
House holiday rentals in Big Pine Key
Find and book unique houses on Airbnb
Quick stats about house rentals in Big Pine Key

Total holiday rentals
Explore 170 holiday rentals in Big Pine Key

Nightly prices starting at
Big Pine Key holiday rentals start at $169 NZD per night before taxes and fees

Verified guest reviews
Over 1,360 verified reviews to help you choose

Family-friendly holiday rentals
160 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 90 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
170 of Big Pine Key holiday 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!
Top-rated house rentals in Big Pine Key
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

Keys Beach Retreat Close to Key West
Your family will be close to everything when you stay at this centrally-located place. we are only 3 miles from Bahia Honda Beach and about 27 Miles from Key West. We are perfect for nature lovers and adventure seekers. 1. National Key Deer Refuge: Home to the endangered Key deer, this refuge offers beautiful trails and great for wildlife viewing and 2.Looe Key Reef: A popular snorkeling and diving location, featuring vibrant coral reefs. 3.Sand bars nearby & world famous fishing spots.

Oceanfront new 360’ dock, tiki hut-dogs OK
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut, fire pit area, and beach with NEW 360' dock for any size boat and fishing!! You will not want to go inside, but when you do, you will find a very "Keysey" living space with plenty of water views. Only 9 miles from Bahia Honda State Park one of top 25 beaches in the US. We are also famous for key deer only found on Big Pine Key. They are friendly and everywhere. You can also walk to No Name Pub a famous eatery.

Oceanfront Cottage with 60’ Dock
Oceanviev Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON).

Hibiscus House
Located in Big Pine Key, 30 min. drive to Key West or Marathon. Bahia Honda beach 15 min. This newly renovated house is located next to National Key Deer refuge, enjoy the wild life from your porch. Heated / chilled saltwater pool nestled in back yard w/ tiki hut. Plenty of space for 10 guests. On site parking for 3 cars plus a boat trailer. Nearby boat ramp / boat rentals available. 1st and 2nd floor porches offer serene views w/ pleasant cool breezes. Come enjoy the Keys Life.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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***

Florida Keys Retreat
Apretreats home. Perfect for large boats or multiple watercrafts! Total 200 ft of dockage: 100ft of dock on the basin side! 18 ft deep! Another 100ft of dock on the canal side Large 5/4 home, where you can be together and have privacy at the same time Upstairs you have 3/2 2 king bedrooms 1 queen bedroom Downstairs you have 2 1/1 units, each with their own kitchenette, king bedroom Downstairs and futton/sleeper sofa Take a dip in the pool NOT PET FRIENDLY

Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Waterfront Anchor 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 Haven 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!

*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.

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
Popular amenities for Big Pine Key house rentals
House rentals with a pool

Oceanfront mermaid house pool and dock

Waterfront 2-bedroom Home w/Pool and Spa

Beach House, Private Pool, Dock, Gulf View Sunsets

Easy Ocean Access 30' Dock House Pool Cabana Club

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!

Amazing Oceanfront Home

P02 - 5 bed, 3.5 bath home with large private pool
Weekly house rentals

Relaxing Home in the Keys

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Oceanside home 111, dock,kayaks,bikes,pool,fishing

Boating Paradise Villa rental Lic# VACA-25-124

Fisherman's Paradise Cudjoe Key

Gorgeous Ocean View Home!

Oceanview Escape

Private Pool! Luxury Paradise Pointe, Pet Friendly
Private house rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

Florida Keys Oceanside Utopia

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Soothing Nest

Kingsail Resort Home

Flamingo Palms-April availability
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 | $497 NZD | $401 NZD | $418 NZD | $394 NZD | $381 NZD | $416 NZD | $460 NZD | $448 NZD | $394 NZD | $394 NZD | $387 NZD | $440 NZD |
| 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 |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Pet-friendly rentals Big Pine Key
- Rentals with a hot tub Big Pine Key
- Rentals with outdoor seating Big Pine Key
- Rentals with pools Big Pine Key
- Beachfront rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Villa rentals Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Waterfront rentals Big Pine Key
- Family-friendly rentals Big Pine Key
- Rentals with beach access Big Pine Key
- Condo rentals Big Pine Key
- Rentals with a fire pit Big Pine Key
- Apartment rentals Big Pine Key
- Rentals with a washing machine and dryer Big Pine Key
- Cottage rentals Big Pine Key
- Smoking-friendly rentals Big Pine Key
- Rentals with a kayak Big Pine Key
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Sea Oats Beach
- Bahia Honda State Park
- Conch Key
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Seven Mile Bridge
- Key West Lighthouse Museum
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- The Turtle Hospital
- Boyd's Key West Campground
- History Of Diving Museum
- Calusa Beach & Loggerhead Beach




