Lower Florida Keys Vacation Rentals, Homes & Cottages
Book Your Lower Florida Keys Florida Vacation Rental Homes Here and Save! Many to choose from!
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.
Vacation Rental
Palms Resort - Green 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 clos.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 8 SUGARLOAF KEY House Rental
Sugarloaf Shores
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 are.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 Sugarloaf Key House Rental
Vacation Rental
Beautiful 3/2 Sleeps 10. ALL ROOMS Waterfront 3/2 POOL
Casa Verde - the open water views from every room of this gorgeous home will leave you breathless! This is truly an escape from the hustle bustle. Located on direct open water in a very quiet neighborhood, you can enjoy many resort activities - without ever leaving home! Snorkel, fish, or swim right off the deck, in the warm, crystal-clear waters.......read more
4 Bedroom(s)
2 Bath(s) - Sleeps 10 Sugarloaf Key House Rental
Vacation Rental
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 avail.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 5 Cudjoe Key House Rental
Vacation Rental
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 CHI.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 Cudjoe Key House Rental
Vacation Rental
Blue Chill Vacation!!!
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 'over.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Cudjoe Key House Rental
Vacation Rental
Seascape Vacation!!!
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 .......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 Cudjoe Key House Rental
Vacation Rental
"Seas The Day" in Cudjoe Key
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 defi.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Cudjoe Key House Rental
Vacation Rental
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-i.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Cudjoe Key House Rental
Vacation Rental
Catch n' Relax in The Keys!
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 Ar.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Cudjoe Key House Rental
Vacation Rental
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 y.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Cudjoe Key House Rental
Vacation Rental
Calico Jack Hideaway
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 storag.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Cudjoe Key House Rental
Vacation Rental
Cozy, Perfect Conch Cottage!
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,.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 Cudjoe Key House Rental
Vacation Rental
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
Studio
1 Bath(s) - Sleeps 6 Cudjoe Key Campground Rental
Vacation Rental
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 f.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 6 Cudjoe Key Campground Rental
Vacation Rental
CUDJOE ESCAPE PROPERTY
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 th.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 cudjoe key House Rental
Vacation Rental
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 .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Cudjoe Key House Rental
Vacation Rental
Bring Your Boat
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 avai.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Cudjoe Key House Rental
Vacation Rental
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 Sle.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 Big Pine Key House Rental
Vacation Rental
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.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 5 Big Pine Key House Rental
Vacation Rental
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-n.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 4 Big Pine Key House Rental
Vacation Rental
Serenity on San Remo
***Pool just completed! Updated photos when the landscaping is done!*** Enjoy unmatched privacy and serenity during your stay at this gorgeous canalfront 3 bedroom/3 bathroom pool home nestled near the end of Doctors Arm on Big Pine Key. Brand new custom concrete pool with heater for those cooler fall and winter nights. There are clear 40-foot-w.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 8 Big Pine Key House Rental
Vacation Rental
3 bedroom accommodation in Big Pine Key
***New rental for summer 2022!** Fantastic boating from this 3 bedroom, 2.5 bathroom canalfront pool home in one of the Lower Keys' best boating neighborhoods, Pine Channel Estates. On a clear, deep canal just a few minutes from the channel, giving you easy access to the ocean or backcountry. You'll enjoy a quiet and cool vacation inside this so.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 8 Big Pine Key House Rental
Vacation Rental
2 bedroom accommodation in Big Pine Key
Enjoy Big Pine Key's peace and quiet from the canalfront screened porch of this 2 bedroom / 2 bathroom home in of Port Pine Estates, nestled deep in the heart of the Florida Keys National Key Deer Refuge. This well-maintained home on the gulf side of the island is nicely furnished and stocked with everything you need for your low-key monthlong vaca.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
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. Excel.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
PARADISE IN YOUR HANDS
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. Ke.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
Big Pine Latitude Adjustment
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’ o.......read more
5 Bedroom(s)
3 Bath(s) - Sleeps 10 Big Pine Key House Rental
Vacation Rental
4 bedroom accommodation in Big Pine Key
**Gorgeous custom pool and spa on the way for winter 2023!** Like-new 4-bedroom, 3-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key with a custom concrete pool and spa scheduled for completion in fall 2022. 60-foot concrete dock with large fender piles for your big boat. Convenient steps down into t.......read more
5 Bedroom(s)
3 Bath(s) - Sleeps 10 Big Pine Key House Rental
Vacation Rental
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 c.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 12 Big Pine Key House Rental
Treasure in the Pines
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.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Big Pine Key House Rental
Vacation Rental
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.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Big Pine Key House Rental
Vacation Rental
Prince`s Keys Serenity
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 Apr.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
Castaway on the Keys
Enjoy unobstructed open water views of Bogie Channel and No Name Key from this brand-new resort-style home featuring 80 feet of canal dockage, a huge porch and custom concrete pool. With more than 2,800 square feet under air, there's plenty of room for the entire family during your Florida vacation at Castaway on the Keys. Huge living area with.......read more
4 Bedroom(s)
4 Bath(s) - Sleeps 10 Big Pine Key House Rental
