
Luxury rentals in Florida Keys
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Top-rated luxury holiday rentals in Florida Keys
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New Waterfront Luxe: Pool-Spa-Dock-Beach-Gulf View
The Gulfside Retreat is the perfect tropical luxury location to unwind in the sun, enjoy endless activities, and stay a while. This 4-bedroom, 5-bathroom 1.5 acre Gulf-front home offers the ideal private resort experience. Our home features an open layout with massive outdoor space and amazing Gulf views. You will have your own private beach, boat dockage, protected lagoon, and a long private pier to enjoy the gulf breezes. Plus, easy access to the oceanside in minutes by boat via the Vaca Cut.

Oceanfront Mangrove Manor at SeaGlass Cove FL Keys
Mangrove Manor at SeaGlass Cove is a luxury oceanfront retreat in Marathon, Florida. This modern five-bedroom home features panoramic Atlantic views, refined coastal interiors, and seamless indoor-outdoor living. Sleeps twelve with a chef’s kitchen, ocean-view terrace, and access to resort-style amenities including a pool and pickleball courts. Located near marinas, dining, boating, fishing, and snorkeling, with concierge services for charters and private chefs. Perfect for relaxed Keys escapes.

Dolce Vita Estate • Luxury Private Villa • Events
⚜️Welcome to Dolce Vita Estate, a private 5-acre retreat where laid-back luxury meets effortless charm. The space includes a heated pool, 5 beautifully designed bedrooms, a chef’s kitchen, and 3 gardens for reflection, celebration and meditation with serene views in every direction. This is where time slows down. Ideal for intimate escapes or special moments worth celebrating. Step away from the noise and gather with loved ones. Not just a place to stay but a place to experience the Dolce Vita

Satori | Luxury Villa in Miami with Heated Pool
Satori is a light-filled retreat in the heart of Miami’s Design District created for guests who value design and elevated living. Defined by soaring ceilings and expansive windows, the residence is intentionally curated to blend Contemporary Modern with Miami Minimalism. The home includes 5 spacious bedrooms, each with its own en-suite bathroom, ensuring comfort, discretion, and an unforgettable experience for 12 guests. Ideally situated to explore vibrant attractions and activities in Miami.

1 Hotel - Direct Ocean View 1 Bedroom/1 Bath Suite
This south-facing 1-bedroom suite is the closest to the ocean, with the best views in the building of all comparable suites. Enjoy breathtaking views of the ocean and the hotel's stunning pool deck from your private balcony. During your stay at the 1 Hotel you will have full access to all of the building's top-notch amenities, private beach, beach club, many dining options and multiple pools, including the rooftop pool. All of this in the heart of South Beach with all Miami has to offer!

Peninsula Villa | Boat Dock | Heated Pool | Sunset
This grand peninsula retreat, embraced by the Ocean and lush mangroves offering utmost privacy, has been designed for ultimate vacationing. Nestled along the tranquil shores of Florida Bay, its array of indoor & outdoor living and lounge areas, heated pool with a tiki bar, expansive sandy playgrounds, dock with ocean-access canal, gazebo boasting sunset views make this magical oasis ideal for serene escapes or vibrant family gatherings. Enhanced cleaning practices implemented.

2-Story 3BD Brickell Penthouse | Heated Pool | Gym
This incredible penthouse offers the premium amenities and service of a luxury hotel, combined with the space and value of a vacation rental. Enjoy sweeping views of Brickell and Biscayne Bay from the top 2 floors of the building. The first floor has floor-to-ceiling windows, flooding the space with natural light, along with a balcony and the 1st bedroom. The second floor has 2 bedrooms as well as a dedicated work space. The property is located in the heart of Brickell.

Maya's Secret Treasure at Duval - Unique Condo
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. ** Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West.

4 Bedroom Oceanview Villa – Capacity 8
Enjoy abundant space with spectacular Atlantic Ocean views, and embrace the surrounding natural haven with indoor-outdoor living. At 3,100 SF each, the Villas include 3 in-suite king-bed bedrooms and 1 twin room, a full kitchen, dining room, laundry room, waterfront balconies, a 2-car garage. Please note Airbnb does not collect 5% tourism tax. This tourism tax will be charged on property at the time of check in with the credit card you provide when you arrive

Miami Jungle Retreat | Luxury Wellness Oasis
Welcome to Jungle Book House, a one-of-a-kind luxury wellness retreat just 5 minutes from Downtown Miami. Surrounded by lush gardens, century-old trees, and modern tropical design, this home is made for relaxation and reconnection. Enjoy a steam shower, open living spaces, and a stone Caribbean bench under the stars. Whether for a mindful getaway, romantic escape, or stylish city stay, Jungle Book offers serenity steps from Miami’s vibrant heart.

Evershore Estate at Lunara Bay | Wellness Home
Evershore Estate is a waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community. Perfect for activity and relaxation, it features a private pool and dock, parking, a pet-friendly gated yard, and fitness amenities including a Peloton, free weights, and yoga mats. Tailored itineraries help you uncover hidden gems and local favorites for an unforgettable Lunara Bay experience.

Oceanview Private Penthouse at The Setai - 3803
Experience the sophistication of this private residence at The Setai, Miami Beach. With two bedrooms, a den with a full-size sofa bed, three bathrooms, and a modern kitchen, it’s ideal for families or couples. Enjoy ocean views from your balcony, unwind at the Valmont Spa, or relax by one of three pools. Perfectly located in South Beach, it offers both vibrant energy and serene relaxation.
Popular amenities for Florida Keys luxury holiday rentals
Other great luxury holiday rentals in Florida Keys

Stunning Private Residence at W South Beach - 804

House of the Royal Palms in Old Town
Oceanview Private Residence at The Setai -2401

Private Beach, Pickleball Court and Tiki Bar

Oceanfront + Resort Perks | 4BR Villa (Sleeps 8)

Oceanview 4BR Family Villa + Resort Perks | Bunks

Oceanview Private Condo at 1 Hotel & Homes -1144

Oceanfront Private Condo at 1 Hotel & Homes -1120
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
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- Orlando Holiday rentals
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- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Everglades National Park
- University of Miami
- Sombrero Beach
- LoanDepot Park
- Dolphin Mall
- Zoo Miami
- Calle Ocho Plaza
- John Pennekamp Coral Reef State Park
- CG Cosmetic Surgery
- Biscayne National Park
- Crandon Beach
- Key Biscayne Beach
- Florida International University
- Biltmore Golf Course Miami
- Avana Plastic Surgery
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Mia Aesthetics Miami
- Fairchild Tropical Botanic Garden
- Dadeland Mall
- Things to do Florida Keys
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- Things to do United States
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