Beachfront vacation rentals in Stock Island

Tiny homes 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.

4.81 out of 5 average rating, 21 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

A two-story home is depicted, featuring a covered balcony with blue chairs and a ground-level terrace. A kayak is positioned nearby on gravel, alongside two adirondack chairs near natural landscaping. The surroundings are lush with greenery, enhancing the tranquil setting.

4.9 out of 5 average rating, 20 reviews

Boaters delight! 1 min to open water, Dock & Beach

Inquire for monthly discounts. The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

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.

4.75 out of 5 average rating, 99 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.

A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.

4.93 out of 5 average rating, 83 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

Blue Treasure at Sombrero Beach is a 2020 built single-family home in a private community within walking distance to the beautiful Sombrero beach and 5 minute boat ride to the ocean. This house is a private fully equipped 4/3 that has three king memory foam beds and one queen memory foam & queen sofa memory foam. All the rooms have a TV w/ cable & Netflix. We also have a separate downstairs area that we provide kayaks, paddle boards, and bicycles at no additional cost. License #:VACA-20-150

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, 22 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.

4.92 out of 5 average rating, 12 reviews

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

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.

4.93 out of 5 average rating, 30 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

Get ready to indulge in a relaxing and unforgettable experience at the original houseboat getaway! 🌴What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! enjoy 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

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.

4.86 out of 5 average rating, 58 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

1BR 1BA ocean front suite with a living room, kitchen and one bedroom. Doors that open to a balcony overlooking the Atlantic Ocean. Heated pool, hot tub, sun deck and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street and the most Southern Point. Located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. Free garage parking. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy central a/c.

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.

4.83 out of 5 average rating, 6 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

4.8 out of 5 average rating, 35 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!

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, 37 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.

4.85 out of 5 average rating, 41 reviews

New place to stay

Beach Home and Boater’s Paradise Sombrero

Your Private Florida Keys Paradise Steps to Sombrero Beach Waterfront • Private Pool • 50 ft Dock • Direct Ocean Access Welcome to your dream escape in Marathon, the heart of the Florida Keys and the world’s fishing capital. This 2-bedroom, 2-bathroom coastal home offers everything guests come to the Keys for sun, sand, boating, and pure relaxation. Renta Lic: VACA-2025-205

Popular amenities for Stock Island beachfront rentals

Kitchen

Wifi

Pool

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

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, 94 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

5 out of 5 average rating, 9 reviews

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

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

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.

4.74 out of 5 average rating, 38 reviews

Breathtaking Waterfront Hotel w/ / Outdoor Pools

Camper/RV 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 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

4.83 out of 5 average rating, 266 reviews

Key West Luxury Houseboat at Yacht Club Resort

4.33 out of 5 average rating, 6 reviews

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.

Home in Cudjoe Key

Oasis

Beachfront home rentals with a pool

A serene pool area is surrounded by tropical palm trees and lush greenery. The clear water reflects the bright sky, while lounge chairs with umbrellas are arranged neatly around the pool's perimeter, offering a relaxing space for guests.

Traditional 2 Queen, The Pier House, Beach Access

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

The room features two queen beds with white linens, complemented by bedside lamps. A large television is mounted on the wall opposite the beds, with a sleek dresser beneath it. French doors provide access to a patio with garden views, enhancing the space's natural light.

Serene Resort w/ Private Beach & Spa in Key West

A private balcony offers panoramic ocean views, featuring two lounge chairs with folded towels. A cozy sectional sofa with decorative pillows is positioned beside swaying palm trees, while the tranquil sea horizon stretches into the distance. Soft natural light illuminates the relaxation area.

Oceanfront Suite, The Pier House, Beach Resort

An outdoor balcony space features a round table surrounded by two armchairs and a spacious sofa, all in light wicker with patterned cushions. Palm trees frame the serene ocean view, creating a relaxing retreat.

5 out of 5 average rating, 3 reviews

Oceanfront Balcony King, Isla Bella, Beach Resort

An outdoor dining area features elegantly set tables with clean white linens, surrounded by beige wicker chairs. Large umbrellas provide shade against the blue sky and distant ocean views. Potted greenery adds a touch of nature, creating a relaxed atmosphere for guests.

2 Traditional Two Queen, Pier House, Near Duval St

An outdoor terrace overlooks the ocean, featuring a glass-topped table and comfortable seating. Lush palm trees sway gently in the breeze, and the tranquil waters glisten under bright sunlight, creating a serene backdrop to the private retreat.

Marathon Oceanfront Suite | Balcony + 2 Luxe Baths

A hotel room features two spacious queen beds with white linens, complemented by a wooden headboard. A large flat-screen TV is mounted on a dresser, and natural light filters in through multiple windows adorned with wooden shutters, creating a bright and inviting ambiance.

Lanai Two Queen, The Pier House, Beach Access

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.

Apartment in Key West

Beach House Resort + Premium Amenities, 2BR Condo

A balcony view reveals the expansive Atlantic Ocean, featuring a peir extending into the water. Palm trees are visible, adding a tropical ambiance. The serene blue waters and clear sky harmonize in the background, enhancing the coastal experience.

4.9 out of 5 average rating, 94 reviews

Ocean Front Studio private Sandy Beach in Key West

New place to stay

Ocean Dream – Your Private Beach + Pool (M#31)

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, 151 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

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.

4.8 out of 5 average rating, 25 reviews

Oceanfront Key West Condo

4.4 out of 5 average rating, 10 reviews

Beautiful Beachfront Home w/Heated Pool-45' Dock