Big Pine Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Big Pine Key, Florida on RentalSaver.com!

Big Pine Key Rentals

From $305 per night (USD)
VRBO
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tradewinds Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $305 per night (USD)
VRBO
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Expedia
Beautiful Keys Getaway! Located on deep water canal for quick access to
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. ...
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Expedia
From $601 per night (USD)
VRBO
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with, 50" TV, refrigerator, fire pit area, an ...
From $601 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Luxury and Lovely Water Front House
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of M ...
From $626 per night (USD)
Expedia
From $393 per night (USD)
VRBO
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This Private Canal front Pool/TIKI home with Dock, sits in Port Pine Heights BIG PINE KEY FL. See key deer every day wa ...
From $393 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Amazing Pool & Canal Ground Level Home, Ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. (POOL HEAT AV ...
From $336 per night (USD)
Expedia
$New listing 3bd/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $235 per night (USD)
VRBO
New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Bridge restriction***BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a ...
From $235 per night (USD)
VRBO
From $178 per night (USD)
Expedia
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom 2 bath stilt home with large screened in porch overlooking canal and lush tropical coconut palms. Boat dock Wi ...
From $178 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Newly Remodeled Corner House on the Water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-be ...
From $223 per night (USD)
VRBO
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Expedia
PARADISE IN YOUR HANDS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful clean and spacious home. Relax on your deck or take your boat out, canal goes out to the gulf or ocean to do s ...
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Expedia
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VRBO
Easy access to the Ocean and Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Leave your worries and enjoy the island life style. I promise you that this will be your favorite gateway. Beautiful san ...
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VRBO
From $136 per night (USD)
Expedia
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $136 per night (USD)
Expedia
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VRBO
Lower Keys on quiet canal front w/boat lift, screened-in porch & Pets Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your own relaxing quiet oasis. Fenced in yard that offers privacy with the foliage beyond the banana palms an ...
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VRBO
From $377 per night (USD)
Expedia
Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Finding Remo—a premier, private, luxury retreat nestled within the Great Heron and Key Deer National Wildlife ...
From $377 per night (USD)
Expedia
From $202 per night (USD)
VRBO
🌴 TROPICAL RETREAT 🌴 RV in the Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tropical retreat in the heart of Florida Keys. Relax island-style in this private updated RV - just 30 miles from Key We ...
From $202 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Modern multi story waterfront home, 30 minutes from Key west.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
One of a kind custom modern home, brand new all concrete construction. Multi level exclusive residence. 3 floors of livi ...
From $416 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Tropical Caribbean Paradise with pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Note: This is a new unit the other RV from the reviews was damaged by Irma and this is the NEW replacement unit it is AW ...
From $230 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Big Pine Key Paradise Canal front fenced yard.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WINTER 2026 OPEN Canal front fenced in home w/dock, boat ocean access. 28 Night Min Stay, WiFi Full kitchen Fully furn ...
From $240 per night (USD)
VRBO
$DREAMS COME TRUE - 75' DOCK - 250 ' TO OPEN CHANNEL\nBIG PINE KEY FL$
From $183 per night (USD)
VRBO
DREAMS COME TRUE - 75' DOCK - 250 ' TO OPEN CHANNEL\nBIG PINE KEY FL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 75 foot dock only 250 feet from ...
From $183 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful, newly redone home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Canalside ...
From $330 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THE ADVENTURER'S RETREAT - BIG PINE KEY BUNGALOW IS YOUR HOME AWAY FROM HOME WHERE YOU CAN RELAX AND ENJOY THE CENTRALIZ ...
From $234 per night (USD)
VRBO
From $277 per night (USD)
VRBO
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. Oceanfro ...
From $277 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Beautiful Canal Front Heated/Chilled Pool 4 Bdr Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Modern updated 4 bedroom 2 bath stilt home centrally located in Big Pine. Large heated / chilled swimming pool with ta ...
From $233 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Island Sunrise Resort- 3 acre estate with open water sunrises.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Island Sunrise Resort is a 3 acre open water estate. Enjoy the 250' dock, pool, spectacular views of distant islands and ...
From $594 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Mickey and Lynn's House of Windows
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the ...
From $403 per night (USD)
VRBO
From $516 per night (USD)
VRBO
Family friendly canal home,150 ft dock, easy access to Atl & Gulf
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxin ...
From $516 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fish ...
From $177 per night (USD)
VRBO
From $258 per night (USD)
VRBO
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preser ...
From $258 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Lower Keys Retreat..... Come.... Relax in Paradise!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful home located in Eden Pines, a Peaceful subdivision on Big Pine Key has the best of everything. Furnished ...
