Mansion holiday rentals in Key West

2 Pools, Beach, Pickleball, Coffee Bar, Food Truck

“Vacay Vibes” A Trendy & Modern 4/4 Home in Key Largo…just steps to the largest pool in the Florida Keys! Sandy beach with ocean views. Food Truck, Indoor/outdoor Pickleball, Tennis, and Basketball. Game room, Fitness center, on-site Marina, and 2 Jacuzzis. Comfortable beds, en-suite baths, a screened-in backyard lounge, and a fun LED photo wall await you. Fully stocked kitchen, coffee bar, stair-free entry with kitchenette, and in-unit laundry. Licensed, Top 1% Home, Guest Favorite & SuperHost!

Luxury Beachside Retreat - Modern 5BR/5BA w/ Pool

Modern 3,700+ sq. ft. home built in 2022, steps from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles, and all toiletries/paper products provided. Spacious, pet-friendly, and perfect for families or groups. Enjoy breathtaking views and hotel-like amenities. Book your dream vacation today! Inquire for off season specials or for longer stay discounts! 12 person max

Islamorada Cay Home. Elegant home

Stunning Islamorad Home off Tavernier Creek. Spacious home. Enjoy your privacy of your own pool. Large pool & paved deck. Fishermen bring your large boat. 100ft dock space w/30 amp. An elegant 4 bedroom, 3 bath resort like feel when you arrive. Small private beach. Game room. Master bedroom en suite. Private gated home. 1 dog under 30lbs. If using pool heater in the winter you pay for the propane with what you use. Boating access truly mins to ocean & bay. & fuel.Guest love this Coastal home

Oceanview Luxury Retreat 12 Guest 6 Beds Pool&Dock

Enjoy Ocean views and stay in luxury at this brand new five bedroom four bathroom Marathon masterpiece including a pool and 40 feet of dockage overlooking the Atlantic Ocean. The spacious kitchen, cocktail lounge and living area with a giant TV make for a wonderful relaxing stay. Five bedrooms and four full bathrooms will accommodate large groups. Upstairs find two master suites and a third suite with direct bathroom access. Unique pool has both sun and shade with optional pool heat for a fee.

Key Colony Beach-POOL & DOCK

Escape to a 4-bed, 1800 sq. ft. waterfront haven! On a deep canal opening to Vaca cut this gem offers all you need. The master suite boasts a king bed, there are three queen beds in separate rooms. Dive into the pool or to the private dock for waterway access. Upstairs, an open kitchen with a six-person breakfast bar beckons culinary adventures. Downstairs, an outdoor kitchen invites alfresco delights. This non-smoking sanctuary is more than a rental—it's a canvas for unforgettable moments.

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Snapper House: New lux vacation home with 4 master

Snapper House has everything and more for an unforgettable vacation: 4 master suites with exclusive bathrooms and coffee/wine bars, specialty purple mattresses and luxury linens, a great room for entertaining and gracious living, powder room, laundry, elevator, expansive wrap around deck, pool, pool bathroom, bait freezer, icemaker, gear storage, and long dock. Just completed in March 2020 in the exclusive Key Colony Beach community. Part of the HappyintheKeys collection.

Anglers Terrace, Condé 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

Bayfront Home with Heated Pool.

NEW TO MARKET! This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool is surrounded by Turkish marble pavers that are cool to your feet. House has double master suites with en suite bathrooms and every necessity to make our home feel like yours.