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 $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
$Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D$
From $225 per night (USD)
Expedia
Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $225 per night (USD)
Expedia
From $232 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 $232 per night (USD)
VRBO
$Bay View 2 Bed \/ 2.5 Bath Vacation Townhome Rental in Key West Area$
From $478 per night (USD)
Expedia
Bay View 2 Bed \/ 2.5 Bath Vacation Townhome Rental in Key West Area
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Little Torch Cottages is the perfect Keys vacation get away. Our luxury inspired 2 bedroom townhomes with bay / ocean vi ...
From $478 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Direct Oceanfront Cottage-Sunrise View- #2,
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer and public ramp just arou ...
From $211 per night (USD)
VRBO
From $104 per night (USD)
Expedia
Peaceful Island Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This studio bedroom has a private entrance with rustic island feel. It is sufficient for ONE person, only. Queen- size b ...
From $104 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Waterfront Big Pine Key Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
House, 2 Bedrooms + Sofa bed, 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the ...
From $180 per night (USD)
VRBO
Click For Pricing
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. ...
Click For Pricing
Expedia
From $639 per night (USD)
VRBO
Manatee Watch | Gorgeous pool, 5 bedrooms, easy ocean access on Big Pine Key
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offer ...
From $639 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the chann ...
From $193 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Lower Keys Retreat.....
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful home located in Eden Pines subdivision on Big Pine Key has the best of everything. Furnished with the fin ...
From $284 per night (USD)
VRBO
From $216 per night (USD)
Expedia
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)
Expedia
From $265 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 $265 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cozy, clean, canal front home is located in a quiet, family friendly, National Key Deer Refuge. 3 bedroom, 2 baths ...
From $160 per night (USD)
Expedia
Click For Pricing
VRBO
Pirates Pleasure Fishing and Snorkeling.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property ...
Click For Pricing
VRBO
From $322 per night (USD)
Expedia
5 Pirate's - Pool & seawall for boat
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
3 bedroom/2 bath - Canal Front Home on Little Torch Key with; heated pool, concrete seawall and tiki hut. There is an o ...
From $322 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Waterfront Big Pine Key Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
House, 2 Bedrooms + Sofa bed, 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the ...
From $180 per night (USD)
VRBO
$2\/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!$
From $154 per night (USD)
Expedia
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 $154 per night (USD)
Expedia
$Your Best Fishing And Relaxing Experience! 2\/2 Waterfront Home$
From $212 per night (USD)
VRBO
Your Best Fishing And Relaxing Experience! 2\/2 Waterfront Home
Bedrooms:
3
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 $212 per night (USD)
VRBO
$Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW$
From $375 per night (USD)
Expedia
Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW
Bedrooms:
3
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 $375 per night (USD)
Expedia
From $775 per night (USD)
VRBO
Oceanfront Paradise w Dock for your 35' boat and 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 ice maker, 50" TV, refridgerator, fire p ...
From $775 per night (USD)
VRBO
From $237 per night (USD)
Expedia
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
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 $237 per night (USD)
Expedia
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 $379 per night (USD)
Expedia
FLORIDA KEYS PARADISE! HEATED SWIMMING POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
For Lazy Days is a beautiful 3 bedroom 2 bathroom house on a quiet street. (king in master, king in 2nd room, queen & fu ...
From $379 per night (USD)
Expedia
$Luxury Ocean View 2 Bed \/ 2.5 Bath Townhome in the Keys$
From $499 per night (USD)
VRBO
Luxury Ocean View 2 Bed \/ 2.5 Bath Townhome in the Keys
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bedroom townhomes off ...
From $499 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Waterfront Home in The Fabulous Florida Keys with Peak-A-Boo Views of the Bay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
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 ...
From $210 per night (USD)
Expedia
From $149 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 $149 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Conch House on a Quiet Canal : Monthly Only
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical ...
From $205 per night (USD)
Expedia
From $230 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 $230 per night (USD)
VRBO
$HEAVENLY PARADISE-60' DOCK SO CLOSE TO OPEN WATER---\nLITTLE TORCH KEY$
From $176 per night (USD)
Expedia
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 $176 per night (USD)
Expedia
$BEAUTIFUL GETAWAY - DAZZLING SUNSETS-\nBIG PINE KEY-60' DOCK 5 MINUTES TO CHANNEL$
From $161 per night (USD)
VRBO
BEAUTIFUL GETAWAY - DAZZLING SUNSETS-\nBIG 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 $161 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Open water views, New heated & chilled pool. Huge master suite! wraparound decks
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $343 per night (USD)
Expedia
From $314 per night (USD)
VRBO
7 Seas Bring your boat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 bedroom/3 bath Canal Front Home on Little Torch Key with concrete seawall for docking your boat, sparkling pool and b ...