From $318 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Paradise Retreat ~ BPK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
~3/2 home with heated pool located on large ,private and fenced property. Screened room and patio deck. Privacy is key t ...
From $216 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Canal Front Home in Big Pine Key with Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedrooms, 2 Baths, Sleeps 6 The 3 bedroom 2 bath canal front home is located in a quiet neighborhood located on Big P ...
From $282 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*WINTER 2025 now available!!! (Dec 2025 - Mar 2026). Book quickly! Cozy, clean, canal front home is located in a quiet ...
From $160 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Canal Front Home With Pool And Hot Tub
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Terrific tropical getaway for rent!! 2 Bedroom 3 full bath canal front home with large in ground pool, hot tub and 60 f ...
From $336 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Beautiful waterfront home with central AC, dock, lovely balcony & patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Big Pine Key Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $200 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Charming 2-bedroom 2- bath home located in the middle of The Key Deer Refuge.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can re ...
From $362 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Christmas in the FL Keys!!! Stunning sunsets, beaches 10 min away, Fishing!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3bdrm, 2 bath house with stunning sunset views, beautiful Bahia Honda State Park 10 min away, other beaches all within 3 ...
From $225 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Heavenly Hideout - Your Waterfront Pool Home - Escape to the Florida Keys!! Escape to paradise in this beautiful vacati ...
From $326 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Big Pine Waterfront Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our charming canal-front bungalow in the Florida Keys! This delightful rental offers an unforgettable experie ...
From $270 per night (USD)
VRBO
From $407 per night (USD)
VRBO
3-bedroom house in Lower Keys with Hot Tub, Sleeps 10+, Pet Freindly
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Discover the beauty of the Lower Keys in Perfect Location to access Bay and Ocean Side from this 3-bedroom house. This g ...
From $407 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Airstream Travel Trailer
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Airstream's most popular travel trailer is 27 feet long and features wrap-around windows, a queen bed, two AC units, a 4 ...
From $295 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Big Pine Turtle House
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to Big Pine Turtle House, a warm haven nestled near the open ocean and a tranquil canal access. 50 ft. dock on a ...
From $258 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Dog-friendly home with waterfront views, a pool & Wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tropical Valhalla Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $310 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Charming 2-bedroom house in beautiful Big Pine Key with canal access and lift
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom house in Big Pine Key. This terrific property features a king bed and a queen bed, ...
From $220 per night (USD)
VRBO
From $178 per night (USD)
Expedia
SOLD - NO LONGER AVAILABLE Serene Canal home in the Heart of the Keys
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Thirsty Turtle is nestled in the heart of the Florida Keys, Whether you're looking to unwind, explore the outdoors, ...
From $178 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Lovely dog-friendly home near the ocean with hot tub & grill
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Octopus Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $219 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Beautiful 2 Bedroom Pool Home On Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous canal front 2 bedroom 2 bath pool home located on Big Pine Key. Excellent boating to the Gulf or the Atlantic w ...
From $312 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Reel Paradise | Fabulous sunsets from this canalfront 2 bed/2 bath on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cozy 2 bed/2 bath canalfront monthly rental nestled in the natural beauty of the Big Pine Key. Located in the quiet Eden ...
From $202 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Escape to Paradise, a 3-bedroom canal home on Big Pine Key.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your idyllic getaway on Big Pine Key, where tranquility meets adventure! This spacious 3-bedroom, 2-bathroom ...
From $249 per night (USD)
VRBO
From $137 per night (USD)
VRBO
Relaxing Florida Keys canal front home in nature preserve
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Kokomo Palms! This relaxing getaway is a single family, canal front home located on Big Pine Key. It offers ...
From $137 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wa ...
From $159 per night (USD)
VRBO
From $836 per night (USD)
VRBO
Awesome Open Water View at Blue Heron Estate
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
15 Acre Open Water Estate. Four bedrooms each with their own private bathroom. Large pool. Breathtaking views of the sun ...
From $836 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Banana Republics - Located in Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Quaint 577 s.f. (1) Bed home on concrete piers. Built in 2015 and also has a balcony and deck. Located on Big Pine Key y ...
From $160 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Waterfront, Bayview home with dockage sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Multiple month rentals welcomed and encouraged. Amazing upstairs 2 bedroom, 1 bathroom, downstairs 1 bedroom 1 bathroo ...
From $346 per night (USD)
VRBO
From $232 per night (USD)
Expedia
CASA COCO BY THE CANAL!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the beautiful Canal-facing newly rebuilt rambler home. Located at Big Pine key that is easily accessible to K ...
