Lower Florida Keys Vacation Rentals

Blue Pelican - Comes With 6 Passenger Gas Golf Cart

Beautiful, BRAND NEW open floor plan, custom décor, private pool, gas golf cart, and ALL the amenities! KITCHEN Modern chef’s kitchen, with large island seating overlooking the beautifully appointed dining, living area, and sparkling pool. Fully stocked to the nines with chef’s quality appliances and cooking tools, as well as coordinating.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. Not just another rental property! Location is everything.!!! Our favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4. The Living/Dining area has couch,.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

**BAHAMA BRILLIANT @ THE BEACH** Colorful Private Home & Pool + LAST KEY SERVICE

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! A true island treasure, BAHAMA BRILLIANT captures the essence and beauty of living in the Caribbean. Located just two blocks from Higgs Beach, this modern home was built to a high standard and decorated in vibrant colors to enhance the tropica.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 7 House Rentals

Vacation Home

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West ha.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

"JUST OFF DUVAL" ~ Charming Condo in Center of Duval St. with Parking Space!

STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is just steps to high end art galleries, museums, The Southernmost Point of the U.S. and all best nightl.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Let us help make your dreams come true: Enjoy your tranquil view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere. You don't have to spend a fortune to enjoy a spacious, clean and comfortable Key West condo. En.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 Apartment Rentals

Vacation Home

**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two s.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

**LA VIE EN ROSE @ BEACHSIDE** Modern Home / Large Pool + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! LA VIE EN ROSE is a classic mid-century modern home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. As the lyrics to that sweet love song go, you'll be in 'a world apart'. You'll also be clos.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Oceanfront Oasis Summ

Summary: A beautiful oceanfront suite located at the best marina in the Keys. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel. Our prope.......read more

1 Bedroom(s)
3 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

DESIGN YOUR OWN WATER ADVENTURE

A well appointed and renovated 36' Morgan Out Island Sloop, at ANCHOR with no dock, north of KW harbor . 2 guest MAXIMUM. Water and coffee complimentary. Water taxi transport is available for checking in and out between 5-7pm and 10-12 DISCOUNTED FOR MY GUESTS for insertion and extraction.For transport outside of those windows is a COST item fo.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 2 Boat Rentals

Vacation Home

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 House Rentals

Vacation Home

Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And Atlantic or Gulf

Welcome to Prime Time 2! This charming waterfront duplex is located on Big Pine Key and offers quick open water access and a relaxing environment. Plenty of seawall for your boat and it's a short boat ride to world class fishing. Relax in the screened porch while reading a book or enjoying your favorite beverage! There's plenty to do in the Keys,.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 House Rentals

Vacation Home

Fishermen`s Paradise

Newly remodeled and with a brand-new dock, this spacious three-bedroom, four-bathroom home has a fantastic pool and amazing open-water views from every vantage point. Nestled in the backcountry on Big Pine, you'll enjoy the modern conveniences of this 2,000-square-foot elevated home while reveling in the natural areas surrounding it. The newly reb.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access To Atlantic or Gulf

Welcome to Prime Time! This lovely canal front duplex is located on Big Pine Key and offers a fun, tropical vibe and open water access. Dock your boat along the sea wall and enjoy fantastic fishing only minutes away. Relax on the screened porch while enjoying your morning coffee or favorite cocktail as the boats go by! There's plenty to do in the .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Special Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut

Saturday - Saturday Monthly Rental Open Lobster Dates July 1-31 or Aug 1-31 (No breaking months) This keys heated pool retreat is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world . The gem like waters are .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve

Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wake up to Key Deer in your back yard. Only 30 miles from Key West and Duval Street. Concrete, step-down dock. Bring your boat. Great fishing and Diving. Bahia Honda Beach close by. Comfortably sleeps 6 plus two full sized sof.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 House Rentals

Vacation Home

Keys Getaway

This spacious two-story Canal Front Home is located in Pine Channel Estate and offers fantastic boating access to some of the best fishing and diving/snorkeling spots in the Lower Keys. Tropical living at its best. The large screened porch is overlooking the canal. Master bedroom and loft sleeping area are on the second floor and have a queen bed .......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

3 bedroom accommodation in Big Pine Key

You'll relish your Florida Keys stay in this stilted canalfront home with ground-level guest suite, laundry and storage. There's a spacious, fully equipped kitchen with stainless steel appliances and an office setup for all your telecommuting needs. There are two queen bedrooms and two full bathrooms in the main floor, as well as a daybed with trun.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 charge in the winter. Over 200’ of concrete dock.......read more

5 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals

Vacation Home

4 bedroom accommodation in Big Pine Key

Brand 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 .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Waterfront Keys Cottage "Del Boca Vista"

NEW VACATION HOME LISTING! This newly renovated beach style waterfront home boasts sunset views and is tastefully decorated in an island style. Soaring vaulted ceilings in the great room complement the open concept floor plan which opens out to a large screened porch overlooking the 70’ wide canal waterway below. The master bedroom has ensuite b.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

SPECIAL TROPICAL POOL GETAWAY

This keys pool retreat is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront pool home has it all. This fantastic community is one of the most unique places in the world . This gated home sets on a huge property with plenty of room for your boats, trailers and cars. Neatly furnished you have the.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

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 House Rentals

Vacation Home

Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!

