is .......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 12 House Rentals
Keys to the Kingdom - Big Pine Key House
Beautiful Home Right on the Water with a Private Beach, WiFi, Private W/D, Deck
Keys to the Kingdom Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' There's no better place to experience the magic of the Florida Keys than this bright and newly-remodeled three-bedroom getaway! Step inside to find a spacious open-concept layout boasting an ocean view, beautiful floors, and comfortable and attractive furniture. After spending an afternoon .......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals
Casa de Sueno - Little Torch Key House
5 bedroom accommodation in Little Torch Key
Completely remodeled 5 bedroom / 2.5 bathroom home with excellent water access on Little Torch Key. Double lot with 120-foot seawall. Large outside sitting and dining area. Gas grill. Plenty of parking. Water access via Pine Channel, one bridge with 17-foot clearance. Fish cleaning station and water and power at dock. Pool with a heater/chiller available for a monthly charge of $400. Walk into the home to a dining table, kitchen to the righ.......read more
5 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals
Vacation Rentals - Little Torch Key Mobile home
Pirates Pleasure Fishing and Snorkeling.
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property has out door kitchen and Pit Boss smoker, large screened porch, large Tiki Hut , also has hot tub. Charters are available for fishing and sun set cruise's. Kayak's and Bicycle's available. Boondocks bar and grill approx 5 miles from property. Like us on FB. Pirates Pleasure.. Call Shane 305 -432-1418.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 6 Mobile home Rentals
Little Torch Hidden Gem - Little Torch Key Mobile home
Little Torch Hidden Gem - a perfect place relaxing and water activities
This home is a great place to get away from the rigors of life and enjoy the peace and quiet of the lower keys or get out and partake in all types of water activities. Little Torch is centrally located in the keys but will make you feel like you are miles away. This is a canal front home, maintained in excellent condition with a new deck all new flooring throughout in summer 2015. The canal is wide enough to dock a 25 foot boat with no proble.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 Mobile home Rentals
Vacation Rentals - Little Torch Key House
This is the perfect Keys paradise home. It is in a friendly neighborhood close to all your needs. After a busy day on the water, relax and gaze at the stars in the comfortable adirondack chairs. Fully equipped home that sleeps 6 (king, queen and twins). Large porch overlooking canal with gas grill faces North for great evening entertaining. Enough room at the dock for a 30 ft. boat (deep water canal) and great fish cleaning station. Garage downst.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
AJ's Hideout - Little Torch Key House
Waterfront snowbird escape with private 40’ boat dock, amazing views & W/D
AJ's Hideout Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Quiet privacy, sweeping water views, and enviable proximity to water activity make this canal-front home a dream retreat. Start vacation days with your morning beverage of choice on the furnished wraparound deck overlooking the Torchwood Hammock Preserve. Swing in the hammock and admire the dreamy.......read more
4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals
Vacation Rentals - Little Torch Key House
2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
Our cozy 2 bedroom 2 bath 2 story home with a private pool offers a vacation to remember in the Lower Keys. Located in Little Torch Key and walking distance to breath taking water views and full access amenities such as bocce ball, sparkling pools, grand outdoor chess board, putting green, kayaks, bikes, paddle boards and much more. This vacation home is the perfect rental you have been looking for. Our home accommodates 6 guests and features a .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Vacation Rentals - Little Torch Key House
RARE FIND OPEN WATER VIEWS FROM ALL ANGLES AND DECK! Located on Little Torch Key 28.5 mm Jolly Roger Estates. Meticulously designed residence with exquisite furnishings throughout home, quartz counter tops and top of the line appliances. This newly renovated home has a lovely open floorplan and entertaining feel with large outdoor spaces! Each bedroom has its own private balcony to enjoy a cup of coffee in the morning. Home design blends seamle.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 5 House Rentals
Cayo Loco - Little Torch Key House
Waterfront home with dock, high-speed WiFi, and central AC - snowbird-friendly!
