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 $553 per night (USD)
VRBO
Old Florida Style, wrap around porch, boat basin for dockage, open water
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will love spending time at this lovely home located on Little Torch Key, with Sunrise view, large property with boa ...
From $553 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Canal Front Paradise! Just a few yards from open water!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak where dolph ...
From $145 per night (USD)
VRBO
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 $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 $1194 per night (USD)
VRBO
300’ Private Beach, Pool & Rooftop w Panoramic Ocean Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Minty Mermaid Looking for the perfect estate to host an exclusive beach wedding? The Minty Mermaid is undoubtedly the ...
From $1194 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Cheerful Tiny House, 35 min to Key West, comes with free pool and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and adorable deers! This is a ...
From $177 per night (USD)
Expedia
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 $316 per night (USD)
Expedia
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $316 per night (USD)
Expedia
From $200 per night (USD)
VRBO
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)
VRBO
From $137 per night (USD)
Expedia
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)
Expedia
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 $726 per night (USD)
Expedia
Newly renovated cozy and spacious beach house with breathtaking ocean front
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Spectacular ocean front home awaits you in Big Pine Key. Cozy family getaway with breathtaking ocean view and over 450 f ...
From $726 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Ocean Front Beach Home on Semi Private Island Only Accessible by Boat
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Tune out the noise and escape to this rustic Florida Keys island retreat only accessible by boat! Ocean views that never ...
From $573 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 $285 per night (USD)
VRBO
Fishing, swimming and relaxing on the porch in Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. Its located in Tropical Estates, a quiet u ...
From $285 per night (USD)
VRBO
From $1078 per night (USD)
VRBO
4 Bedroom 3 Bath Water View Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our luxury inspired water front resort community is the perfect Keys vacation get away. We offer a fully furnished 4 bed ...
From $1078 per night (USD)
VRBO
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 $393 per night (USD)
Expedia
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $393 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
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Expedia
The Happy House will be your Happy Place
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This house has a seawall where you can dock your boat in a deep canal. It over looks a protected preserve where you can ...
Click For Pricing
Expedia
From $316 per night (USD)
VRBO
LiL Piece of Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
ALL BOATERS!!! ALL FISHERMAN WELCOME This 3 bedroom, 2 bathroom home has everything you need. Built in 2019 and comfort ...
From $316 per night (USD)
VRBO
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Expedia
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
Expedia
From $700 per night (USD)
VRBO
Big Pine Key! 3 bedroom house 2 bath sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large outdoor kitchen , sitting area, corn hole activity area, swim spa , entertainment ( outdoor tv & outdoor speakers ...
From $700 per night (USD)
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 $303 per night (USD)
VRBO
Keys Paradise 2-bedroom, 2-bath with heated pool & direct access to the Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your dream rental home in the enchanting Florida Keys. This exquisite 2-bedroom, 2-bathroom home is nestled a ...
From $303 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Florida Keys Water Front Vacation Home with Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3-BR waterfront house with pool that is located directly on an ocean canal with easy access to the Gulf of Mex ...
From $297 per night (USD)
Expedia
From $215 per night (USD)
VRBO
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)
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
From $139 per night (USD)
VRBO
20 ft from your room to a clean canal full of fish and lobsters and crabs.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Only 10 minutes to bahia honda beach, rated top ten every year. 35 min to key west. 3 hrs to miami, a great sight seeing ...
From $139 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. There's a L shaped floating dock that can host a ...
From $433 per night (USD)
Expedia
From $237 per night (USD)
VRBO
LittleTorch Key3/2 canal home with quick ocean access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly Renovated Canal home in Jolly Roger Estates. Large corner lot with room for boat trailer parking. End canal locat ...
From $237 per night (USD)
VRBO
From $2234 per night (USD)
Expedia
Frigate's Nest in Little Torch
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Welcome to your exclusive waterfront retreat in the enchanting Little Torch Key, nestled in the heart of the Florida Key ...
From $2234 per night (USD)
Expedia
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VRBO
You’re on island time at “The Island Girl”.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come out an relax at our tropical escape. Only 33 miles North of Key West and 7 miles south of Bahia Honda State Park. O ...
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VRBO
From $257 per night (USD)
Expedia
🐠 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)
Expedia
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 $349 per night (USD)
Expedia
FISHERMANS DREAM HOUSE
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bring your boats to this amazing house with 180ft. of seawall secluded on a corner lot. Boat ramp minutes away. Ice make ...
