Mansion holiday rentals in Florida Keys

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!

Mariners Club Resort, Best in the Upper Keys

SPACIOUS AND STUNNING Family Friendly 4+ br home. One of the few to allow 10 guests! POOLS w/ hot tubs MARINA for direct access to reef; diving, snorkeling, fishing & sandbars KAYAKING Pennekemp DISCOUNT to swim with dolphins at DPMMR ACTIVITIES; tennis & pickleball courts, gym & game room. LOCATION: restaurants, bars, grocery and other conveniences PARKING for two cars on site WE ARE LOCALS who know the importance of family time so look no further than this special slice of paradise!

Pet Friendly Half Duplex Pool Home with Boat Slip

Want a spacious home with private pool and dock? You have found it! On a deep water canal. Enough dock space for a 37' boat. Enjoy your private heated pool or lounge in the shade or sun Easy walking to restaurants, shops, golf course, park, playground and entertainment. YOU MUST AGREE TO THE CITY'S RULES, IF YOU BOOK. Pool heater optional. $50/night or $250/week Any reservation starting after 6/13/23 will NOT include access to the Cabana Club but that will be available for a daily fee.

Horizon

Horizon is a bright beautiful upscale home, custom designed to take full advantage of its unique ocean location. Every room, has a wide sliding glass door to oceanfront balconies. Every bedroom has a private bath. Pool with Spa, Observation Platform for those sunrises on open water, ping pong, corn toss, kayaks and paddle boards, multiple dining areas, WIFI, quality appliances, comfy cotton bedding, crib, high chair multiple TV's poolside loungers, rocking chairs & bird watching. ++++

Family Tigertail Beach Home -Completely Remodeled!

Our Tigertail Beach house has been completely remodeled. Completely remodeled inside and out to mid-modern beach décor. Located in a very quiet and private neighborhood yet only a short walk to Tigertail Beach. Close to several restaurants, grocery stores, shopping, and much more! The house offers 4 bedrooms and 3 full bathrooms. 3 King Beds, 1 Queen Sofa-Sleeper, 2 Twin Bunk Beds, and a Pack n' Play if needed. Perfect house for your family beach getaway! Our reviews speak for themselves!

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.

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.

Lux Comfortable Home Sun On The Lanai All Day

Welcome to your perfect island getaway! This stunning 4-bedroom, 3-bath custom home is impeccably maintained, spotlessly clean, and beautifully furnished for ultimate comfort. Enjoy spacious living areas, a well-stocked kitchen, and two king suites with en suite baths. Open the glass wall to lounge outdoors, dine al fresco, or soak up the sun on the cantilever canal dock. Relax by the heated pool under the lanai and take in serene waterfront views—your dream escape awaits!

Seaside Luxury Escape with Pool, Dock & Kayaks

Paradise Point – Oceanfront Elegance in Marathon, FL 4 Bedrooms • 3 Bathrooms • Pool & Spa • Outdoor Kitchen • 90-ft Dock Welcome to Paradise Point, an oceanfront retreat where modern coastal design meets relaxed Keys living. This stunning 4-bedroom, 3-bathroom home offers sweeping open-water views, resort-style amenities, and everything you need for a luxury stay in Marathon. For larger groups, inquire about renting our neighboring 4-bedroom home for additional space.

Casa Cascada in Coral Gables Area

Welcome to Casa Cascada - in the heart of Coral Gables. Where you are 3 miles from Miami International Airport, close to Miracle Mile, Little Havana, South Beach and some of the best restaurants and shopping in Miami. Come and stay a while where the vibe is eclectic and inspiring, yet the most relaxing. Enjoy any one of our four open concept bedrooms — or relax in our personal favorite space, the backyard. Where the sound of the waterfall soothes your soul.

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.

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