Mansion vacation rentals in Key West

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.

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!

Casa Rosa: 4BR/4BA house, pool, near Duval

Casa Rosa, a historic eyebrow home in Key West, offers 4 bedrooms, 4 bathrooms, a private pool, hot tub, and prime location just a block from Duval Street. Enjoy charming décor, a fully equipped kitchen, and outdoor dining surrounded by tropical foliage. Relax in the serene backyard oasis or explore nearby attractions like the Hemingway Home, Mallory Square, and Southernmost Point. Pool heat available for $250+ tax per week. Book now for an unforgettable stay! Saturday-to-Saturday Rentals Only.

Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.

Experience the beauty of the Florida Keys from this stunning open-water waterfront home in Marathon. This spacious 4-bedroom, 3.5-bath retreat offers breathtaking sunset views and endless ocean vistas. The two-story open layout is designed for families and friends, providing generous gathering spaces while maintaining privacy. Arriving by boat? Enjoy the convenience of a 70-foot private dock with a freshwater hose for boat rinsing and engine flushing. Check in and Check out only Saturday.

Endless Summer at Old Town

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** All year long you dream of a getaway to capture that feeling of Key West's endless summer - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with

Luxury Waterfront Home - Marathon, FL Keys - 5BR

Welcome to Seven Sunsets – a waterfront retreat in Marathon’s brand-new Emerald Flats community, offering stunning ocean views and the iconic Seven Mile Bridge. With glowing sunset backdrops, marina views, and dockage for up to a 40’ boat, this five-bedroom home is perfect for families, boaters, and sunset lovers. Enjoy a small beach area with paddle boards, spacious indoor-outdoor living, and amenities like a fully stocked kitchen, in-home laundry, outdoor games, and pet-friendly policies.

Marathon Villa w/ Priv Pool/Dock Sombrero Beach

Marathon, Florida is in the middle of all the beauty and action of what the Florida Keys have to offer. Sombrero Beach is at a bike ride or walking distance. It offers complimentary parking, outdoor grilling, beach volleyball, children play area, and public restrooms. 40 foot dock offers guests the option to bring their boats or rent one. Our heated pool is a perfect way to soak up the tropical vibes. Kitchen is fully equipped. We are at walking distance to grocery store!

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

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.

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.

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.

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