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 $718 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' long dock, pool, spectacular views of distant island ...
From $718 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Manatee Watch | 5 bedrooms, pool, ocean access
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key The Space: Discove ...
From $500 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Tarpon Tales | Fantastic boating, pet-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Boater’s Dream: Double Dockage, Quick Channel Access, Fenced Yard The Space: Welcome to your ideal Florida ...
From $212 per night (USD)
Expedia
From $369 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 $369 per night (USD)
VRBO
From $215 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 $215 per night (USD)
VRBO
From $309 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 $309 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy, clean, canal front home located in a quiet, family friendly, National Key Deer Refuge. 3 bedroom, 2 baths with sc ...
From $159 per night (USD)
VRBO
From $210 per night (USD)
VRBO
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in ...
From $210 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** Florida Keys, Big Pine Key, located in Big Pine Key Florid ...
From $314 per night (USD)
Expedia
From $588 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 $588 per night (USD)
VRBO
$\Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\$
From $288 per night (USD)
Expedia
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $288 per night (USD)
Expedia
From $567 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 $567 per night (USD)
VRBO
From $197 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 $197 per night (USD)
VRBO
From $289 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 $289 per night (USD)
VRBO
From $172 per night (USD)
VRBO
DAZZLING SUNSETS-80FT WIDE CANAL BIG PINE KEY-60' DOCK 5 MINUTES TO CHANNEL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
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 ...
From $172 per night (USD)
VRBO
From $486 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 $486 per night (USD)
VRBO
From $270 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 $270 per night (USD)
Expedia
From $409 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 $409 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Bungalow oasis with lots of room
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fenced property! Not to mention all the key deer that come and visit. 2 bedrooms 1.5 bathroom 1 car garage concrete ho ...
From $165 per night (USD)
Expedia
From $502 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 $502 per night (USD)
VRBO
From $630 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 $630 per night (USD)
VRBO
From $321 per night (USD)
VRBO
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 $321 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Pool house with open water and sunset in the Florida Keys
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 bedroom 3 bath house on Big Pine Key. Property includes 70' dock, double lot, heated swimming pool, fire pit, BBQ, i ...
From $633 per night (USD)
VRBO
From $1039 per night (USD)
VRBO
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Summary: Welcome to Fishermen's Paradise, a beautifully appointed open-water retreat on Big Pine Key. Enjoy a private h ...
From $1039 per night (USD)
VRBO
From $397 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 $397 per night (USD)
Expedia
From $440 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 $440 per night (USD)
VRBO
$New listing 3bd/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $273 per night (USD)
Expedia
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 $273 per night (USD)
Expedia
Click For Pricing
VRBO
Big Pine - Bring your boat! - 4BR/3BA ocean front, private pool & dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Tiki Beach House is a 4 bedroom, 3 bath house, located on the Gulf side of the island of Big Pine Key. Over an acre an ...
Click For Pricing
VRBO
From $575 per night (USD)
VRBO
Private water front property with ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Beautiful 15,000 sq ft water front property. Steps away from the famous No Name Pub. Steps away from the no name bridg ...
From $575 per night (USD)
VRBO
From $323 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 $323 per night (USD)
VRBO
From $192 per night (USD)
VRBO
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 $192 per night (USD)
VRBO
From $164 per night (USD)
VRBO
BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL BIG 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 $164 per night (USD)
VRBO
From $248 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 $248 per night (USD)
VRBO
From $253 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 $253 per night (USD)
VRBO
Click For Pricing
VRBO
Big Pine Latitude Adjustment
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: Welcome to Big Pine Latitude Adjustment, a beautifully remodeled 5-bedroom, 3-bath waterfront retreat for up t ...
Click For Pricing
VRBO
From $219 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 $219 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Beautiful Family Big Pine Retreat! Short drive to Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Big Pine Key offers the most peace & tranquility of the FL Keys! This home offers plenty of space and parking along side ...
From $514 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Big Pine Getaway - Pets + Boats Welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience modern coastal luxury in this brand-new Big Pine Key home. Just minutes from Bahia Honda’s white-sand beaches ...
From $249 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Secluded Hideaway with private pool and canal
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home is tastefully decorated with a tropical feel. There is a Flat screen TV, high speed internet, central air, an ...
From $197 per night (USD)
Expedia
From $145 per night (USD)
VRBO
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 $145 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Bedrooms:
2
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 $151 per night (USD)
Expedia
From $381 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 $381 per night (USD)
VRBO
From $375 per night (USD)
VRBO
Canal-Front Keys Retreat / Jacuzzi • Sleeps 14
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Welcome to your relaxing Florida Keys getaway — a spacious canal-front retreat designed for comfort, connection, fishin ...
From $375 per night (USD)
VRBO
From $966 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 $966 per night (USD)
VRBO
From $263 per night (USD)
VRBO
Casa Blanca | Georgeous home on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Gorgeous ground-level 2 bed/2 bath home on Big Pine Key The Space: Escape to your own piece of paradise wi ...
From $263 per night (USD)
VRBO
From $231 per night (USD)
VRBO
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 $231 per night (USD)
VRBO
From $207 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 $207 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Big Pine Key, 75 feet wide canal 8 feet depth with Direct Access Gulf & Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
DO NOT BOOK STAYS THAT BOOK INTO 2 MONTHS WITHOUT APPROVAL (example: 7/15-8/15). This property is only allowed monthly r ...
From $345 per night (USD)
VRBO
From $252 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 $252 per night (USD)
VRBO
From $1188 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 t ...
