
Beachfront vacation rentals in Big Pine Key
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Big Pine Key
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

RV In The Keys | Tropical Retreat
Tropical retreat in the heart of Florida Keys. Relax in this fully furnished private & clean RV with parking just 30 miles from Key West. Enjoy breezy indoor/outdoor living with a fold-down patio, 2 TVs, full kitchen, bathroom, pantry. Outside seating g with awning. Nestled in a local RV park w/ pool, fish station, and coin laundry. Vacation here & swim in the ocean —Next to Pine Channel in Big Pine Key and 10 miles to Bahai Honda State Park. Walk to groceries, Walgreens, restaurants. Staycation

*NEW* Private Beach, pool & fully loaded kitchen
Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Palm - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

Oceanside home 111, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Island Breeze
Key Colony Beach is walking distance to some of the very best restaurants, harbor, parks, & aquarium but best of all is located on one of the rare private white sandy beaches in the Keys. Enjoy the beautiful sunrise and sunsets without leaving your unit. 2+2 both ensuite, fully furnished, kitchen gourmet ready with plenty of counter space. Washer & dryer, under cover 2 car parking, elevator, pool and more. Book your stay today. POOL is open. 7 day minimum City requirement.

SeaEsta! Bring your boat & 1 block to the beach!
Take a 1 Block walk to Sombrero Beach, dock your boat at this waterfront home or simply relax on the patio. 3 Bedrooms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar. Our home is fully furnished with all the essentials. We even include Kayaks, Bikes and Fishing Poles as well as Corn Hole and Giant Jenga. Boat Rental is offered at an additional cost. - VR License No: VACA -20-147

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #10 offers one king bed, a fully equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys sunset.
Popular amenities for Big Pine Key beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

Charming Beach House directly ON the beach

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Key West Luxury Houseboat at Yacht Club Resort
Beachfront home rentals with a pool

3BR Oceanfront with private pool & dock

Key West 2 BR Deluxe, Beach Front, sleeps: 6

Powell Family Resort

Stunning tropical Ocean view condo

Hyatt Windward Pointe Resort: Beachfront Condo

Oceanfront Key West Condo

Beachfront Condo on Coco Plum Beach w/heated pool

Florida Keys Getaway w/ Stunning Ocean Views
Private beachfront home rentals

Oceanfront Sunrise Condo Private Beach Heated Pool

Beachside Unit 14 - Brand New Kitchen and Bathroom

Oceanfront Breeze, Stunning Views, Beach/Pool

Paradise awaits.

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

A slice of paradise!

Coastal Key Colony Beach Condo, Oceanfront Complex

Steps to the Beach Condo - Key Colony Beach
Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at R3,208 ZAR per night before taxes and fees

Verified guest reviews
Over 230 verified reviews to help you choose

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




