Mansion holiday rentals in Florida Keys

5 out of 5 average rating, 8 reviews

Oceanfront Rooftop Views w/ 75ft of Dockage

Welcome aboard Captains Rooftop, Your 4BR Rooftop Deck Hot Tub Oasis on a direct ocean access canal with 75ft of dockage. This three story stilted rooftop home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ 2 Luxury jet Hot Tubs (One on the roof, one in the backyard) ⛵ Private 75ft dock surrounded by a mangrove jungle 🕹️ Foosball Table 🍳 Rooftop patio with BBQ grill & open ocean view dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

A spacious outdoor area features a heated swimming pool surrounded by sun loungers. A covered patio provides dining seating, while a blue umbrella offers shade. The elevated home above enhances the relaxing ambiance, complemented by light-colored flooring and lush greenery.

4.95 out of 5 average rating, 22 reviews

Luna Light ~ Waterfront ~ Pool ~ Dock ~ Views!

Bring your family to the stylish 4BR 4.5Bath home in a tranquil waterfront area, and enjoy an unforgettable stay with your loved ones. Explore nearby attractions from this prime location, or spend the day soaking up the sun by the pool, fishing from the dock, savoring tasty BBQs, and much more! ✔ 4 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Outdoors (Heated Pool, Lounges, Dining, Games) ✔ Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking (4 Cars + Trailer) ✔ Ev Charger See more bel

4.95 out of 5 average rating, 149 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.

A stunning view of 'The Islander' Villa overlooks open water, showcasing a spacious heated pool with surrounding patio areas. Lush palms sway in the breeze, and the two-story home features large balconies designed for enjoying the scenic surroundings.

5 out of 5 average rating, 19 reviews

World-Class Oceanfront Pool/Hottub Sunset Escape

Escape to Oceans Cay Villas—luxury oceanfront in the Florida Keys. Features: ✨ Heated swimming pool ✨ Relaxing hot tub ✨ Fire pit with perfect sunset views ✨ Private dock for your boat ✨ Walk or ride to Seven Mile Bridge ✨ Free kayaks, paddle boards, and bicycles ✨ Ping pong table ✨ Fishing, snorkeling, and swimming in your backyard ✨ Walking distance to restaurants and attractions ✨ Stylish, modern villa design ✨ Privacy and comfort for couples, families, or friends ✨No seagrass smells!

4.99 out of 5 average rating, 136 reviews

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, 105 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

A serene outdoor space is highlighted by a white gazebo and lounge chairs positioned around a fire pit. Lush palm trees frame the area, with a clear view of the water and a dock in the background, creating a peaceful setting for relaxation.

4.88 out of 5 average rating, 81 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

4.82 out of 5 average rating, 103 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.

4.97 out of 5 average rating, 131 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

4.95 out of 5 average rating, 102 reviews

A charming waterfront home is surrounded by palm trees and colorful landscaping. A gravel driveway leads to a welcoming entrance with a porch. The turquoise facade complements the bright blue sky and ocean in the background, highlighting the property's coastal appeal.

Home in Summerland Key

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!

Superhost