Beach house vacation rentals in Key West

5.0 out of 5 average rating, 9 reviews

Grassy Key Ocean Front Beach House

HEATED POOL $150 weekly. Experience relaxed island luxury with no neighbors within a block of the property, located on Grassy Key in the Middle Keys. Perched directly on the Atlantic with an unobstructed view, the property sits on private acreage and was designed to maximize the ocean panorama from every level. Whether you want to watch sunrise from the balcony, dine under the tiki hut, beside the oceanfront pool while listening to the surf, this is a place to reconnect with family and friends.

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.

4.92 out of 5 average rating, 24 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 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

4.86 out of 5 average rating, 42 reviews

Powell Family Resort

Tranquility abounds in this unique property with fantastic sunset views, beach and a superior pool. Total privacy is yours, deep water dockage abounds on this 2.5 acre estate.. Outdoor gas grill , kayak's and paddle boards included, Tiki Bar. Master bedroom with whirlpool tub, enclosed porches, newly remodeled kitchen. A great place to gather for a large group of family time or friends. Contact for rentals less or over a weekly stay when available. May 30-June 6 available and 2 weeks in Aug.

4.99 out of 5 average rating, 75 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.

5.0 out of 5 average rating, 60 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 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.

4.94 out of 5 average rating, 93 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

A long, wooden dock extends into calm, clear waters, surrounded by an expansive sky. The surface of the water reflects the blue hues above, while the dock is bordered by ropes, inviting a sense of exploration and tranquility.

4.96 out of 5 average rating, 55 reviews

Coconut Palms in Marathon

Relax in paradise under the Coconut Palms! Enjoy everything the Keys have to offer at this extremely private 3 Bedroom 3 Bath Home with the best view of the Florida Bay sunsets! This dock’s fishing spot is the best kept secret while also getting to experience tons of amazing sea life in your backyard! Have fun in the heated pool while watching your favorite shows in the brand new tiki hut or sit by the fire pit under the stars! You are welcome to come and stay in the most beautiful place!

4.94 out of 5 average rating, 33 reviews

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

Home in Cudjoe Key

Oceanside home 109, 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 #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 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 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.

4.85 out of 5 average rating, 111 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.

5.0 out of 5 average rating, 12 reviews

P01 - New 3 bed, 3 bath with private pool

This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom

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.

4.88 out of 5 average rating, 16 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

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