
House vacation rentals in Big Pine Key
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Top-rated house rentals in Big Pine Key
Guests agree: these houses are highly rated for location, cleanliness, and more.

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut
2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Cozy 2 br/2 bath home in Cudjoe
Discover a slice of Floridian paradise in our charming 2b/2bath located in Venture Out community, Cudjoe Key. Two bedrooms and an outdoor patio promise relaxation, while community amenities such as a pool, tennis courts, and kids' playground are available. A place to experience the laid-back Florida lifestyle and create unforgettable memories. Book your stay with us today and come live the dream in Cudjoe Key! ****Upon entry, there is a one-time community fee paid at the gate check-in: $125.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Dolphin Daydreams at Venture Out
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** DOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe

Salt&Seaglass. Key Colony. Screen Porch. Pool Club
This Key Colony Beach home is a welcoming, modern canal-front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large island and granite counter tops, a master bedroom with private bathroom and modern, plank flooring tile throughout the home. Enjoy the relaxing 9 X 20 ft porch & comfortable furniture. Outside: Lounge chairs & other seating, a kayak, a 37 foot dock

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
Popular amenities for Big Pine Key house rentals
House rentals with a pool

Grouper Getaway @ Ocean Isles Fishing Village

Florida Keys Retreat

Ocean~View*Pool*Dock*Kayaks*King Bed

COZY Family Home- 5 minutes from sombrero beach

Jan. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

Waterfront House with 37 ft Dock & Cabana Club

Boat Dock+King Bed & Cabana Club

Tropical Tides in Cudjoe Key 135
Weekly house rentals

Oceanfront Rooftop Views w/ 75ft of Dockage

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

New Listing Discount! Dockside Paradise

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

Chasing Sunrises | Family Style

2BR/2BA Retreat in the heart of Marathon! 3 beds

Roost Haven w/ free private parking spot

Gorgeous Ocean View Home!
Private house rentals

Updated Key Colony Tiki Hut-37.5 Dock-Cabana Club

Discount Available! Pool 100' Dock, Fun Amenities!

Secluded Waterfront home, Views, Dock, Amenities,

Waterfront Oasis w/Private Pool-Dockage-Beach

Yellowtail Getaway with Boat Dock and Pool 2

Island Breeze

Waterfront Oasis with Boat Dock & Pool!

Oceanview Escape
When is the best time to visit Big Pine Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,080 | ﺩ.ﺇ870 | ﺩ.ﺇ907 | ﺩ.ﺇ856 | ﺩ.ﺇ826 | ﺩ.ﺇ903 | ﺩ.ﺇ999 | ﺩ.ﺇ973 | ﺩ.ﺇ856 | ﺩ.ﺇ790 | ﺩ.ﺇ973 | ﺩ.ﺇ918 |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about house rentals in Big Pine Key

Total vacation rentals
Explore 170 vacation rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Family-friendly vacation rentals
160 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
170 of Big Pine Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Big Pine Key rentals

4.8 Average rating
Big Pine Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Conch Key
- Bahia Honda State Park
- Long Beach
- Florida Keys Aquarium Encounters
- Sunset Park
- Key West Butterfly & Nature Conservatory
- Fort Zachary Taylor Historic State Park
- Dolphin Research Center
- Seven Mile Bridge
- Southernmost Point
- Ernest Hemingway Home & Museum
- Key West Lighthouse Museum
- Robbies Marina Of Islamorada
- The Turtle Hospital
- Boyd's Key West Campground