Vacation Rental
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 d.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
2 bedroom accommodation in Big Pine Key
This is a minimum 28-day rental per county ordinance. 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 kitc.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 4 Big Pine Key House Rental
Changes in Latitude
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 per.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 8 Big Pine Key House Rental
Reel NV
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 .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
Perfect Keys Getaway
Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite counters and stainless appliances, washer & dryer. Master bedroom with king bed, second bedroom has a queen size bed. Sofa in living room converts to another queen bed if needed. There is a nice screened porch overlooking the canal.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Paradise Retreat ~ BPK
Paradise Retreat ~ BPK
~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 Maratho.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Big Pine Key House Rental
Vacation Rental
5 bedroom accommodation in Little Torch Key
Beautiful & well-appointed 5 bedroom / 2.5 bathroom home with excellent water access on Little Torch Key via Pine Channel, just minutes to the open Atlantic & short ride to Looe Key National Marine Sanctuary. Double lot with 120-foot seawall. Large outside sitting and dining area. Gas grill. Plenty of parking. Water access via Pine Channel, one .......read more
5 Bedroom(s)
3 Bath(s) - Sleeps 10 Little Torch Key House Rental
Vacation Rental
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 f.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 6 Little Torch Key Mobile home Rental
Little Torch Hidden Gem
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.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Mobile home Rental
Vacation Rental
Jolly Roger Retreat!
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 .......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Little Torch Key House Rental
Vacation Rental
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 .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Little Torch Key House Rental
Conchanary
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 frid.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 Little Torch Key House Rental
Vacation Rental
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, clos.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Townhome Rental
Vacation Rental
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 liv.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 little torch key House Rental
Vacation Rental
Water View Town home
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 proximit.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Townhome Rental
Vacation Rental
Water View Town Home
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 proximit.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Townhome Rental
Vacation Rental
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.......read more
3 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Townhome Rental
Vacation Rental
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 .......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Little Torch Key Townhome Rental
Vacation Rental
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 vaul.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 2 Key West Apartment Rental
Vacation Rental
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 t.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental
Vacation Rental
SAGO PALM in the Truman Annex
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.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 4 Key West Townhome Rental
Vacation Rental
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.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental
Vacation Rental
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun. KWF
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 .......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West Condo Rental
Vacation Rental
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 bat.......read more
4 Bedroom(s)
3 Bath(s) - Sleeps 8 Key West House Rental
Vacation Rental
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 inh.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental
Vacation Rental
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 co.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 5 Key West Condo Rental
Vacation Rental
Ocean Front Key West Oasis. Island Tones, Charming Historical Downtown area.
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.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental
Vacation Rental
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 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 op.......read more
3 Bedroom(s)
5 Bath(s) - Sleeps 8 Key West House Rental
Vacation Rental
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 ex.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West House Rental
Vacation Rental
**MARA-VILLA @ OLD TOWN** Private Conch Home & Hot Tub + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 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 appear.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West House Rental
Vacation Rental
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 .......read more
4 Bedroom(s)
3 Bath(s) - Sleeps 8 Key West House Rental
Vacation Rental
**SUNSET REVERIE @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 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 b.......read more
3 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental
Vacation Rental
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.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental
Vacation Rental
VILLA AZURA 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.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West House Rental
Vacation Rental
**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 t.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 5 Key West Townhome Rental
Vacation Rental
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 Sun.......read more
2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West House Rental
Vacation Rental
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.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 5 Key West Condo Rental
Vacation Rental
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 i.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental
Vacation Rental
A LOW TIDE in Truman Annex
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 o.......read more
2 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental
Vacation Rental
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 include.......read more
2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental
Vacation Rental
SUN, SEA, AND SKY in the Truman Annex
Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of l.......read more
1 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental