Villas and Holiday homes in Florida Keys

4979 available villa offers

-
7
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Florida Keys holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

4979 Villa rentals in Florida Keys

Best Florida Keys villas and holiday homes with a pool

Among the 4979 accommodations in Florida Keys, here are the 4 best villas and holiday homes with a pool

Bayside Townhome In Islamorada With Boat Slip - Florida Keys
10 89 reviews

Bayside Townhome In Islamorada With Boat Slip

house, Islamorada, Village of Islands
This luxurious yacht is situated in the Futura Yacht Club gated community in Islamorada, just a short distance from restaurants, shops, and the famous Islamorada sandbar. The property has received excellent ratings for location, cleanliness, and user experience.
This spacious yacht offers two bedrooms and two bathrooms, comfortably accommodating up to four guests. The yacht boasts a range of amenities including a private beach area, a swimming pool, a fitness centre, and a kitchen with modern appliances.
Starfish Cottage - Summer Fun.  Sleeps 4 -Boating Fishing And Lobster  Season. - Florida Keys
9.8 64 reviews

Starfish Cottage - Summer Fun. Sleeps 4 -Boating Fishing And Lobster Season.

cottage, Cudjoe Key
The New Hidden Hammock Resort - Pink Cottage Unit #3, a seaside cottage in Cudjoe Key, Florida, is located less than 1.6km from Florida Keys Beaches and Crab Key, and within 9.6km of the Big Pine Key Flea Market and National Key Deer Refuge Visitor Centre.
This 51-square-metre self-catering property features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and access to a swimming pool and garden.
Waterfront 2br, 2ba Islamorada Retreat With Pool, Hot Tub, And Kayaks. - Florida Keys
No reviews

Waterfront 2br, 2ba Islamorada Retreat With Pool, Hot Tub, And Kayaks.

house, Islamorada, Village of Islands
This pet-friendly villa in Islamorada's Seabreeze Trailer Park offers a prime waterfront position, situated 724 metres from Islamorada County Park and 884 metres from Founders Park, with convenient access to water sports and local eateries such as Hog Heaven.
This three-bedroom, two-bathroom holiday home accommodates up to six guests and features air conditioning, complimentary Wi-Fi, a fully equipped kitchen, a shared swimming pool, hot tub, and a balcony, ensuring a comfortable stay with on-site leisure facilities.
Ocean Side Paradise Awaits - Florida Keys
9.3 4 reviews

Ocean Side Paradise Awaits

house, Marathon
Ocean Side Paradise Awaits, a self-catering property in Marathon, Florida, is located an 1.8 km walk from the Florida Keys Aquarium Encounters, and close to Captain Hook's Marina Dive Centre and A Deep Blue Dive Centre.
This 850 square metre house features one bedroom, two bathrooms, and can accommodate four guests, offering a swimming pool, terrace, air conditioning, free Wi-Fi, and a fully equipped kitchen with a fridge and microwave.

Best Florida Keys villas and holiday homes with a kitchen

Charming Cottages, Dockage, Pool, Just Minutes To Key West - Florida Keys
8.6 133 reviews

Charming Cottages, Dockage, Pool, Just Minutes To Key West

cottage, Cudjoe Key
This Summerland Key holiday home is situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to these nearby islands.
The 73 square metre property sleeps four guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, washing machine, barbecue, swimming pool, and parking, plus Wi-Fi access.
Ma132 Hook, Line & Sunset - Florida Keys
No reviews

Ma132 Hook, Line & Sunset

house, Marathon
This waterfront cottage in Marathon is located 46 kilometres from Upper Matecumbe Key and 9.6 kilometres from the Seven Mile Bridge, with Florida Keys Aquarium Encounters and several dive centres nearby.
This property offers 96 square metres of living space, accommodating up to 11 guests with one bedroom, two bathrooms, a fully equipped kitchen including a fridge and microwave, free WiFi, three televisions, and an in-unit washer and dryer.
Cottage With Pool  And Boat Dockage Just Minutes To Key West! - Florida Keys
8.6 168 reviews

Cottage With Pool And Boat Dockage Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key waterfront cottage, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning views and direct water access.
The 36 square metre property sleeps two in one bedroom, one bathroom, and boasts a fully equipped kitchen, private terrace, swimming pool, garden, and barbecue facilities.
Canal Front, Dockage, 2 Bedroom,  2 Bath - Florida Keys
8.8 106 reviews

Canal Front, Dockage, 2 Bedroom, 2 Bath

cottage, Cudjoe Key
This charming waterfront cottage is situated on Cudjoe Key, just a short walk from Venture Key and a 6-mile drive from Upper Sugarloaf Key and Florida Keys Beaches, offering a peaceful escape in a beautiful location. It has been rated excellent by previous guests.
The cottage has two bedrooms and two bathrooms, making it suitable for a family or group of four. Guests can enjoy a range of amenities, including a private pool, barbecue grills, a fully equipped kitchen, and a washing machine, as well as a patio for relaxing and a TV for entertainment.

