
Holiday rentals in Florida Keys
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Top-rated holiday rentals in Florida Keys
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Beach House, Private Pool, Dock, Gulf View Sunsets
You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Viamarhe House-Private beach, Kayak, yard games
If you are looking to enjoy the natural beauty and the captivating views of the Florida Keys, our charming Oceanfront house is the place for you. Enjoy the breathtaking views of the sunrise and the starry night show over the beautiful Atlantic ocean. You and your family can enjoy the exclusivity this property will give you, Viamarhe is its own little resort, 5 kayak and fishing rods, volleyball, chess and bowling ground, Domino, Billiards, Ping-Pong, and Football. the propane BBQ grill, fire pit

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!
✨ Welcome to Paradise Point! 🌊⛵ Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard🎣🐟 After a day on the water, unwind in your Heated Pool, take in the breathtaking views, & fire up the grill for a sunset BBQ to remember! 🌅 Whether you're looking for relaxation, luxury, or adventure, Paradise Point has it all! 🌴☀️

Paradise in the Keys
Welcome to Pura Vista otherwise known as Pure Views. Come enjoy a delightful stay at this beautiful direct waterfront property in the Florida Keys for your getaway. Breath taking views of the Atlantic Ocean and direct ocean access to the best boating activities in the warm turquoise waters of the Florida Keys. Well equipped with commodities to help your stay be the best. A great location to discover everything the Florida Keys has to offer. We look forward to hosting your stay! VACA – 22 - 376

Villa 5008 on Duck Key - Boat Slip Available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

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

b watervibe
Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

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.
Popular amenities for Florida Keys holiday rentals
Other great holiday rentals in Florida Keys

Florida Keys Oceanside Utopia

Dock, Beach Club, Ocean & Gulf Access, Tennis

Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool

Oceanfront mermaid house pool and dock

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Castillo Del Mar- Ocean access from your backyard

Honeymoon Harbor

Grand Arenas/ 120'Dock/ Mini Golf/ HtPool / GRoom
Frequently Asked Questions
Where is Florida Keys located?
Florida Keys is a chain of islands stretching off the southern tip of Florida, surrounded by the Atlantic Ocean and Gulf of Mexico. The area is known for tropical scenery, marine life, and distinct communities rooted in maritime traditions.
When is the best time to visit Florida Keys?
Visitors often favor late winter and spring for milder temperatures around 66–81°F (19–27°C) and lighter rainfall. Summer months can be warmer, reaching near 91°F (33°C), with more frequent showers, but activities continue year-round.
What are some things to do near Florida Keys?
You can explore local coral reefs by snorkeling or diving, visit historic sites in Key West, and enjoy kayaking or fishing around the islands. The region also has public beaches, galleries, and culinary experiences shaped by coastal influences.
How is the weather near Florida Keys?
Florida Keys has a subtropical climate, with winter temperatures near 61–76°F (16–25°C) and warmer summers reaching 78–91°F (25–33°C). Rain is more frequent from May to October, so light clothing and sun protection are recommended throughout the year.
Destinations to explore
- Seminole Holiday rentals
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- Miami Beach Holiday rentals
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- Bed and breakfasts Florida Keys
- Guest house rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Boat rentals Florida Keys
- Private suite rentals Florida Keys
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- Rentals with an accessible-height toilet Florida Keys
- Campsite rentals Florida Keys
- Beach apartment rentals Florida Keys
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- Apartment rentals Florida Keys
- Rentals with lake access Florida Keys
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- Rentals with a hot tub Florida Keys
- Rentals with a kayak Florida Keys
- Luxury rentals Florida Keys
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- Waterfront rentals Florida Keys
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- Rentals with an accessible-height bed Florida Keys
- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Everglades National Park
- University of Miami
- Calle Ocho Plaza
- Sombrero Beach
- LoanDepot Park
- Dolphin Mall
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Florida International University
- Key Biscayne Beach
- Biscayne National Park
- CG Cosmetic Surgery
- Crandon Beach
- Biltmore Golf Course Miami
- Avana Plastic Surgery
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Fairchild Tropical Botanic Garden
- Schnebly Redland's Winery & Brewery
- Sea Oats Beach
- Things to do Florida Keys
- Food and drink Florida Keys
- Sports activities Florida Keys
- Sightseeing Florida Keys
- Art and culture Florida Keys
- Tours Florida Keys
- Nature and outdoors Florida Keys
- Things to do Florida
- Sports activities Florida
- Art and culture Florida
- Nature and outdoors Florida
- Entertainment Florida
- Food and drink Florida
- Tours Florida
- Sightseeing Florida
- Wellness Florida
- Things to do United States
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