From $314 per night (USD)
VRBO
From $495 per night (USD)
Expedia
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
Bedrooms:
3
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 $495 per night (USD)
Expedia
$Connecting 2 Bed \/ 2.5 Bath Luxry Townhomes w\/Seperate Entrances - Can Sleep 12$
From $1104 per night (USD)
VRBO
Connecting 2 Bed \/ 2.5 Bath Luxry Townhomes w\/Seperate Entrances - Can Sleep 12
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Our luxury inspired water front resort community is the perfect Keys vacation get away. We offer connecting fully furnis ...
From $1104 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Beautiful Canal Front Heated Pool 4 Bdr Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Large heated / chilled swimming pool with tanning le ...
From $261 per night (USD)
Expedia
From $942 per night (USD)
VRBO
Waterfront Anchor House with Boat Basin & Ramp!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The ...
From $942 per night (USD)
VRBO
From $710 per night (USD)
Expedia
Waterfront Haven House with Boat Basin & Ramp!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The ...
From $710 per night (USD)
Expedia
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 $484 per night (USD)
Expedia
Luxury and Lovely Water Front House
Bedrooms:
2
Bathrooms:
3
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 $484 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Deep Water Corner Canal Lot with Heated Pool, Tiki Hut & 240' Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located on a large corner lot on beautiful Little Torch Key, this newly renovated, tropically-themed, three bedroom, two ...
From $349 per night (USD)
VRBO
From $431 per night (USD)
Expedia
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 $431 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Bungalow oasis with lots of room
Bedrooms:
2
Bathrooms:
3
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 $178 per night (USD)
VRBO
From $462 per night (USD)
Expedia
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)
Expedia
From $279 per night (USD)
VRBO
Paradise in the lower KEYS!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Master bedroom has a KING bed, second bedroom has a KING bed, third bedroom has a Queen and a full bed that sleep 3, ho ...
From $279 per night (USD)
VRBO
From $575 per night (USD)
Expedia
SEA FOREVER! Gorgeous Ocean-Front Paradise!
Bedrooms:
4
Bathrooms:
6
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)
Expedia
From $139 per night (USD)
VRBO
Little Torch Tropical Oasis April Available
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LITTLE TORCH TROPICAL OASIS This Beautiful Oasis is a recently renovated Manufactured Home on the corner of 2 Crystal C ...
From $139 per night (USD)
VRBO
From $399 per night (USD)
Expedia
ISLAND TIME PARADISE HOUSE!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Enjoy breathtaking views of ISLAND TIME PARADISE (our nickname) in Big Pine Key. Its our spacious 3 bedroom 2 bathroom ...
From $399 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Escape to Eden | Canalfront half-duplex with short run to channel on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean spac ...
From $171 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Canal Front Home in Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in ...
From $234 per night (USD)
Expedia
From $289 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 $289 per night (USD)
VRBO
From $2805 per night (USD)
Expedia
A Tropical Luxury Getaway, Your own private resort!!
Bedrooms:
7
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 $2805 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Beautiful, newly redone home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Canalside ...
From $263 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Pool house with open water and sunset in the Florida Keys
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom 2 bath house on Big Pine Key. Property includes 70' dock with boat lift, double lot, heated swimming pool, f ...
From $570 per night (USD)
VRBO
From $1045 per night (USD)
VRBO
Fishermen`s Paradise | Waterfront home with huge pool, 220-foot dock & gorgeous interior
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your perfect island retreat! This freshly remodeled three-bedroom, four-bathroom vacation home on Big Pine of ...
From $1045 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Amazing Pool & Canal Ground Level Home, Ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. (POOL HEAT AV ...
From $402 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Cedar Cottage | Adorable canalfront cottage, lots of dockage on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your perfect slice of paradise in the heart of the Florida Keys! This newly remodeled 2 bed/2 bath home on a ...
From $219 per night (USD)
VRBO
From $486 per night (USD)
Expedia
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. BRAND NE ...
From $486 per night (USD)
Expedia
$New listing 3bd\/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $247 per night (USD)
VRBO
New listing 3bd\/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a 3 Bedroom/2 Bath cana ...
From $247 per night (USD)
VRBO
From $1779 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 $1779 per night (USD)
Expedia
From $493 per night (USD)
VRBO
2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our cozy 2 bedroom 2 bath 2 story home with a private pool offers a vacation to remember in the Lower Keys. Located in L ...
From $493 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Ocean views from every room. This peaceful and gorgeous property has a NEW DOCK!
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 $238 per night (USD)
Expedia
From $642 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 $642 per night (USD)
VRBO
From $377 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 $377 per night (USD)
Expedia
From $489 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 $489 per night (USD)
VRBO
From $555 per night (USD)
Expedia
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 $555 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
$New Construction Private Luxury Waterfront Home w\/ Heated Pool$
From $468 per night (USD)
Expedia
New Construction Private Luxury Waterfront Home w\/ Heated Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
New construction 4 bedroom waterfront home on a double lot with heated pool, floating dock, tiki bar, deep canal with qu ...
