Mansion holiday rentals in Florida Keys

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Top-rated mansion rentals in Florida Keys

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Top guest favourite
The image showcases a modern two-story home with a light blue exterior, surrounded by lush landscaping. A heated pool is visible in the foreground, alongside kayaks and paddle boards. The ocean view offers clear, open water, enhancing the tranquil setting of 'The 7-Mile Villa.'
Home in Marathon
5 out of 5 average rating, 23 reviews

Seagrass-Free • New 5BR Pool Home w/ Ocean View

Brand new build 2024. This 5 bed/4bath luxury ocean gulf home with boat dock, heated/chilled pool/ spa, paddle boards kayaks, bicycles was meticulously designed and custom built like no other house in Marathon Key. You can see ocean water from every room in the house. and the interior design was chosen to maximize comfort, with a stress-free peaceful setting. Only three homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

Top guest favourite
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.
Home in Marathon
5 out of 5 average rating, 62 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 Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

Top guest favourite
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
4.95 out of 5 average rating, 146 reviews

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!

Guest favourite
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
5 out of 5 average rating, 7 reviews

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

Guest favourite
A serene beach scene features a calm turquoise ocean under a clear blue sky. Two loungers in contrasting colors sit on the sandy shore, and a wooden dock extends into the water. A palm tree sways gently in the breeze, enhancing the tranquil setting.
Home in Islamorada
4.96 out of 5 average rating, 24 reviews

Islamorada Home 5/3 Private Beach! freshly updated

Relax in Islamorada, Enjoy the day deep sea fishing, and watch the sunset at our private beach. Our 5/3 House is freshly updated. Master has a king bed and the two others have full beds with trundles underneath to sleep 3 or 4 kids, 2 more bedrooms downstairs with 1 king size bed, and 1 king and twin bed, Freshly furnished, and the bathrooms are freshly updated as well. The boat dock can hold up to a 40 ft boat with power and water at the dock there is a lot to do and see in the keys!

Guest favourite
An aerial view captures the oceanfront estate featuring a spacious house with a light green roof. A private pool is surrounded by lounge chairs, while kayaks rest on the sandy area by the water. A long pier extends into the clear, shallow water, framed by palm trees.
Home in Marathon
4.83 out of 5 average rating, 30 reviews

Million Dollar View

Take it easy at this unique and tranquil getaway. Enjoy endless open water views from anywhere on this acre-sized, OCEAN FRONT Gulf-side estate. Coconut palms, private hot tub & pool, boat ramp, and a 285 foot long private pier great for catching fish and spectacular sunsets. Like a private resort, you can play giant chess on the beach, win at ping pong, take out a kayak, or paddle board or stroll through fabulous gardens with no staff to tip. License VACA-23-190, VACA 24-285

Top guest favourite
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.
Home in Marathon
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.

Guest favourite
Villa in Key Largo
5 out of 5 average rating, 14 reviews

The Lookout #48 Full Ocean View Luxury Villa |

Discover a serene vacation rental where luxury meets tranquility. Ocean Residences offers modern design, a secluded retreat vibe, and access to the exclusive amenities of Playa Largo Resort & Spa, including pools, dining, and beachside relaxation (wristband required). Pet-friendly with a stunning clubhouse and Atlantic views, this destination ensures unforgettable memories. Complimentary shuttle service makes exploring effortless. Book your ultimate getaway today!

Guest favourite
Home in Marathon
4.96 out of 5 average rating, 24 reviews

Emerald Oasis ~ Lux Waterfront Gem ~ Pool ~ Kayaks

Indulge in this luxurious 4BR 4.5BA house nestled on a gorgeous waterfront property in Marathon, FL. This spacious estate offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, and scenic outdoors with the private fishing dock. ✔ 4 Comfortable BRs ✔ Swimming Pool ✔ NEW! Private Putting Green ✔ Yard (Fire Pit, BBQs, Games, Bicycles) ✔ 75ft Dock (Fishing Station, Water, Electricity) ✔ Deck ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking

Top guest favourite
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.
Home in Marathon
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.

Top guest favourite
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.
Home in Marathon
4.97 out of 5 average rating, 126 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Superhost
Home in Marathon
4.83 out of 5 average rating, 12 reviews

P98 - 4 bed, 4 bath home with dockage and private

This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention given to each and every detail. This property is warm and inviting and located in the desirable neighborhood of Sombrero Beach. This home is perfectly positioned on the property to maximize full use of the grounds, providing ample parking in the front, while creating an abundant outdoor living space in the back.

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