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Beachfront vacation rentals in Big Pine Key

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Big Pine Key

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Top guest favorite

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

4.96 out of 5 average rating, 25 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

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, 109 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.

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

Condo in Key Colony Beach

4.91 out of 5 average rating, 193 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Top guest favorite

Home in Marathon

4.98 out of 5 average rating, 48 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

Home in Marathon

5 out of 5 average rating, 39 reviews

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

Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

A three-story oceanfront home is showcased, featuring a spacious outdoor deck and private pool area. Lush palm trees surround the property, and a sandy pathway leads to the entrance. The home is painted in a light color, blending with the bright blue sky.

Home in Cudjoe Key

4.91 out of 5 average rating, 11 reviews

Latitudes-Ocean Front Pool

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests.

Top guest favorite

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

4.93 out of 5 average rating, 356 reviews

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.

Top guest favorite

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

4.97 out of 5 average rating, 106 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

A beachside tiki hut provides shaded seating, surrounded by palm trees and white sandy shores. The clear blue ocean extends toward the horizon, reflecting sunlight. Lounge chairs are positioned nearby, inviting guests to relax in a tropical outdoor setting.

Condo in Key Colony Beach

4.89 out of 5 average rating, 156 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with 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.”

A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

Apartment in Marathon

4.87 out of 5 average rating, 54 reviews

Little Venice in Marathon (in the Beautiful Keys)

Little Venice in Marathon is a beautiful 2 bed / 2 bath fully remodeled waterfront home that offers the best Florida Keys Living. There are plenty of fun and adventurous activities to do just steps from your door. Including but not limited to boating, kayaking, biking, sport fishing and many more fun activities. Our home is equipped with everything you may possibly need to spend an enjoyable, relaxing vacation. Also this dream home has a 50 feet boat dock.

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

4.89 out of 5 average rating, 123 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.

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

Apartment in Marathon

4.97 out of 5 average rating, 107 reviews

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

Vacation rentals for every style

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Luxurious estates for the ultimate escape

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A space thats all yours, with room for everyone

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Quaint homes, peaceful surroundings

Popular amenities for Big Pine Key beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

A serene sunset view is captured from a wooden dock extending over calm waters. Silhouetted figures can be seen seated at the end of the dock, with vibrant orange and purple hues reflecting off the surface. Framed by natural foliage, the scene offers a peaceful atmosphere.

Home in Summerland Key

4.87 out of 5 average rating, 39 reviews

Powell Family Resort

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, 6 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

A sunlit deck features white lounge chairs positioned towards a private beach and ocean view. A thatched-roof tiki hut provides shade, while a hammock is nestled nearby among greenery. The calm waters reflect the blue sky, enhancing the serene coastal setting.

Home in Islamorada

5 out of 5 average rating, 3 reviews

Charming Beach House directly ON the beach

The RV interior features warm wood cabinetry and dark furnishings, creating a homey environment. A fully equipped kitchen is seen beside a cozy living area with a sofa and two armchairs. Natural light filters through the window, illuminating the space with a soft glow.

Camper/RV in Big Pine Key

4.7 out of 5 average rating, 60 reviews

LARGE LOT & RV | Fishermen Camp

A stilted house stands proudly under a bright sky, surrounded by palm trees. A gravel driveway is visible, accommodating vehicles. The exterior reflects tropical charm, showcasing a mix of light-colored siding and wooden accents while a nearby patio area offers additional outdoor space.

Home in Marathon

4.8 out of 5 average rating, 65 reviews

7 Mile Ocean Bliss

A spacious bedroom features a wooden bed frame with a plush white comforter. Decorative pillows add a touch of color against a soft green accent wall. A bedside lamp and a wooden side table complement the cozy atmosphere.

Villa in Islamorada

4.68 out of 5 average rating, 71 reviews

Picturesque Villa Near History of Diving Museum

A view from a balcony reveals a calm canal with a clear blue sky above. Palm trees sway gently in the breeze, and various boats are docked along the waterfront. The setting showcases a peaceful neighborhood with homes lining the opposite shore.

Apartment in Key Colony Beach

4.86 out of 5 average rating, 7 reviews

A slice of paradise!

A wooden dock extends into clear waters, surrounded by soft sandy shores. The sky is bright with fluffy white clouds, reflecting a peaceful coastal atmosphere. The gentle waves lap against the dock, inviting relaxation and exploration.

Townhouse in Layton

4.83 out of 5 average rating, 12 reviews

Florida Keys Getaway w/ Stunning Ocean Views

Beachfront home rentals with a pool

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

Apartment in Marathon

4.83 out of 5 average rating, 18 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

A clear view of a swimming pool is framed by palm trees and greenery. Lounge chairs are positioned alongside the pool, and the ocean can be seen in the distance. The scene conveys a relaxed outdoor atmosphere, inviting guests to enjoy the coastal surroundings.

Condo in Key West

5 out of 5 average rating, 4 reviews

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

A spacious living area features large glass doors that allow natural light to fill the room, offering views of the surrounding landscape. Comfortable blue sofas are arranged around a central coffee table on tiled flooring, complemented by a stylish armchair. Decor elements include framed pictures and modern lamps.

Condo in Key West

4.6 out of 5 average rating, 149 reviews

Colorful 2BR Oceanfront 4th-Floor | Balcony

A private screened-in balcony features a glass table set with breakfast items and a beverage. Two wicker chairs surround the table, while a guest enjoys the ocean view in the background, framed by palm trees and an evening sky.

Resort in Key West

4.89 out of 5 average rating, 9 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

A private outdoor area features a heated swimming pool surrounded by a paved deck. Lounge chairs are arranged nearby, with palm trees visible against a clear blue sky. In the distance, a tiki hut and additional lounging space enhance the tropical atmosphere.

Home in Marathon

4.79 out of 5 average rating, 34 reviews

(# 6)Waterfront Beautiful 4 Bed 3 Bath Pool Home

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

Condo in Key West

5 out of 5 average rating, 9 reviews

Hyatt Beach House-Quiet Key West Spot!

A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.

Vacation home in Marathon

4.94 out of 5 average rating, 48 reviews

Cabana Club Condo: Key Colony Beach, FL

A screened balcony offers a view of the ocean and sandy beach, framed by palm trees. A round dining table with four chairs is positioned for outdoor meals, while the large pool area is visible below, complementing the serene coastal setting.

Condo in Marathon

4.57 out of 5 average rating, 7 reviews

Oceanview Retreat w/Pool Steps Away From Beach #14

Private beachfront home rentals

Top guest favorite

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

Condo in Key Colony Beach

4.96 out of 5 average rating, 218 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

A spacious studio features a comfortable bed dressed in soft blue and white linens, complemented by decorative pillows. A cozy seating area with a light blue sofa and armchair stands nearby. Windows provide unobstructed ocean views, framed by tropical artwork and natural light.

Condo in Key Colony Beach

4.92 out of 5 average rating, 249 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

A modern living area is displayed with light-colored walls and a wood-style floor. A comfortable sectional sofa and vibrant blue seating surround a circular table. A flat-screen television mounts on the wall, and natural light enters through two windows, enhancing the bright atmosphere.

Condo in Key Colony Beach

4.97 out of 5 average rating, 251 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

A bright and airy bedroom features a spacious bed with crisp white bedding and decorative pillows. Nightstands with turquoise lamps flank the bed, and starfish art adorns the walls. Natural light filters through the shutters, creating a fresh and inviting atmosphere.

Condo in Key Colony Beach

4.91 out of 5 average rating, 237 reviews

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

A bright studio condo is shown with two queen beds, separated by privacy screens. Tropical decor includes a seahorse sculpture and dolphin wall accents. A cozy blue couch is present, accompanied by a light-colored accent chair. A dining table with floral artwork completes the inviting space.

Condo in Key Colony Beach

4.91 out of 5 average rating, 153 reviews

Seaside Whimsy - Beach and Pool, Key Colony Beach

The studio condo features two queen-sized beds with navy blue bedding and decorative pillows. A light grey nightstand with a lamp is positioned between the beds. A comfortable seating area and a low coffee table are visible, complemented by decorative items in muted colors.

Condo in Key Colony Beach

4.94 out of 5 average rating, 242 reviews

Exquisite Luxury Oceanfront Complex Key Colony

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

Condo in Key West

4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

An aerial view of a condo complex along a serene beachfront. The clear blue Atlantic Ocean stretches into the distance, while a heated pool is visible in the center of the complex. Lush palm trees and well-maintained landscaping surround the buildings.

Condo in Marathon

4.83 out of 5 average rating, 6 reviews

Beachfront Condo on Coco Plum Beach w/heated pool

Destinations to explore