Mansion vacation rentals in Key West

5 out of 5 average rating, 20 reviews

Waterfront 6BR Luxury Retreat w/ Pool & Dock

Welcome aboard Captain's Retreat, your 6BR/5BA tropical paradise in Marathon with 80 feet of dockage for up to 3 boats! I expanded from our popular Captain's Quarters to create this ultimate family compound with fast ocean access. Cruise the Atlantic on our premium Hobie kayaks, challenge family to shuffleboard by the heated pool, or rack 'em up in the billiards room – there's something for every generation in your crew! 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 80ft dock with Hobie pe

4.95 out of 5 average rating, 146 reviews

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

A spacious deck is visible, offering a view of the Gulf of Mexico and a nearby dock. Comfortable outdoor seating is arranged against the backdrop of lush greenery and a sandy shoreline, providing a relaxing setting to enjoy the scenery.

4.82 out of 5 average rating, 108 reviews

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

The modern beach house is set against a tranquil waterfront backdrop, featuring light-colored siding and a metal roof. Lush palm trees and landscaped grounds surround the property, complementing the natural waterfront area. The structure is elevated, with a staircase leading to the main level.

4.92 out of 5 average rating, 24 reviews

Salty Kisses Beach House

Salty kisses is a Modern brand new construction 5/4 beach house with a pool and a dock Salty kisses is a piece of paradise in Marathon. Gorgeous brand new 5 bedrooms,4 bathrooms single family home with open balconies to capture the breeze and enjoy with your family and friends. The space Five bedrooms, Four bathrooms First level has a bathroom/bedroom with the living room, Kitchen and dining room. Second floor The master suite that takes your breath away. The kids bedroom has 2 bulk beds

A modern waterfront home, known as 'The Lighthouse', is displayed with expansive open water views. The image captures a heated pool and a boat dock, surrounded by lush landscaping, illustrating the inviting outdoor space for relaxation and entertainment.

5 out of 5 average rating, 28 reviews

Oceanfront . 5br Luxury . Hot tub. January Special

Escape to this new stunning waterfront pool home. Enjoy panoramic ocean views, a private boat dock, with , fishing area, snorkeling, kayaks, paddle boards, bicycles and more.... The spacious, modern interior features a fully equipped kitchen, cozy bedrooms, and an open living area perfect for relaxation. Step outside to a beautiful patio or two balconies with seating to take in the views. Ideal for multiple couples, big families, or friends looking to explore the best of the Marathon key.

Superhost

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

4.77 out of 5 average rating, 13 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.

4.89 out of 5 average rating, 18 reviews

A private pool is surrounded by wooden decking and lounge chairs, set against a backdrop of lush greenery leading to the water's edge. The Atlantic Ocean can be seen in the distance under a clear blue sky, creating a serene outdoor space.

Home in Cudjoe Key

Blue House - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our vacation rental homes staying between the dates of September 1st through Dec 20, 2025. Please reach out before booking for boat availability. Vacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom and 2 bathrooms. Large dock with water access for a small boat.

An inviting outdoor area features a clear swimming pool surrounded by a paved patio. The two-story structure above includes spacious balconies with multiple seating options. Sunlight brightens the scene, and lush greenery is visible in the background, enhancing the tranquil environment.

4.97 out of 5 average rating, 104 reviews

Angler's Eden

Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks and a paddle-board. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

Superhost

The exterior of the modern home showcases a spacious backyard featuring a heated swimming pool, fire pit, and lounge chairs. Lush green grass surrounds the paved pathway leading to the entrance, with the house's contemporary design highlighted against a colorful sunset backdrop.

Villa in Marathon

5 out of 5 average rating, 3 reviews

Ocean Muse - Lux Waterfront Escape - Pool - Dock

Step into Ocean Muse, a luxurious 4BR 3Bath waterfront escape in peaceful Marathon, FL! Enjoy a private backyard with heated pool & spa, fire pit, dock, elevator, and stunning ocean views at Ocean Muse—just minutes from top attractions. ✔ 4 BRs (2 Master Suites, Bunk Room) ✔ Open‑Design Living ✔ Full Kitchen + Wet Bar ✔ Backyard w/ Lounge, Pool, Fire Pit, Games, BBQ ✔ 40' Dock w/ Fish Station ✔ Rooftop Ocean Views ✔ Elevator to All Levels ✔ Minutes from Top Attractions

Superhost

A wooden dock extends into clear waters, framed by a serene natural landscape. The surrounding area includes greenery and several beach houses visible in the background under a bright blue sky with scattered clouds.

Home in Summerland Key

4.7 out of 5 average rating, 79 reviews

Beach House Key West, with a daily rentals license

This listing is one of the very few beach houses with a daily, rental license in the Key West area. A unique island experience awaits you in the spacious and peaceful oceanfront house. The property is perfect for a family or friends gathering. House has a beautiful oceanfront pool, the pool is not heated, big yard, outdoor grill, and barbecue. The dock is is steel dock located in a deep water canal, the control depth is 6' It was recently rebuilt.

4.82 out of 5 average rating, 100 reviews

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.