Beautiful, newly redone home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Canalside docking for your boat. Amazing sunrises on the private porch deck. New furniture. This home offers a wonderful opportunity for relaxation & enjoyment of many water sports and activities in the beautiful, tropical FL Keys. Kayaks,.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Tropical Waterfront Pool Getaway

This keys pool getaway is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. The gem like waters is the home of an almost endless variety of fish and marine life. In minutes you can explore the fantastic back.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 House Rentals

Vacation Home

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 April.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 4 House Rentals

Vacation Home

Waterfront Home in The Fabulous Florida Keys!

PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. We’d like to share our home with you. It’s a very spacious and clean 2 bedrooms, 2 bath home with an over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap aroun.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm

The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fishing coupled with backwater bonefish and permit fishing rivaled to none. The Looe Key National Park, famous for it's crystal clear water, brilliant tropical fish and live coral is only 4 miles off Big PIne Key, great for diving or.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Nice 3 Bedroom / 2 Bath Canal Home in Big Pine Key

Florida "Keys Living", the way it should be!! Located in Doctor`s Arm, a very nice and quiet neighborhood. This 3 Bedroom / 2 Bathroom home that sleeps up to 8, is comfy, cozy and delightful. The fully-equipped kitchen is a pleasure to cook in for your family. A wrap-around upstairs deck and a screened-in porch just off the Dining Room, gives plen.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT

Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preserve the beauty and peacefulness of Big Pine Key. PLEASE CLICK VIEW MORE BELOW TO VIEW CANCELLATION POLICY My property is a rare find in the lower keys. Nestled in the middle of the Key Deer Wildlife Refuge. This house is located .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 House Rentals

Vacation Home

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 House Rentals

Vacation Home

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 House Rentals

Vacation Home

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 sun.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals

Vacation Home

***VERY NICE 3 BR / 2 BA CANAL HOME IN BIG PINE KEY!***

3 Bedroom/2 Bath Canal Home in Big Pine Key! Great boating location and easy access to open water. The home is very clean, well appointed and comfortable. Just bring yourself, your boat and some friends...you will be happy you picked 5 O'Clock Somewhere for your Florida Keys vacation home!.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 con.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 12 House Rentals

Vacation Home

New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel

Welcome to our new spacious 3 bedroom 2 full bath home on an 80 foot wide deep water canal with a 60 foot dock only 1500 feet from the peaceful open waters of Pine Channel. The dock is equipped with a ladder and ample fenders and cleats to secure your boat. Our canal enters Pine Channel south of the Overseas Highway Bridge ,so any guests with sailb.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Canal Front Pool Home

Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars and trailer. Open floor plan also includes a game room with ping pong, foosb.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm.

2 Bedroom 2 Bath Canal Front home on fenced lot with great boating access to back country or ocean side through Bogie Channel. Amenities include new A/C, upgraded master bath, & docking for your boat. Large screened in porch is perfect for sipping cocktails and watching the sunset. The house is located on Big Pine Key home to hundreds of friendl.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Saltwater Paradise in a Wildlife Preserve

Sleeps 7 comfortably, up to 11, fully equipped kitchen, loft, front and rear porches with spectacular views, best sunset ever, loft for reading relaxation, cable television, paddle boat, 70 ft dock with fish cleaning station. Boat no bigger than 27 ft. Deer will come up to the house, nature trails, blue water lagoon, cycling path, drive to Old Key .......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Open Water and Sunset Views Pool House in the Florida Keys

4 bedroom 2 bath house on Big Pine Key. Property includes 70' dock with biat lift, double lot, heated swimming pool, fire pit, BBQ, ice machine, downstairs storage, kayaks, paddleboards, cornhole boards and more! Master Bedroom upstairs with King Bed, 3 bedrooms downstairs. Bedroom 1 - Queen Bed, Bedroom 2 - 2 Singles, Bedroom 3 - 2 Singles. Op.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

New listing 3bd/2bt Sleeps 8 "Sunset Paradise Villa" on canal Big Pine Key

*BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a 3 Bedroom/2 Bath canal/water front tropical villa that sleeps 8+ located in beautiful Tropical Bay Estates on Big Pine Key in the Florida Keys. This remodeled and newly furnished villa with Sunset views from screen patio that is loaded with amenities .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home