Mansion holiday rentals in Key West

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Top-rated mansion rentals in Key West

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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, 24 reviews

New Luxury Oceanfront House. Hot Tub & Sunset 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
Home in Marathon
5 out of 5 average rating, 17 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

Guest favourite
The sailing catamaran Purpus is shown gliding over the water, featuring a sleek white hull and a large deck. A spacious area is visible at the bow with crew members actively adjusting the sail. The overall design emphasizes both function and elegance.
Boat in Key West
4.9 out of 5 average rating, 30 reviews

Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.

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Villa in Key Colony Beach
5 out of 5 average rating, 3 reviews

Deep Blue ~ Waterfront Gem ~ Pool ~ Kayaks ~ Dock

Escape to the stunning Deep Blue, a 4BR 3BA waterfront retreat in the exclusive Key Colony Beach, Florida Keys. This expansive two-story estate offers the ultimate island getaway with its sophisticated design, luxurious amenities, and breathtaking water views from your private 112-foot dock. ✔ 4 Luxurious BRs ✔ Gourmet Kitchen ✔ Heated Swimming Pool & Spa ✔ Waterfront Yard (Fire Pit, BBQs, Games, Kayaks, Bicycles) ✔ 112ft Private Dock (Fishing Station, Water, Electricity) ✔ Smart TVs Throughout

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, 10 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

Top Guest favourite
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.
Home in Marathon
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!

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.

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, 127 reviews

Angler’s Terrace Conde 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

Guest favourite
A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.
Home in Summerland Key
4.95 out of 5 average rating, 97 reviews

Waterfront Anchor House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Top Guest favourite
A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

Guest favourite
Home in Marathon
4.95 out of 5 average rating, 140 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

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