Frequently asked questions about villa rentals in Florida Keys

  • What are the must-see attractions in the Florida Keys?

    The Florida Keys offer a plethora of attractions. For natural beauty, you absolutely must visit Dry Tortugas National Park, accessible by boat or seaplane, for its stunning coral reefs and historic fort. Key West is a must-see, with its iconic Southernmost Point Buoy, Ernest Hemingway Home and Museum, and Mallory Square for the sunset celebration. Further up the Keys, Bahia Honda State Park boasts beautiful beaches and a historic bridge, perfect for swimming and relaxing. The Seven Mile Bridge is an architectural marvel and offers incredible views.
  • What are the best holiday homes in Florida Keys?

  • Is the Florida Keys known for mountains, beaches, forests, or other types of landscapes?

    The Florida Keys are known primarily for their stunning beaches, coral reefs, and the unique landscape of low-lying islands. Think turquoise waters, mangrove forests, and a sub-tropical climate. Mountains are absent; the terrain is very flat.
  • What are the best holiday homes with a pool in Florida Keys?

  • What are some surprising and hidden attractions in the Florida Keys?

    Many find the less-visited areas of the Keys surprisingly charming. The John Pennekamp Coral Reef State Park offers incredible snorkelling and diving opportunities beyond the usual tourist hotspots. Exploring the backcountry roads reveals hidden coves and secluded beaches. For a unique experience, consider visiting the African Queen, a vintage steamboat featured in a famous film, located in Key Largo.
  • What are the best holiday homes with a jacuzzi in Florida Keys?

  • What are some unique ways to learn about the culture of the Florida Keys by engaging with its people?

    To truly experience the Keys' culture, engage with the local artists at galleries in Key West, Islamorada, and Marathon. Attend a local event like a Conch Republic Independence Celebration in Key West or a festival celebrating local seafood. Chat with the staff at smaller, family-run businesses; they often have fascinating stories to share about the Keys' history and way of life.
  • What are the best holiday homes for families and kids in Florida Keys?

  • How much time should you set aside to thoroughly explore the Florida Keys?

    A week allows for a good exploration of the Keys, enabling you to visit Key Largo, Islamorada, Marathon, and Key West, with time for activities. To truly appreciate the slower pace and explore more deeply, two weeks would be ideal. A shorter trip will necessarily focus on fewer areas.
  • What are the best pet friendly holiday homes in Florida Keys?

  • Is there anything you might not think to pack for the Florida Keys?

    Beyond the usual swimwear and sunscreen, remember reef-safe sunscreen to protect the delicate coral. Pack light clothing suitable for warm, humid weather, but also a light jacket or sweater for cooler evenings. Good walking shoes are essential for exploring, and don't forget insect repellent, especially for the mangrove areas.
  • What are the best holiday homes with parking in Florida Keys?

  • What cultural experiences or workshops in the Florida Keys offer something different?

    The Florida Keys offer various unique workshops. You could try a conch shell crafting workshop, learning traditional techniques. Several locations offer glassblowing or jewellery-making workshops using local materials. Check local listings for specific offerings during your visit.
  • Are there any food festivals in the Florida Keys where you can try local food?

    While specific dates vary annually, the Florida Keys host several events showcasing local cuisine. Key West's annual Conch Republic Independence Celebration often features food stalls with local dishes. Many restaurants across the Keys hold special events and festivals throughout the year, so checking local listings closer to your visit date is recommended. Look out for events featuring fresh seafood, key lime pie, and other local specialties.

Nearby regions

Best Florida Keys villas and holiday homes with air conditioning

The Florida Keys Treehouse In Marathon, Fl - Florida Keys
9.3 73 reviews

The Florida Keys Treehouse In Marathon, Fl

house, Marathon
This Marathon treehouse, located in Florida, is 9.2 kilometres from the Florida Keys Aquarium Encounters and 38.6 kilometres from Upper Matecumbe Key.
The 9-square-metre property offers two bedrooms, a living room, two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, a swimming pool, and free bikes for exploring the area; BBQ facilities and a picnic area are also available.
Villa Paradise ~ Heated Pool ~ Game Room ~ Miami - Florida Keys
No reviews

Villa Paradise ~ Heated Pool ~ Game Room ~ Miami

house, Country Walk
This 3-bedroom, 2-bathroom villa, Villa Paradise, is located in a quiet, family-friendly district of southern Miami-Dade County, approximately 1.3 kilometres from Larry and Penny Thompson Memorial Park and 56 kilometres from Downtown Miami by car.
Offering accommodation for up to 12 guests, this detached property boasts a private, fenced garden with a swimming pool, BBQ, fire pit, and lounge seating, alongside an entertainment room featuring arcade machines and a pool table, all managed by a smart home system.
Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Florida Keys
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
This holiday home is situated in the Matecumbe district of Islamorada, a 3-minute walk from Islamorada Brewery & Distillery and an 11-minute walk from the History of Diving Museum.
Guests can enjoy a communal swimming pool and hot tub, with amenities including a kayak and bicycles provided for outdoor activities, alongside on-site parking and complimentary Wi-Fi.
Imagine In The Keys - Venture Out Unit 073 - Florida Keys
9.6 4 reviews

Imagine In The Keys - Venture Out Unit 073

cottage, Cudjoe Key
This Cudjoe Key waterfront holiday home, situated 3.9km from Florida Keys Beaches and 9.7km from Upper Sugarloaf Key and Upper Sugarloaf Sound, offers stunning water views and direct water access.
The 74 square metre property boasts two bedrooms, two bathrooms, a private patio, swimming pool, jacuzzi, and barbecue facilities, sleeping up to six guests.

Best Florida Keys villas and holiday homes with jacuzzi

Tranquility On The Top Floor - Ocean Pointe 2404 - Florida Keys
No reviews

Tranquility On The Top Floor - Ocean Pointe 2404

house, Tavernier
This holiday apartment is located in Tavernier, 104 kilometres from Miami International Airport and a 13-minute walk from Harry Harris Park Beach.
This one-bedroom, one-bathroom property offers a fully equipped kitchen, air conditioning, a swimming pool, a hot tub, and a private balcony, with a guest capacity of six and a floor area of 70 square metres.
New! 4-story Villa, Private Rooftop, Pool And Marina In Key Largo - Florida Keys
10 1 review

New! 4-story Villa, Private Rooftop, Pool And Marina In Key Largo

house, Key Largo
This Key Largo house, situated near John Pennekamp Coral Reef State Park and Florida Keys National Marine Sanctuary (exact distances unspecified), offers convenient access to Key Largo's attractions.
This 199 square metre (2140 square foot) property boasts one bedroom, four bathrooms, and comfortably accommodates fifteen guests, featuring a private pool, Jacuzzi, fully equipped kitchen, free Wi-Fi, and free private parking.
Kc17 Dream In The Keys - Florida Keys
10 1 review

Kc17 Dream In The Keys

house, Key Colony Beach
This waterfront property in Key Colony Beach is situated 500 metres from the town centre and a 12-minute walk from Sunset Park Beach, offering proximity to A Deep Blue Dive Center (2.6 kilometres) and Florida Keys Aquarium Encounters (3.7 kilometres).
This spacious 177 square metre holiday home accommodates up to 15 guests with 3 bedrooms and 3 bathrooms, featuring a private hot tub, a 35-foot dock, a balcony, a well-equipped kitchen with a dishwasher and microwave, and access to an exclusive Cabana Club with pool and beach facilities, as well as an on-site children's playground.
Brand New Oceanside Paradise Waterfront With Pool And Hot Tub - Florida Keys
10 1 review

Brand New Oceanside Paradise Waterfront With Pool And Hot Tub

house, Key Largo
This Key Largo oceanfront property is situated 1 kilometre from Pigeon Key, 13.5 kilometres from John Pennekamp Coral Reef State Park, and 16 kilometres from Windley Key, offering easy access to major attractions.
This 250 square metre house boasts three bedrooms, three bathrooms, sleeps up to 17 guests, and includes a private pool, Jacuzzi, and a fully equipped kitchen; water sports are available on-site.