From $232 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Waterfront home with boat dock, 2 kayaks, 2 bikes, AC & W/D - dog-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunset Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $177 per night (USD)
VRBO
From $201 per night (USD)
Expedia
New Beach House-Boat & Dog Friendly 30 mins Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Brand new! Pet friendly, quiet and clean beach house. Located on Big Pine Key. Only minutes from boat ramps, white sand ...
From $201 per night (USD)
Expedia
From $462 per night (USD)
VRBO
SEA EVERYWHERE! Open Water & 2 Boat Basins!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Beautiful open-water views of the Bahia Honda bridge from nearly every room! Key deer grazing daily in your yard. Tw ...
From $462 per night (USD)
VRBO
From $575 per night (USD)
VRBO
SEA FOREVER! Gorgeous Ocean-Front Paradise!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This feels like your own private resort. Two tiki huts cover lounge chairs and a 13-foot shuffleboard court. The pool an ...
From $575 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Tropical 5BR Paradise, Private Pool, Hot Tub, Canal Access – Sleeps 12
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Your unforgettable Big Pine Key adventure starts here! This spacious 5-bedroom, 3-bath private retreat sleeps 10–12 gues ...
From $440 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Cozy Cottage in Big Pine Key – 35 Min to Key West, Pool & Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the perfect balance of comfort, charm, and location in this cozy cottage on Big Pine Key, just a short 35-minut ...
From $310 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Water Views / Heated Swimming Pool / Hot Tub / Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New swimming pool ( with option to be heated for a fee ) and hot tub with amazing water views. Welcome to Paradise! Stay ...
From $229 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Boater's Paradise with Boat Dock / Quick Open Water Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with a boat dock. Steps away from ocean wat ...
From $209 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Big Pine Retreat will leave you wanting to come back year after year!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This newly remodeled home is cozy, yet spacious. Situated in the Whispering Pines neighborhood you will experience relax ...
From $273 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Beautiful Open-Water Property
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This well-appointed 3-bedroom x 3 full-bathrooms seaside property faces west on the open sea (<1mi to the next island) w ...
From $464 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
DO NOT BOOK STAYS THAT BOOK INTO 2 MONTHS WITHOUT APPROVAL (example: 7/25-8/10). This property is only allowed 1 rental ...
From $317 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Escape the Ordinary and Experience Island Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Tarpon Retreat is a luxurious vacation rental home, nestled in an island paradise located in the Big Pine Key Deer Refug ...
From $215 per night (USD)
Expedia
From $520 per night (USD)
VRBO
3-bedroom on water. Cable, WiFi, AC, Hot tub, Dock. Feb & March 2026 Available!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom waterfront Big Pine Key retreat. This brilliant house features 2 king beds and 1 ...
From $520 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Tropical Canal-front Cottage in the Lower Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Snapper Villa is the perfect destination for those looking for a tropical getaway. Set on a canal-front in the Big Pine ...
From $422 per night (USD)
Expedia
Click For Pricing
VRBO
Fill the Day with Sun & Fun!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Do everything or nothing at this Florida Keys 2br/2ba! Relax on the screened porch, kayak in the canals or take a boat r ...
Click For Pricing
VRBO
From $288 per night (USD)
VRBO
Nature's Paradise - Inground Pool - GREAT MONTHLY RENTAL RATE
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Contemporary home with cathedral ceilings on corner canal, featuring a 40-foot boat dock with powered davits and 31 foot ...
From $288 per night (USD)
VRBO
From $232 per night (USD)
VRBO
Amazing Paradise House Canal Front with access to Atlantic and Gulf.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
BEAUTIFUL KEY PROPERTY !!!!SEASONAL Monthly Rental only, built in 1990, Big Pine Fishing house is a 2 BR, 2 BA, with a l ...
From $232 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Waterfront Oasis in the Keys
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Waterfront oasis with meticulous finishes and a vibrant modern interior giving you the feeling of an upscale resort. Fro ...
From $446 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Escape to the Florida Keys to this tropical canal-front home with boat dockage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to a tropical sanctuary at this beautifully remodeled, fully furnished ground level island home located in the Fl ...
From $383 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Easy access to beautiful Keys water & a short drive to Key West fun!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Easy access to Lower Keys Paradise. Conveniently located on Big Pine Key - close to the bait shop, dive shop. local rest ...
From $236 per night (USD)
VRBO
From $257 per night (USD)
VRBO
🐠 HEATED SWIM SPA / OPEN WATER VIEWS / BOAT DOCK / LUXURIOUS / BUILT IN 2023🐬
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to boater’s dream location with 45 Ft of concrete dockage for boat. Large canal with QUICK Gulf & Ocean access t ...