From $1188 per night (USD)
VRBO
From $352 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 $352 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Slice of Paradise: Big Pine Key Waterfront | Heated Pool, Dockage & Open-Water Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
SLICE OF PARADISE – OPEN-WATER LIVING ON BIG PINE KEY County zoning requires a minimum rental period of 28 nights, ...
From $345 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $171 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 $171 per night (USD)
VRBO
From $498 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 $498 per night (USD)
Expedia
From $381 per night (USD)
VRBO
LARGE LOT & RV 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 $381 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Reel Paradise | Boating & fabulous sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Fabulous sunsets from this canalfront retreat on Big Pine Key The Space: Cozy 2 bed/2 bath canalfront mont ...
From $211 per night (USD)
Expedia
From $427 per night (USD)
VRBO
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 $427 per night (USD)
VRBO
From $273 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 vacatio ...
From $273 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Yellowstone by the Sea
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Here is a unique and tranquil getaway that is the best of all worlds. Enjoy setting in the soft tropical breezes that ov ...
From $267 per night (USD)
VRBO
From $248 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 $248 per night (USD)
Expedia
From $266 per night (USD)
VRBO
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 $266 per night (USD)
VRBO
From $470 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 $470 per night (USD)
Expedia
From $247 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 $247 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Boater’s Paradise: 3BR Canal Front Home + Fish Cleaning Station
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our charming Florida Keys bungalow, a 3-bedroom, 2-bathroom retreat that comfortably accommodates up to 8 gue ...
From $271 per night (USD)
Expedia
From $307 per night (USD)
VRBO
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 $307 per night (USD)
VRBO
From $197 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 $197 per night (USD)
Expedia
From $392 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 $392 per night (USD)
VRBO
From $161 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 $161 per night (USD)
Expedia
From $309 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 $309 per night (USD)
VRBO
From $648 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 $648 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Blue Coral Lagoon Pool Seaside
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently built a few years ago features a new patio & adding a heated pool by Oct ? It blends upscale finishes with a fr ...
From $407 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $504 per night (USD)
VRBO
Hellenga Haven | Waterfront pool home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Amazing 3 bed/3 bath waterfront retreat with pool & dockage on Big Pine Key The Space: Indulge in the ulti ...
From $504 per night (USD)
VRBO
From $215 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 $215 per night (USD)
VRBO
From $995 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 $995 per night (USD)
VRBO
From $307 per night (USD)
Expedia
3 BR Canal Home in Big Pine Key, FL - Private Pool/Spa - Great Boating Access!!!
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 $307 per night (USD)
Expedia
From $448 per night (USD)
VRBO
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 $448 per night (USD)
VRBO
From $154 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 $154 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Charming 2-bedroom 2- bath home located in the middle of The Key Deer Refuge.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
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 $420 per night (USD)
VRBO
From $358 per night (USD)
Expedia
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 $358 per night (USD)
Expedia
From $246 per night (USD)
VRBO
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 $246 per night (USD)
VRBO
From $264 per night (USD)
Expedia
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 $264 per night (USD)
Expedia
From $321 per night (USD)
VRBO
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 $321 per night (USD)
VRBO
From $483 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 $483 per night (USD)
Expedia
From $446 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 $446 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Unwind in the Keys! Extended-Stay Big Pine Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Serene Screened Porch w/ Canal View | Bait Freezer & Fish Cleaning Station | Private Dock Make the most of your month i ...
From $171 per night (USD)
Expedia
From $343 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 $343 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Sea-Esta | Heated Pool • 75' Dock • Deep Water Canal • Boater's Paradise on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
28-Night Minimum Stay Required County zoning regulations require a minimum rental period of 28 nights. No exception ...
From $246 per night (USD)
Expedia
From $187 per night (USD)
VRBO
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 $187 per night (USD)
VRBO
From $562 per night (USD)
VRBO
Yeya's Hideaway | 4 bedrooms, fabulous views
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Luxury 4 bedroom canalfront rental with fantastic outdoor living. Pool coming soon! The Space: Welcome to ...
From $562 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Charming canal front 2-bedroom house with WiFi, AC in fantastic Big Pine Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this delightful house in picturesque Big Pine Key. With 2 queen beds in 2 cozy bedrooms, a modern bathroom wit ...
From $230 per night (USD)
VRBO
From $446 per night (USD)
Expedia
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 $446 per night (USD)
Expedia
From $824 per night (USD)
VRBO
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
This spacious house in Big Pine Key offers 3 cozy bedrooms - 2 with king beds, 1 with 2 bunk beds with 2 full beds on bo ...
From $824 per night (USD)
VRBO
From $385 per night (USD)
Expedia
3-bedroom waterfront. Cable-WiFi, AC, Hot tub, Dock. Book for Winter 2026-27 !!
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 $385 per night (USD)
Expedia
From $285 per night (USD)
VRBO
NEWLY RENOVATED 3/2 WITH POOL AND CANAL ACCESS! Pet-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Minimum 28 day rental period. Please feel free to reach out for more information. Escape to a world of tranquility and i ...
From $285 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unwind in Big Pine Key at this brilliant house. With 2 cozy bedrooms featuring a king and queen bed, guests can relax in ...
From $445 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Airstream Travel Trailer
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Settle in and enjoy a comfortable stay in this 1-bedroom, 1-bath trailer. The bedroom includes a full-size bed, plus a f ...
From $249 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Airstream Travel Trailer
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Settle in and enjoy a comfortable stay in this 1-bedroom, 1-bath trailer. The bedroom includes a full-size bed, plus a f ...
From $252 per night (USD)
Expedia

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Results: 122 Rentals