From $349 per night (USD)
Expedia
From $427 per night (USD)
VRBO
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)
VRBO
From $838 per night (USD)
Expedia
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)
Expedia
From $407 per night (USD)
VRBO
Enjoy sunrises at this cozy canal front home !
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
GRAND SLAM 1952 Coral Way, Big Pine Key Welcome to the Grand Slam! This Unique rental will make y ...
From $407 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $160 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Sunset Hideaway, Pool home on canal
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located at the end of the road on the Gulf side of Big Pine Key and one in from open water this spacious 3 bedroom 3 bat ...
From $361 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 $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 $464 per night (USD)
VRBO
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)
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
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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
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Expedia
Big Pine Key Home on Bogie Channel w/ Dock & Slip!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Inspired by the Bogie Channel right outside, this Big Pine Key vacation rental is the perfect setting for nonstop advent ...
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Expedia
From $361 per night (USD)
VRBO
Hammock Bay! Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unique private compound offers 200ft extravagant dock that can hold up to a 50ft vessel and provides safe harbor for any ...
From $361 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Keys 3 Bedroom Corner Home near Beach & Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spacious very private home only 3 miles from beach and 25 miles from Key West. Home is only 1 mile from boat ramp and cl ...
From $611 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Very Private 3 Bedroom / 2 Bath Canal Home in Little Torch Key w/ Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Paradise Blue....a true slice of paradise on Little Torch Key! This private retreat sits on 2 lots with the h ...
From $424 per night (USD)
VRBO
From $234 per night (USD)
Expedia
La Brisa: Discover Paradise, Exquisite Canal Front Home on Little Torch Key, Dockage & Dog-Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $234 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Ocean Front Living in the Florida Keys, on beautiful Big Pine Key.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This open water house sits on the shore of Big Spanish Harbor and is only a boat ride away from the best fishing and div ...
From $328 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 $256 per night (USD)
VRBO
Peaceful Big Pine Tropical Seaside
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to newly built Seaside Ocean Escape—a beautiful 3BR coastal retreat boasting a 75-ft dock with quick direct ocea ...
From $256 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Lost At Atlantis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The perfect vacation home in Big Pine Key. This beautiful 3 bedroom, 2 bath canal front home has over 100' concrete sea ...
From $273 per night (USD)
VRBO
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 $423 per night (USD)
VRBO
Hellenga Haven | Amazing 3 bed/3 bath waterfront retreat with pool & dockage on Big Pine Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Indulge in the ultimate escape at this secluded monthly vacation rental on Big Pine Key. Nestled in serenity, this hidde ...
From $423 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Mi Sueno | 3 bed, 2 bath canalfront home with new pool & spa!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the laid-back island lifestyle in this delightful ground-level pool home located in a quiet neighborhood on t ...
From $345 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Relax in Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very eclectic Conch-style Key West home on Big Pine Key. Appropriately appointed for a relaxing stay. Large living room ...
From $218 per night (USD)
VRBO
From $4285 per night (USD)
VRBO
Beach house BPK
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach house close to the water, close to beaches, boat ramps, parks, restaurants, shopping, flea market, stores, Bahia H ...
From $4285 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
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VRBO
Florida keys House for Rent is a Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The most beautiful Island , “”Our paradise in Little torch key”” ,Open Canal at the back yard only 5 minutes on Boat Rid ...
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VRBO
From $249 per night (USD)
Expedia
JULY/AUG 2025 STILL AVAILABLE!!! 3 BR Canal Home in Big Pine - Private Pool/Spa!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Barracuda Bungalow in Big Pine Key! This quaint ground level home is reminiscent of old Florida Keys with som ...
From $249 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Big Pine Key House 4/2 with 75’ dock and a stunning bay view.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
2 stories house with 4 bedrooms and 2 full bathrooms. All amenities included. A 75’ dock and a terrace to a beautiful su ...
From $210 per night (USD)
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 $276 per night (USD)
VRBO
Cloud Nine Casita At Big Pine
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
About this space Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront property featuring modern fini ...
From $276 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Big Pine House, 4/2 two story, canal access 75 ft dock and stunning Bay view.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
House for rent in paradise. Bring your family and enjoy great fishing, beautiful sunsets from the balcony and just relax ...
From $250 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Sunrise Oasis in big pine key
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Nestled in the tranquil surroundings of Big Pine Key, Sunrise Oasis offers a serene retreat for those seeking a peaceful ...
From $517 per night (USD)
VRBO
From $317 per night (USD)
Expedia
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)
Expedia
From $219 per night (USD)
VRBO
Cozy house on peaceful Little Torch Key with majestic view of Big Pine Channel!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Little Torch Key is waiting for you at this 2-bedroom house. This beautiful property features 2 queen beds and a queen p ...