From $468 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
Bedrooms:
2
Bathrooms:
4
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 $294 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 $295 per night (USD)
VRBO
Welcome to Casa Del Mar 305 5251254
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Welcome to "Casa Del Mar" (305) 5251254. a 3/2 brand new mid-century modern home in Paradise! This home is a monthly v ...
From $295 per night (USD)
VRBO
$Waterfront home with boat dock, 2 kayaks, 2 bikes, AC & W\/D - dog-friendly$
From $336 per night (USD)
Expedia
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 $336 per night (USD)
Expedia
$DREAMS COME TRUE - 75' DOCK - 250 ' TO OPEN CHANNEL\nBIG PINE KEY FL$
From $161 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 $161 per night (USD)
VRBO
From $221 per night (USD)
Expedia
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 $221 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $228 per night (USD)
Expedia
Perfect getaway keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite coun ...
From $228 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Big Pine Latitude Adjustment | 5 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Location location location! Room for the whole family in this gorgeous 5 bedroom 3 bath pool home on Big Pine Key. Home ...
From $439 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Newly Remodeled Corner House on the Water
Bedrooms:
2
Bathrooms:
3
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 $180 per night (USD)
Expedia
From $492 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 $492 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Big Pine Key Paradise Canal front fenced yard.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WINTER 2025 OPEN Canal front fenced in home w/dock, boat ocean access, hot tub. 28 Night Min Stay, WiFi Full kitchen F ...
From $215 per night (USD)
Expedia
From $254 per night (USD)
VRBO
New Beach House-Boat & Dog Friendly 30 mins Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Brand new! Pet friendly, quiet and clean beach house. Located on Big Pine Key. Only minutes from boat ramps, white sand ...
From $254 per night (USD)
VRBO
From $497 per night (USD)
Expedia
Water View Town Home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bd townhomes offer br ...
From $497 per night (USD)
Expedia
From $497 per night (USD)
VRBO
Water View Town home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bd townhomes offer br ...
From $497 per night (USD)
VRBO
Click For Pricing
Expedia
Easy access to the Ocean and Gulf
Bedrooms:
3
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 ...
Click For Pricing
Expedia
From $184 per night (USD)
VRBO
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 $184 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Canal Front Pool Home ( BPL 2070 )
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 bedroom 2 bath home offers so many special features all in the perfect location. Situated around the corner from ...
From $316 per night (USD)
Expedia
$Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic\/Gulf Waters$
From $191 per night (USD)
VRBO
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic\/Gulf Waters
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $191 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $180 per night (USD)
Expedia
From $865 per night (USD)
VRBO
Conch House - Ocean front with dock and pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Conch House is located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard! ...
From $865 per night (USD)
VRBO
From $124 per night (USD)
Expedia
FALL SPECIAL!!! NEW RATES<br>🏴‍☠️ PIRATES PLEASURE 🏴‍☠️<br>
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Pirates Pleasure is a family owned home in a small neighborhoood community on the bay side of our hidden gem...Little To ...
From $124 per night (USD)
Expedia
From $846 per night (USD)
VRBO
Little Torch Key Nest - Ocean view with pool
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitch ...
From $846 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Modern multi story waterfront home, 30 minutes from Key west.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
One of a kind custom modern home, brand new all concrete construction. Multi level exclusive residence. 3 floors of livi ...
From $545 per night (USD)
Expedia
From $217 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 $217 per night (USD)
VRBO
$OCEAN FRONT PARADISE\/290 ft PRIVATE DOCK\/AWESOME VIEWS$
From $782 per night (USD)
Expedia
OCEAN FRONT PARADISE\/290 ft PRIVATE DOCK\/AWESOME VIEWS
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
GREAT SNORKELING UNDER DOCK. FISH FROM DOCK TOO. OUR PICTURES OF THE HOUSE ARE AFTER IRMA OUR DOCK SURVIVED WITHOUT A S ...
From $782 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Lovely Canal Front Big Pine Key House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canal front house in a quit peaceful neighborhood. South of Marathon <20-30 min> and North of Key West <40 min aprox. U ...
From $288 per night (USD)
VRBO
From $495 per night (USD)
Expedia
2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Little Torch Cottages offers the perfect Keys location, fully appointed luxury 2 bedroom 2.5 bath townhome with breath t ...
From $495 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Starfish - Ocean front with dock and pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Starfish House - Dock your boat at your back door 3 bedroom 2 bath ocean front home with pool This home is a GEM. Very ...
From $670 per night (USD)
VRBO
$Beautiful 2\/2 Waterfront Designer Home for your family vacation$
From $155 per night (USD)
Expedia
Beautiful 2\/2 Waterfront Designer Home for your family vacation
Bedrooms:
2
Bathrooms:
3
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 $155 per night (USD)
Expedia
From $197 per night (USD)
VRBO
Ocean Front Access - just 30 miles to Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer, public ramp just around ...
From $197 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Awesome Open Water View at Blue Heron Estate
Bedrooms:
5
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 $852 per night (USD)
Expedia

Search Your Destination Now!

Big Pine Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 234 Rentals