Beachfront vacation rentals in Stock Island

Tiny home 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.

4.8 out of 5 average rating, 20 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 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

Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

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.

4.89 out of 5 average rating, 19 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

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 favorite

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, 20 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.

4.91 out of 5 average rating, 11 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.

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.

4.97 out of 5 average rating, 110 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.

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

A private swimming pool is situated in a sunlit outdoor space, surrounded by lounge chairs. The two-story home features a spacious balcony with ceiling fans, offering views of palm trees and a vibrant blue sky.

4.85 out of 5 average rating, 26 reviews

(#8)Waterfront 4 Bed 3 Bath Pool Home w Free Dock

🌸Home #8 "DEJA⛵BLUE" Full Premium WATERFRONT view of Beach, Docks and Ocean🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA 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.

4.82 out of 5 average rating, 120 reviews

A private beach scene features four adirondack chairs in white and turquoise, positioned in soft, sandy areas under palm trees. The calm ocean extends to the horizon, with a distant dock visible on the water. Bright clouds hover in a blue sky.

Home in Sugarloaf Key

The Guest House - Sugarloaf Beach Key West

One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree * "Dock is currently undergoing maintenance, dockage will not be available until further notice"

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.

Popular amenities for Stock Island beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.93 out of 5 average rating, 28 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

4.88 out of 5 average rating, 40 reviews

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, 7 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, 34 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

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, 97 reviews

Palm - Beach Houses Key West

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, 262 reviews

Key West Luxury Houseboat at Yacht Club Resort

Beachfront home rentals with a pool

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 serene pool area is surrounded by lounge chairs with striped canopies, offering a relaxing atmosphere. Palm trees sway gently in the breeze, while the backdrop features the resort buildings set against a clear sky. Lush green grasses border the scene, enhancing the natural beauty.

Marathon Oceanfront | 2 King Beds + Balcony

A spacious outdoor pool area is surrounded by lounge chairs beneath tall palm trees. The pool is illuminated in gentle light, reflecting the calm waters in the background. A tiki bar is visible, offering a welcoming setting for relaxation.

Apartment in Marathon

Marathon 1BR Villa on Lovely Waterfront Resort

A waterfront view showcases the serene Gulf of Mexico, flanked by swaying palm trees. The marina is visible with several boats docked, while the vibrant blue water contrasts with the lush greenery in the foreground. A clear sky enhances the tranquil atmosphere.

Apartment in Key West

Waterfront Galleon Marina+Beach, Near OldTown, 1BR

The outdoor area features a clear view of the ocean, lined by swaying palm trees. A tranquil pool is visible, accompanied by lounge chairs and white umbrellas. Beachside tables are arranged under string lights, creating a relaxed atmosphere for guests to enjoy.

Marathon Oceanfront Suite | Balcony + Dog-Friendly

A serene pool area is surrounded by lush palm trees and provides multiple lounge chairs with blue and white striped canopy umbrellas. The water in the pool glistens under a clear blue sky, enhancing the inviting relaxation experience.

Marathon Oceanfront Room | 2Queens + Spa-Like Bath

A marina features several boats docked along a wooden pier, with lush mangroves visible in the background. The clear blue sky is dotted with fluffy white clouds, creating a serene atmosphere for marine activities.

Apartment in Key West

Waterfront Marina 2BR Mallory Condo+Amenities

A private oceanview terrace is presented, furnished with two comfortable chairs and a round table. Lush palm trees are visible in the background, framing the serene view of the ocean. Natural light enhances the welcoming atmosphere of this outdoor space.

Marathon Oceanfront | ADA Queen + 5 Pools

Private beachfront home rentals

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.

Condo in Marathon

Marathon 1BR Villa on Lovely Oceanfront Resort

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

4.89 out of 5 average rating, 9 reviews

New place to stay

Suite Sanctuary at the Beach

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

Hyatt Windward Pointe Resort: Beachfront Condo

A spacious outdoor pool is surrounded by lounge chairs, with palm trees lining the area. A tiki bar is visible in the background, offering shaded seating and a view of the water. Evening lighting enhances the tropical ambiance.

Condo in Marathon

Marathon 1BR Villa on Lovely Oceanfront Resort

Apartment in Marathon

Marathon 1BR Villa on Lovely Gulf Front Resort

4.92 out of 5 average rating, 24 reviews

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.

Home in Cudjoe Key

Oceanside home 107,dock,kayaks,bikes,pool,fishing,