
House holiday 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.

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.

Tropical Paradise
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

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.

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.

Spacious 3Br/3Ba, 70ft Dock, March avail VACA23-16
Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor
Captain's Cove, your 4BR waterfront escape in Marathon, set on a quiet canal with direct ocean access. Designed for unforgettable Keys living for families and boaters alike. 🏊♂️ Private backyard pool ⛵ 30’ boat dock + 4 kayaks 🍳 Covered outdoor kitchen & BBQ 🚿 Spa-style rain & jet showers w/ luxury toiletries 🛏️ Ground-level comfort for 8 🐾 Pet & kid friendly
Popular amenities for house rentals in Big Pine Key
House rentals with a pool

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

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

Beach House, Private Pool, Dock, Gulf View Sunsets

Fisherman's Paradise Cudjoe Key

Waterfront Sanctuary in the Keys!

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

The Salty B Vacation Rental

Oceanfront Paradise with Kayaks & Paddleboards
Weekly house rentals

Relaxing Home in the Keys

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Oceanfront mermaid house pool and dock

Waterfront 2-bedroom Home w/Pool and Spa

Dolphin Daydreams at Venture Out

Tiki Time in Cudjoe Key 136

Marathon Paradise

Key Colony Second Wind
Private house rentals

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

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

Florida Keys Oceanside Utopia

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

Ocean Front Home in Great Location

Flamingo Palms-April availability

Boating Paradise Villa rental Lic# VACA-25-124

Casa Blue Flamingo
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 | $374 SGD | $302 SGD | $315 SGD | $297 SGD | $287 SGD | $313 SGD | $346 SGD | $337 SGD | $297 SGD | $297 SGD | $292 SGD | $331 SGD |
| 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 holiday rentals
Explore 170 holiday rentals in Big Pine Key

Nightly prices starting at
Big Pine Key holiday rentals start at $127 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
170 of Big Pine Key holiday rentals include wifi 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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- Rentals with beach access Big Pine Key
- Pet-friendly rentals Big Pine Key
- Flat rentals Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Waterfront rentals Big Pine Key
- Rentals with a firepit Big Pine Key
- Family-friendly rentals Big Pine Key
- Rentals with pools Big Pine Key
- Villa rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Beachfront rentals Big Pine Key
- Cottage rentals Big Pine Key
- Rentals with a hot tub Big Pine Key
- Apartment rentals Big Pine Key
- Rentals with a washing machine and dryer Big Pine Key
- Rentals with a kayak Big Pine Key
- Smoking-friendly rentals Big Pine Key
- Rentals with outdoor seating Big Pine Key
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Sea Oats Beach
- Conch Key
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Sunset Park
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Robbies Marina Of Islamorada
- Key West Lighthouse Museum
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Southernmost Point
- Boyd's Key West Campground
- History Of Diving Museum
- Calusa Beach & Loggerhead Beach




