Mansion vacation rentals in Florida Keys

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

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, 106 reviews

Beautiful Waterfront book now Thanksgiving is Open

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.

4.88 out of 5 average rating, 113 reviews

A two-story home is set against a backdrop of vibrant greenery, with a private in-ground pool visible in the foreground. A white fence outlines the pool area, while steps lead to a spacious balcony above that overlooks the pool.

Home in Key Colony Beach

Pet Friendly Half Duplex Pool Home with Boat Slip

Want a spacious home with private pool and dock? You have found it! On a deep water canal. Enough dock space for a 37' boat. Enjoy your private heated pool or lounge in the shade or sun Easy walking to restaurants, shops, golf course, park, playground and entertainment. YOU MUST AGREE TO THE CITY'S RULES, IF YOU BOOK. Pool heater optional. $50/night or $250/week Any reservation starting after 6/13/23 will NOT include access to the Cabana Club but that will be available for a daily fee.

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

4.98 out of 5 average rating, 120 reviews

An aerial view of a blue, two-story house surrounded by greenery. The backyard features a swimming pool, red umbrellas, and seating areas. A patio leads to the pool, and the front yard is landscaped with grass. The neighborhood shows a quiet street with nearby houses.

Home in Key Largo

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.

✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

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, 102 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 outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.

4.89 out of 5 average rating, 74 reviews

Gorgeous Ocean View Home!

Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144

A serene pool area is framed by palm trees and lush greenery, offering views of the ocean. Comfortable lounge chairs are positioned around the pool, which features a spa. The scene includes bright umbrellas, enhancing a relaxing outdoor space under a clear blue sky.

4.98 out of 5 average rating, 52 reviews

Oceanfront with Pool near Sombrero Beach

<b>Welcome to Seascape Point!</b><br /><br /> Perfectly situated at the end of a quiet block, this stunning fully-renovated house is the perfect place to relax and unwind in between your sightseeing or fishing excursions. The house sits on an oversized lot that juts into the ocean to offer amazing water views from every angle. Its incredible location next to a nature preserve provides you with unparalleled privacy plus daily sightings of exotic, tropical birds.

A spacious rooftop area features a sleek design with areas of artificial grass and modern pavers. The sunset casts warm hues across the sky, with views of the Gulf waters visible in the background. Outdoor seating and a bar are positioned on one side.

4.89 out of 5 average rating, 38 reviews

The Bent Coconut

A modern masterpiece in the heart of the Florida Keys. Breathtaking views of the Gulf from every room. Stunning rooftop, with outdoor bar, seating, lounge chairs, and shower. One of a kind infinity edge pool on the second floor, and a second mini-pool on the ground level with a second outdoor kitchen. Glass elevator with a floating staircase surrounding it brings you up to the second floor great room. The open layout is perfect for entertaining. VACA-23-114

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.