From $257 per night (USD)
VRBO
From $1076 per night (USD)
VRBO
Boat dockage & a great Gulf-front Big Pine retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Tiki Beach House, your exclusive 4-bedroom, 3-bathroom retreat nestled on the Gulf side of the enchanting Big ...
From $1076 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You have found it. So quiet. So beautiful. On Bogie Channel. One mile from No Name Pub. Only 30 miles from Key West! FU ...
From $479 per night (USD)
VRBO
From $242 per night (USD)
VRBO
Perfect getaway keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite coun ...
From $242 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Excellent boating location-65 ft frontage on deep canal
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Excellent location 2 bedroom 2 bath home with a 65 ft sea wall on wide canal in Big Pine Key. This is a perfect location ...
From $188 per night (USD)
VRBO
From $178 per night (USD)
Expedia
LARGE LOT & RV A Fisherman Camp
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
30 miles to Key West! A classic Keys RV. RV is a 2010 5th wheel in original condition w/bedroom, 2 flat screen tv’s & fu ...
From $178 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Beautiful 2/2 Waterfront Designer Home for your family vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the best that the keys has to offer in this custom built designer home that has everything to make your vacation a ...
From $159 per night (USD)
VRBO
From $1800 per night (USD)
Expedia
Waterfront Beach Houses with Dock & Heated Pool!
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront homes with 200 foot dock for your boat. Two exclu ...
From $1800 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Waterfront Cozy Cottage with Boat Ramp & Dock!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your ...
From $528 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Waterfront home with dock, high-speed WiFi, and central AC - snowbird-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cayo Loco Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $273 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Gorgeous Beachfront Home with a pool. Water views from every direction.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Step into your own island paradise! Welcome to this 5 bedroom 3 bath home. Featuring a large private beach with a heated ...
From $545 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Dates available Oct, Nov, Dec 2023
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Flor ...
From $236 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Beautiful House on Canal - minutes to the Atlantic, no bridges
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges. 60' of canal fr ...
From $317 per night (USD)
VRBO
From $2675 per night (USD)
Expedia
A Tropical Luxury Getaway, Your own private resort!!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open wate ...
From $2675 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Your Best Fishing And Relaxing Experience! 2/2 Waterfront Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This secluded waterfront home is on a quiet dead-end street at mile marker 25. It offers all the amenities you need to e ...
From $223 per night (USD)
VRBO
From $350 per night (USD)
Expedia
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $350 per night (USD)
Expedia
Click For Pricing
VRBO
Close to Key West Canal-front retreat w/ kayaks located on Little Torch Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Introducing Aj’s Hideout – Welcome to your idyllic retreat in Little Torch Key, nestled in the heart of a charming fishi ...
Click For Pricing
VRBO
From $289 per night (USD)
Expedia
JUNE-AUG 2025 DISCOUNT! - 2 Bedroom FL Keys Canal Home - Great Boating Access!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out ...
From $289 per night (USD)
Expedia
Click For Pricing
VRBO
Keys Living Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable Cottage in the heart of the Fabulous Florida Keys! Only 30 minutes from Key West and 15 minutes from Bahia H ...
Click For Pricing
VRBO
From $427 per night (USD)
Expedia
Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
There's no better place to experience the magic of the Florida Keys than this bright and remodeled three-bedroom getaway ...
From $427 per night (USD)
Expedia
From $838 per night (USD)
VRBO
Waterfront Captain House with Boat Basin & Ramp!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property ...
From $838 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Private Florida Keys Escape w/ Pool, Dock, Tiki Bar – Pet Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Little Torch Treasure – Private Pool, Tiki Bar, Dock, and More in the Florida Keys Welcome to Little Torch Treasure, you ...
From $477 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Secluded Keys Escape | 3BR Gated Canal-Front Home with Open Water Views & Bay Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Canal-Front Vacation Home with Bay Access – Big Pine Key, Florida Discover your perfect Florida Keys escape in t ...
From $317 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Open water view, boat dockage, 4 bedroom Home in Big Pine Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Welcome to The Grand Tortuga, your luxurious retreat in Big Pine Key, Florida! This recently renovated, waterfront haven ...
From $599 per night (USD)
VRBO
From $621 per night (USD)
VRBO
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy memorable sunsets, magnificent bay / ocean views and revel in all the local charm and activities the Keys have to ...
From $621 per night (USD)
VRBO
$HEAVENLY PARADISE-60' DOCK SO CLOSE TO OPEN WATER---\nLITTLE TORCH KEY$
From $161 per night (USD)
VRBO
HEAVENLY PARADISE-60' DOCK SO CLOSE TO OPEN WATER---\nLITTLE TORCH KEY
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 60 foot dock only 2 minutes fro ...
From $161 per night (USD)
VRBO

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Results: 127 Rentals