Mansion vacation rentals in Florida Keys

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 private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 19 reviews

Waterfront home w/pool, dock & close to beach

Looking for the perfect home for your next Florida Keys vacation? Our Waterfront home with over 30 feet of dock space is Just a short boat ride out to open water for a day of fishing, snorkeling or cruising around. Our home features your own private dock & private pool... complete with chaise lounges, outdoor dining, gas grill, Adirondack chairs, fish cleaning station, bait freezer & so much more! Lastly, everyone is sure to enjoy water views & sunsets from our balcony that never disappoint

4.99 out of 5 average rating, 138 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.

A heated pool is situated in the backyard, surrounded by lounge chairs. Lush palm trees and a view of the waterfront create a serene outdoor space, with gentle clouds drifting across a bright blue sky.

5 out of 5 average rating, 39 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Entire Waterfront Home. 5 Bedroom, 4 Full Baths, Heated Pool with attached Jacuzzi Tub, Tiki Hut, Ample Parking, Big Fenced Yard, First and Second Floor Covered Balconies, 110' waterfront with 80' Dock, 5 Minute Walk to Beach, 10 Minutes to ValHala Sand Bar, on a 200' Wide Canal. Licensed to sleep up to 12 guests; 5 King Beds, 1 Pullout Sofa Bed. Outdoor 4 lounge chairs, 12 adirondack chairs, 2 outdoor tables with seating for 8. Fully stocked kitchen. License No. VACA-22-157

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, 106 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.

An aerial view displays a spacious, upscale home surrounded by lush greenery and water. The teal roof contrasts against the natural landscape, while the clear waters of Florida Bay extend into the horizon, showcasing shades of blue and green.

4.97 out of 5 average rating, 39 reviews

Ocean Dream

Ocean Dream.... a bright beautiful upscale home with fantastic ocean views over Florida Bay. Watch sunsets and sunrises from either balcony and the new observation platform extending 60 feet into the water. Experience nature at its finest from your 140 foot ocean frontage estate or go further afield on the included kayaks and SUPs. Beautiful gardens, outdoor living area, new pool and spa*, ping pong and bocce, all included in your week of paradise. License VACA 23-380

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.

4.88 out of 5 average rating, 82 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, 56 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.

4.82 out of 5 average rating, 104 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, 132 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