From $219 per night (USD)
VRBO
From $147 per night (USD)
VRBO
Charming canal front 2-bedroom home with WiFi and AC in Little Torch Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRBO required we create a new listing after 9 years and 20 perfect 5 star ratings!!! We had the same guests for the pas ...
From $147 per night (USD)
VRBO
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 $175 per night (USD)
Expedia
Captain & Mermaid's Diamond #BP25
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Seafront Tropical Retreat – Big Pine Key Getaway Escape to this serene waterfront oasis in Big Pine Key, just 30 miles f ...
From $175 per night (USD)
Expedia
From $289 per night (USD)
VRBO
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)
VRBO
From $210 per night (USD)
Expedia
OPEN FOR 2025 LOBSTER SEASON! Nice 2-bedroom Canal Home in serene Big Pine Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Big Pine Breeze! This charming 2 bedroom/2 bathroom home is located just one canal from open water making it ...
From $210 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Open Water Modern Home 2/2
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RARE FIND OPEN WATER VIEWS FROM ALL ANGLES AND DECK! Located on Little Torch Key 28.5 mm Jolly Roger Estates. Meticulous ...
From $433 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Beautiful 3 Bedroom Canal Home in Little Torch Key, FL w/ Great Boating Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to "SUNSET LANDING". Located in one of the best boating areas in the Florida Keys, this beautiful 3 bedroom home ...
From $415 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 $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 $398 per night (USD)
VRBO
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
County zoning regulations require a minimum rental period of 28 nights, and no exceptions can be made. Please review add ...
From $398 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 $277 per night (USD)
VRBO
Hibiscus House - Heated Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Located in Big Pine Key, 30 min. drive to Key West or Marathon. Bahia Honda beach 15 min. This newly renovated4 Bedroom ...
From $277 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Star Room Barnacle Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This b ...
From $358 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Ocean Depth Room Barnacle Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort and adventure combine seamlessly. This ...
From $545 per night (USD)
VRBO
From $596 per night (USD)
Expedia
Treehouse Private Village Barnacle Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This b ...
From $596 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Ocean View Suite Barnacle Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort and adventure combine seamlessly. This ...
From $506 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Beach View Room Dormitory Room Barnacle Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort and adventure combine seamlessly. This ...
From $487 per night (USD)
Expedia
From $318 per night (USD)
VRBO
La Tortuga: Amazing 2BR Canal Front Home on Big Pine Key, Private Pool, Spa, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $318 per night (USD)
VRBO
From $440 per night (USD)
Expedia
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)
Expedia
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 $346 per night (USD)
VRBO
The Tree-House: Tropical getaway in a lush private jungle property!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Nestled in the woods of Little Torch Key, this exquisite tree-house style cottage offers complete privacy from the outsi ...
From $346 per night (USD)
VRBO
From $304 per night (USD)
VRBO
2 BR / 2 BA Canal Home in Little Torch Key - Big Boat Access and Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Calypso Corner! This tropical Keys home that sleeps 6 has a spacious dock and patio area, a fully equipped ki ...
From $304 per night (USD)
VRBO
From $155 per night (USD)
VRBO
Cozy 2-bedroom house in charming Little Torch Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the beauty of Little Torch Key from this beautiful 2-bedroom house. With 1 queen bed and 2 full beds, guests ca ...
From $155 per night (USD)
VRBO
From $227 per night (USD)
VRBO
Angler's Oasis w/ Boat Dock in Big Pine Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Canal View | Bait Freezer & Fish Cleaning Station | Trailer Parking Available Make the most of your next extended stay ...
From $227 per night (USD)
VRBO
From $210 per night (USD)
Expedia
🌴 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 $210 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Keys Breeze | 2 bedroom, 2 bathroom canalfront home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the ultimate Lower Keys retreat at our brand-new, 2-bedroom, 2-bathroom vacation rental on a serene canal in be ...
From $283 per night (USD)
VRBO
From $202 per night (USD)
Expedia
🌴 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)
Expedia
From $261 per night (USD)
VRBO
Sea-Esta: 3BR Canal-Front Escape on Big Pine Key, Pool, Dockage & Quick Access to Gulf & Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $261 per night (USD)
VRBO
From $483 per night (USD)
Expedia
A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wild Deer Heaven – A Serene Florida Escape in the Heart of the Keys Nestled in the heart of the Florida Keys, Wild Deer ...
From $483 per night (USD)
Expedia

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Results: 234 Rentals