Villas and Holiday homes in Florida Keys

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Florida Keys holiday homes
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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

Coral Villa By Avantstay| Close 2 Dt Key West! - Florida Keys
9.0 2 reviews

Coral Villa By Avantstay| Close 2 Dt Key West!

house, Stock Island
This Stock Island townhome is located in a quiet, gated community, offering proximity to Duval Street, Smathers Beach, and the airport, approximately 4 kilometres from Key West Golf Course.
This property sleeps 8 and features 3 bedrooms, 3 bathrooms, air conditioning, a swimming pool, garden, parking for two vehicles, and a kitchen with a fridge, freezer, and dishwasher, ideal for a Key West holiday.
Waterfront Luxury Villa 21 With Sunset Views And Boat Slip - Florida Keys
9.9 57 reviews

Waterfront Luxury Villa 21 With Sunset Views And Boat Slip

house, