Beachfront holiday rentals in Stock Island

Campervan/Motorhome in Big Pine Key

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.

4.79 out of 5 average rating, 19 reviews

RV In The Keys | Tropical Retreat

Tropical retreat in the heart of Florida Keys. Relax island-style in this private & clean RV - just 30 miles from Key West and 20 from Marathon. Enjoy breezy indoor/outdoor living with a fold-down patio, 2 TVs, full kitchen, bathroom, pantry. Nestled in a local RV park with a pool, fish station, and coin laundry. Vacation here & swim in the ocean —Next to Pine Channel and 10 miles toBahai Honda State Park. Walk to groceries, Walgreens, & local eats. No park/additional fees. Big Pine Key Retreat!

4.9 out of 5 average rating, 159 reviews

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Home in Upper Sugarloaf Key

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.

4.74 out of 5 average rating, 96 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.

5 out of 5 average rating, 18 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.

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.

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.

A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.

4.9 out of 5 average rating, 69 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

Top guest favourite

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.

4.97 out of 5 average rating, 108 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 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.

4.79 out of 5 average rating, 34 reviews

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

🌸Home #6 FANTA🐬SEA WATERFRONT!🌸 Look out on the Ocean in your Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA (sleeps 10+) with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

4.89 out of 5 average rating, 123 reviews

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

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 hand holds a tall, fluted glass filled with a yellow beverage against a backdrop of palm trees and the Atlantic Ocean. The clear blue sky complements the tranquil scene, with greenery visible in the foreground and a beach path in the distance.

5 out of 5 average rating, 36 reviews

Key West Condo with Balcony Ocean View

Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

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

Experience this tropical paradise as you relax in a family friendly timeshare within the Hyatt Residence Club. Have breakfast on the oceanfront balcony followed by a dip in the pool/hot tub or visit the nearby spa. There are 2 bedrooms and 1 sofa bed which can fit 6 people. 2 bathrooms with a spa tub in master bedroom. Fully functioning kitchen and dining area in addition to an in-home washer/dryer unit.

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.85 out of 5 average rating, 259 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

Popular amenities for beachfront rentals in Stock Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.92 out of 5 average rating, 26 reviews

A single kayak glides through a serene mangrove tunnel, surrounded by lush greenery. The still water reflects the vibrant foliage above, creating a calming atmosphere. The branches arch gracefully overhead, providing a sense of enclosure in this natural waterway.

Houseboat in Marathon

Adventurers escape breathtaking off-grid houseboat

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

4.88 out of 5 average rating, 40 reviews

Powell Family Resort

A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.

Home in Summerland Key

4.59 out of 5 average rating, 93 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Apartment in Summerland Key

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.

5 out of 5 average rating, 7 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Campervan/Motorhome in Big Pine Key

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.

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.

4.8 out of 5 average rating, 65 reviews

7 Mile Ocean Bliss

A large swimming pool is surrounded by a protective fence, showcasing a connected spa. Sun loungers are placed around the pool, while tropical plants and stones enhance the outdoor setting. The serene ocean view is visible in the background.

4.2 out of 5 average rating, 5 reviews

Oasis

A view from a balcony overlooks a private white sand beach and the turquoise waters of the ocean. Lush palm trees surround the area, while the hotel building is seen with large windows accommodating guests. Sun loungers and umbrellas are arranged along the beach.

Hotel room in Key West

Seaside Getaway! Gym, Spa, Pool Harbor Access

Beachfront home rentals with a pool

A spacious hotel room features a king-sized bed with crisp white linens, complemented by a dark wooden headboard. A ceiling fan is visible above, while a television and dresser provide practical amenities. Artwork adorns the walls, and natural light is introduced through a partially opened door leading to a hallway.

Hotel room in Key West

Elegant Stay! Pet-friendly, Pool, Near Cliff Walk!

The image displays a vibrant pool area surrounded by palm trees, with sun loungers arranged near the water. A tiki bar and restaurant are positioned along the marina, offering views of the lagoon and nearby boats. The ocean glistens under a clear sky.

Apartment in Marathon

Marathon 1BR Villa on Lovely Oceanfront Resort

A serene beach area is framed by palm trees, featuring sun loungers under blue umbrellas. Soft sand leads to clear water that gently meets the shore, creating a tranquil atmosphere. The landscape is complemented by lush greenery, enhancing the coastal setting.

Marathon Oceanfront Suite | King Bed + Kitchenette

A spacious outdoor area features a shared pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over the seating arrangements. The ocean is visible in the background, showcasing tranquil blue waters. Pathways lead to the pool area, enhancing accessibility.

4.79 out of 5 average rating, 29 reviews

Breathtaking Waterfront Hotel w/ / Outdoor Pools

A spacious hotel room features two ample beds with crisp white linens and a serene blue accent wall. A desk and a comfortable chair are positioned against a light wood wall. A flat-screen TV is mounted above the desk, and a seating area includes a modern chair.

2 Relaxing Units | Pools | Near Sumbrero Beach

An aerial view of the beachfront resort is displayed, showcasing a series of white buildings nestled among lush greenery and sandy areas. The setting sun casts a warm glow over the landscape, highlighting the proximity to the water and the nearby bridge.

Marathon Beachfront | King Bed + Veranda

An aerial view showcases a large outdoor pool surrounded by palm trees, with lounge chairs positioned nearby. The infinity pool merges with the ocean, reflecting the soft hues of a sunset in the distance, while a sandy beach extends along the shoreline.

Scenic Resort Getaway w/ Private Beach & 5 Pools

5 out of 5 average rating, 4 reviews

Galleon-Walk to Duval & Mallory Square!

Private beachfront home rentals

A screened-in balcony features a wooden dining table surrounded by sturdy chairs with bright yellow cushions. A comfortable seating area includes a dark wicker chair and a gray sofa, while palm trees sway gently in the background, enhancing the tropical atmosphere.

Flat in Key West

Beach House Resort + Premium Amenities, 2BR Condo

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.

Apartment

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

A private balcony is furnished with a glass-top table and woven chairs, offering a serene view of palm trees and a sandy beach area. The calm water reflects a clear sky, creating a peaceful atmosphere for relaxation.

4.74 out of 5 average rating, 19 reviews

#7 Waterfront 4Bed 3Bath Pool Home

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.

4.59 out of 5 average rating, 150 reviews

Colorful 2BR Oceanfront 4th-Floor | Balcony

5 out of 5 average rating, 4 reviews

A spacious outdoor pool area is surrounded by lounge chairs and palm trees, creating a calm ambiance. The pool is illuminated in soft light, with a tiki bar visible in the background, offering a relaxing spot for guests to enjoy beverages while overlooking the water.

Apartment in Marathon

Marathon 2BR Waterfront Property on Lovely

A spacious bedroom is furnished with a large bed layered in neutral linens. Shuttered windows provide natural light and a view of lush greenery. A patterned armchair adds comfort to the room, creating a relaxing retreat.

4.5 out of 5 average rating, 8 reviews

Galleon Resort - Walk to Duval & Mallory Square!

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.

4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

A waterfront view of a series of light-colored homes with multiple balconies, situated along the edge of a calm bay. Colorful Adirondack chairs are arranged on the porch, and a wooden walkway leads towards the structures, enhancing the coastal ambiance.