Cayo Loco Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Kick back on the canal - this home is ready to host you! Relax in a friendly space with essentials like central air conditioning and a ceiling fan in every bedroom. There's plenty of room to park your boat trailer, perfect for guests that want to launch from the public boat ramp just half a mile away.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Conchanary - Little Torch Key House
Conch House on a Quiet Canal : Monthly Only
Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing. Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances, granite counters, eat at bar and large fridge. Plenty of cookware and dishes. Gas grill outside. One bedroom with a KING bed. Upstairs a small.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals
Little Torch Cottages - Little Torch Key Townhome
Luxury Ocean View 2 Bed / 2.5 Bath Townhome in the Keys
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bedroom townhomes offer breath taking bay / ocean views, a fully appointed gourmet kitchen, 2 tropical resort pools, direct access to the ocean for fishing and boating enjoyment, outdoor kitchen with a propane grilling station, memorable sunsets, close proximity to Bahia State Park, Key Deer Sanctuary, local dining, airports - all the conveniences f.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
deep water oceanside - little torch key House
Quiet and Serene - Deep Water Oceanside 30 Day Minimum Rental
kayak at house for guests use . Private two bedroom, two bath on beautiful little torch key (ocean side) on wooded canal front lot . Will accommodate large boat, with 60 amp power and cable at the dock !. House is well maintained and includes all stainless steel appliances, travetine floors in kitchen and baths and carpet in bedrooms and living room. New memory foam beds 2019 . Granite countertops in kitchen and two full bathrooms. Everyth.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Vacation Rentals - Little Torch Key Townhome
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bd townhomes offer breath taking water views, fully appointed gourmet kitchens,2 tropical resort pools, direct access to the ocean for fishing and boating enjoyment, outdoor kitchen with a propane grilling station, memorable sunsets and close proximity to Bahia State Park, Key Deer Sanctuary, local dining, airports - all the conveniences for enjoyin.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Vacation Rentals - Little Torch Key Townhome
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bd townhomes offer breath taking water views, fully appointed gourmet kitchens,2 tropical resort pools, direct access to the ocean for fishing and boating enjoyment, outdoor kitchen with a propane grilling station, memorable sunsets and close proximity to Bahia State Park, Key Deer Sanctuary, local dining, airports - all the conveniences for enjoyin.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Little Torch Cottages - Little Torch Key Townhome
Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area
Little Torch Cottages is the perfect Keys vacation get away. Our luxury inspired 2 bedroom townhomes with bay / ocean views, a fully appointed gourmet kitchen ,2 tropical resort pools, direct access to the ocean for fishing and boating enjoyment, outdoor kitchen with a propane grilling station, memorable sunsets, close proximity to Bahia State Park, Key Deer Sanctuary, local dining, airports - all the conveniences for enjoying the Key West area L.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Torchbearer - Lower - Little Torch Key House
Canal-Front Keys Escape with WiFi, AC, W/D, Patio/Firepit/Grill, & Boat Access
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Enjoy a canal-front getaway in the Florida Keys! This colorful, two-bedroom charmer offers a private slice of paradise with easy access to Key West. Entirely ground floor, this lower-level home offers a full array of amenities for outdoor living, including a firepit and lounge chairs, an im.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 6 House Rentals
Little Torch Cottages - Little Torch Key Townhome
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
Enjoy memorable sunsets, magnificent bay / ocean views and revel in all the local charm and activities the Keys have to offer. Little Torch Cottages has the perfect balance of ambiance and enjoyment you are looking for in your vacation to the Key West area. Our luxury 2 bedroom 2.5 bath townhome offer breath taking water views, a fully appointed gourmet kitchen ,2 tropical resort pools, direct access to the ocean for fishing and boating enjoyme.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Suite Blu - Key West Apartment
Suite Blu - A monthly rental apartment in a great location
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a vacationer might have. Other amenities include a vaulted ceiling, skylight, free WIFI, and digital HD cable........read more
1 Bedroom(s)
1 Bath(s) - Sleeps 2 Apartment Rentals
Sunset Harbor - Old Town Key West Location - Beautiful Property - Key West Condo
Sunset Harbor - Old Town Key West Location - Beautiful Property
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this property overlooks the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more. This 2 Bedroom, 2 Bath Condo sleeps 6, the primary suite has a king bed and connect.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals
Sago Palm - Key West Townhome
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island. The Presidents Walk properties are two level townhouses which have private courtyards on the first level and balconies on the second level. Outdoor Grill. Each bedroom has on.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals
Tailgate Key - Key West Townhome
Tailgate Key at the Key West Golf Club
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush tropical landscaping, beautiful greens and fairways of the Rees Jones designed 18-hole course. There are gorgeous views of the lake and golf course from the furnished screened outdoor deck. This gated community includes a fitness center and two beautiful pools in an Old Town Key West setting. Tailgate Key is a spacious 1,320 sq.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Awake to the Morning Reflections C437 - Key West Condo
@Key West Morning Reflections Paradise Awaits April - Sep 2022@
Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk in shower. King size bed with a flat screen TV for relaxing. The guest bedroom has a queen bed. High speed wireless internet. No attention to detai.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals
Dolphin Watch - Key West House
Dolphin Watch @ the Truman Annex
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedroom with ensuite bath and a great view of the ocean. From the second floor you can enjoy the fantastic view of the harb.......read more
4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Key West Condo - Key West Condo
Quiet, elegant, Key West Condo close to the Ocean
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inhabit the salt ponds preserve that borders this property. .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals
Key West Kokomo Condo Rental - Key West Condo
Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2/2 baths.
