Mansion vacation rentals in Key West

The outdoor area features a private swimming pool accompanied by a spa, surrounded by lush palm trees. Colorful lounge seating is available nearby, and a staircase leads up to the elevated house, which is situated in a tranquil, well-maintained garden.

4.96 out of 5 average rating, 45 reviews

Dock Pool Home by Sombrero Beach

This spectacular home is in the heart of Paradise. Sombrero beach just a few blocks away, Golfing across the street and your boat in our dock, everything you need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis. The golf course is directly in front of the home. The home offers a private swimming pool with spa. There is 75' of deep water dockage which offers a straight shot out to the Ocean or Bootkey VACA-21-493

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!

5 out of 5 average rating, 6 reviews

Aerial view showcasing the charming townhomes surrounded by lush greenery and vibrant palm trees. The turquoise water reflects the clear sky, with boats docked along the canal. The neatly arranged front gardens add to the inviting atmosphere of the neighborhood.

Townhouse in Marathon

Discount to Jan 31! 4 /3, 32' Dock, Cabana Club!

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE! - Upstairs Master w/ king & en suite bathroom - 1 guest room downstairs w/ queen size bed - A full bath is located on the first floor. Perfect for individuals who have trouble navigating stairs. - 2 identical guest bedrooms upstairs, each w/ a queen size bed and balcony - Full bath upstairs (hall, shared with two guestrooms) WHAT TO EXPECT AT SALT & SKY: -Fully stocked kitchen with everything you

Superhost

A serene outdoor space features a sparkling pool with a connected spa, surrounded by lush palm trees. A wooden dock extends toward the open water, enhancing the coastal ambiance, while two lounge chairs sit invitingly nearby.

4.8 out of 5 average rating, 41 reviews

Horizon

Horizon is a bright beautiful upscale home, custom designed to take full advantage of its unique ocean location. Every room, has a wide sliding glass door to oceanfront balconies. Every bedroom has a private bath. Pool with Spa, Observation Platform for those sunrises on open water, ping pong, corn toss, kayaks and paddle boards, multiple dining areas, WIFI, quality appliances, comfy cotton bedding, crib, high chair multiple TV's poolside loungers, rocking chairs & bird watching. ++++

Aerial view of the property reveals a pair of modern houses with metal roofs, surrounded by lush greenery. A turquoise pool glistens amidst the outdoor space, adjacent to a wooden dock along the calm canal waters. The setting reflects a serene vacation atmosphere.

5 out of 5 average rating, 17 reviews

Extra Lux Grouper House w/4 Master Suites, 6 BA,

This gorgeous home from the "Happy In The Keys" collection offers equal 4 Master Suites with king-sized memory foam beds, private bathrooms with individual coffee/wine bars, smart TVs, and expansive patio space. The dining, kitchen and living areas share a gorgeous sunset view over the ocean canal. A 55 inch flat screen television is in the living area, a half bath is off the great room. A covered porch looks over the pool and canal. The pool has a large deck, a half bath and an outdoor shower

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 out of 5 average rating, 39 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 tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

5 out of 5 average rating, 59 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with a pool table & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable beds for a perfect night's rest

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.

A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

5 out of 5 average rating, 42 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

4.88 out of 5 average rating, 16 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.

A spacious outdoor deck features comfortable seating and a large mural of a marlin. Sunlight reflects off the turquoise water in the canal, while palm trees sway in the gentle breeze, creating a relaxing atmosphere for guests.

5 out of 5 average rating, 14 reviews

NEW: Vaca Cut with 60' dock, 4br-4ba, 2 kitchens

Boaters and anglers, welcome to paradise! This renovated 4BR/4BA home just off Vaca Cut offers unbeatable Ocean and Bayside access, a 60’ dock, cleaning station, and a dock power station. Relax on the two-story waterfront deck, spot dolphins and manatees, or head out for world-class fishing just minutes away. With two kitchens, two living rooms, 4 bathrooms and plenty of space, it's perfect for families, friends, or couples looking to unwind and explore the best of the Florida Keys!

The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.