Beachfront holiday rental in Big Pine Key

Find and book unique beachfront homes on Airbnb

Top-rated beachfront accommodation in Big Pine Key

Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Superhost
A well-maintained 28-ft Grey Wolf RV is parked on a gravel lot, surrounded by tropical greenery. Two lounge chairs are positioned on a green patch of grass, creating a relaxing outdoor seating area. Sunshine filters through the clouds, adding a bright ambiance to the scene.
Tiny home in Big Pine Key
4.67 out of 5 average rating, 24 reviews

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

Top Guest favourite
An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.
Condo in Marathon
4.97 out of 5 average rating, 31 reviews

*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

Superhost
A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.
Condo in Duck Key
4.88 out of 5 average rating, 116 reviews

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.

Superhost
A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.
Home in Upper Sugarloaf Key
4.75 out of 5 average rating, 102 reviews

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.

Top Guest favourite
Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.
Home in Cudjoe Key
5 out of 5 average rating, 25 reviews

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.

Guest favourite
An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.
Condo in Summerland Key
5 out of 5 average rating, 18 reviews

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!

Superhost
A dining area features a round wooden table set with yellow placemats and white napkins. Light blue walls complement the soft furnishings, while large windows provide a view of tropical foliage and the outdoors. Natural light fills the space, enhancing the inviting atmosphere.
Home in Marathon
4.83 out of 5 average rating, 94 reviews

Waterfront Villa & Sunset Views

Come and relax on your own veranda that overlooks the turquoise waters of the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay local to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Superhost
A thatched-roof gazebo provides shade over a white picnic table, with sandy beach stretching towards the calm ocean. Sunlight reflects off the water, creating a bright atmosphere. Nearby, a few kayaks are visible on the shore, enhancing the beachside setting.
Condo in Marathon
4.73 out of 5 average rating, 15 reviews

Stylish Anglers Retreat Poolside and Ocean U16

Embrace the charm of the Keys in our serene escape for couples or families. Nestled just steps from a heated pool and the ocean, this marine-themed retreat offers king comfort, a cozy sofa sleeper, and a screened balcony for intimate evenings. Dive into local adventures with available beach gear, or unwind in our airy space, boasting a fully equipped kitchen and tasteful decor. Ideal for those seeking a blend of relaxation and oceanic exploration, it's your perfect coastal haven.

Superhost
An airy dining area features a white stone-topped table positioned beneath a stylish light fixture. Large glass doors allow natural light to flood the space, connecting indoor and outdoor seating areas. The wooden floor adds warmth to the contemporary design.
Home in Marathon
4.83 out of 5 average rating, 12 reviews

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

Guest favourite
The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.
Condo in Key Colony Beach
4.88 out of 5 average rating, 148 reviews

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.”

Superhost
A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.
Houseboat in Marathon
4.88 out of 5 average rating, 130 reviews

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.

Guest favourite
Home in Cudjoe Key
4.94 out of 5 average rating, 16 reviews

Blue Palms Retreat

This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.

Popular amenities for Big Pine Key beachfront rentals

Quick stats about beachfront rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key holiday rentals start at $272 AUD 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!

Destinations to explore