"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . We sleep 5 guests only. Central AC in unit, clean unit, living/dinning is open concept. Master bedroom with a king bed, with private bathroom and access to balcony. W/D in unit, full kitchen, beach towels, Reg. towels. 3 TV's, Wi-Fi. Gated community, cameras all over public areas. General parking available. Kokomo is on 3rd floor with elev.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 5 Condo Rentals
Starrs Atlantic Oasis C138 - Key West Condo
Ocean Front Key West Oasis. Tropical paradise awaits
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts of home with a fab Key West is a playground for all to enjoy, famous for its literary experts, artists, theatre and museums. Many water activit.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals
Fun In The Sun - Key West Townhome
Fun in the Sun in the Truman Annex
This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor, and is loaded with amenities such as TV's in each bedroom. The community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located about ¼ mile from one of the best beaches on the island, Fort Zachary State Park. This Presid.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
Viva Margarita! - Key West House
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold drink in hand. "Viva Margarita!" was designed to house those sun-seekers. This tropically decorated three-story home has an open living plan and a beautiful private pool area that is ideal for relaxing in your own private oasi.......read more
3 Bedroom(s)
5 Bath(s) - Sleeps 8 House Rentals
Bougain Villa, Key West - Key West House
The Key West Bougain Villa, a Monthly Vacation Rental
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Key West. This 2 bedroom and 2 bathroom house features plenty of space to accommodate guests comfortably. First-floor bedroom includes a queen-size bed & en-suite bath. Additionally, the living room sofa pulls out into a bed for extra sleepers. Upstairs bedroom features a king-size bed, twin-size trundle bed & en-suite bath. Off .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals
Mara-Villa - Key West House
**MARA-VILLA @ OLD TOWN** Private Conch Home & Hot Tub + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! MARA-VILLA is a quintessential Key West cottage that has been beautifully maintained and cared for to welcome the most discerning Key West lovers for a month in paradise. This lovingly designed conch home is exactly the Key West gem it appears to be from the street. A dreamy open living plan, two spacious bedrooms, an office, an off-street.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals
Queen Emma - Key West House
Queen Emma in the Truman Annex
This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located on a charming tree lined street in Truman Annex. The custom designed two story home has an open floor plan on the main level with separate living and dining areas. Plus a full bath and guest bedroom. | The huge porch, perfect for entertaining overlooks the large rear yard with pool and is accessed from the living area through tw.......read more
4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals
Sunset Reverie - Key West Condo
**SUNSET REVERIE @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SUNSET REVERIE is located in Sunset Marina, a gated community located on Stock Island right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the best of Old Town Key West. With your rental home at Sunset Marina you'll have plenty of space for par.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals
Blue Lagoon - Key West Townhome
Blue Lagoon in the Truman Annex
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second. | There is a lovely kitchen, dining and living room which flows out through two sets of French doors onto the covered rear deck. | The private parking is very conveniently located in the rear and is covered. | There is a side bricked patio perfect for a quiet read, or a game of corn hole! There is an outdoor grill for those p.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Townhome Rentals
Poolside Hangover - Key West Condo
Poolside Hangover @ the Truman Annex
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away from it all. Enjoy mornings out on the rear deck overlooking the refreshing community pool. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to all of the Old Town Key West attractions. The properties are also located 1 mile from one of the best beaches on the i.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals
Starshine Key West - Key West Condo
Starshine Key West in the Truman Annex
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots & pans, towels & linens, hav.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals
Villa Azura - Key West House
THE BEST place to be in Key West!
Welcome to Villa Azura - this is Enjoy this gem on a quiet lane in the award-winning gated community of the Truman Annex. Recently transformed, this beauty features a brand new kitchen with Viking appliances, gas stove, gorgeous cabinetry, wine cooler and an inviting kitchen top bar. Sink into the sweeping floorplan with tall ceilings, plenty of windows and natural light and ultra comfortable seating, lounging and dining areas on the first flo.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals
Eden @ The Annex - Key West Townhome
**EDEN @ THE ANNEX** Old Town Villa & Pool by Duval + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! EDEN @ THE ANNEX is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, EDEN @ THE ANNEX is on a quiet pedestrian lane where you'll have all of the peace and .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 5 Townhome Rentals
273 Southard Street - Key West House
Presidents Walk, 2BDR, 1.5BA Townhouse with shared pool at Truman Annex
~~7 DAY MINIMUM~~Experience the famous island city of Key West and stay at the Presidents Walk Townhouse in the private President's Lane area of the prestigious Truman Annex. Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor Beach provides a fantastic Sunshine State experience for a family or romantic couples retreat. The two-story townhouse was recentl.......read more
2 Bedroom(s)
2 Bath(s) House Rentals
Worlds End - Key West Condo
Worlds End in the Truman Annex
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area and large terraces. This beautifully decorated two bedroom, two and a half bath stately condo has wonderful views of the Atlantic Ocean and Sunset Key along the length of the Outer Mole pier which is adjacent to the beautiful Truman Waterfront Park... This community is loca.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 5 Condo Rentals
Latitude Adjustment - Key West Townhome
Latitude Adjustment at the Truman Annex
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six is located in the beautiful community of Truman Annex. This gated community offers the security and t.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals
A Low Tide - Key West Condo
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Truman Annex. | This property has recently been refreshed featuring new appliances, tvs, bedding, etc.! | It is is located 2 blocks from Duval Street and all of the Old Town Key West attractions and includes off street parking for one vehicle. | Enjoy both the front and back rear deck has outdoor dining and lounging all year lon.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals
Captains Wheel - Key West Townhome
Captains Wheel in the Truman Annex
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home featuring an open floor plan with a great rear deck for entertaining and relaxing. The master bedroom has it's own balcony and the guest bedroom features a covered porch offering plenty of outdoor living. This opportunity also includes a carport and a convenient community pool. | The President's Walk area of the Truman Annex is loca.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals