Mansion vacation rentals in Key West

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, 82 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

4.95 out of 5 average rating, 155 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!

An outdoor dining area features a large table set for six, adorned with blue glassware and elegant dinnerware. A lantern and a fruit arrangement are placed at the center, with panoramic views of the ocean visible in the background, complemented by a breezy atmosphere.

5 out of 5 average rating, 26 reviews

World-Class Oceanfront Pool/Hottub Sunset Escape

Escape to Oceans Cay Villas—luxury oceanfront in the Florida Keys. Why you’ll love the Islander: ✨ Heated swimming pool + Relaxing HOT TUB! ✨ Fire pit with perfect sunset views ✨ Fishing, snorkeling, and swimming in your backyard ✨ Free kayaks, paddle boards, and bicycles ✨ Walk or ride to Seven Mile Bridge ✨ Walking distance to restaurants and attractions ✨NO SEAGRASS SMELLS! ✨ Ping pong table ✨ Private dock for your boat ✨ Stylish, modern villa design ✨ Breathtaking SUNRISE and SUNSET views

4.83 out of 5 average rating, 109 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 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.

5 out of 5 average rating, 20 reviews

Vaca Cut w/60' dock, 4br/4ba, 2 kitchens

Calling all boaters and anglers—your Keys getaway awaits! This fully renovated 4BR/4BA home just off Vaca Cut delivers rare ocean + bayside access, a 60’ dock with power, fish-cleaning station, BBQ and docking setup. Unwind on the two-story waterfront deck while watching dolphins and manatees, then reach world-class fishing in minutes. Two kitchens, two living rooms, and plenty of room for families, friends, or couples. Minutes from Sombrero Beach, restaurants and shopping.

4.89 out of 5 average rating, 90 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

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, 111 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. 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.

4.82 out of 5 average rating, 106 reviews

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 spacious rooftop terrace is sheltered by a vibrant blue sail shade, featuring comfortable seating arranged around a central table. Lush palm trees and a water view are visible in the background, while clear skies enhance the overall ambiance.

4.97 out of 5 average rating, 141 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, 108 reviews

A serene waterfront view is captured, featuring a clear blue sky and calm waters. A wooden pier extends into the water, flanked by smooth stones along the shore. Green chairs are positioned for relaxation, nestled among lush greenery and mangroves.

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!

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.

4.95 out of 5 average rating, 115 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.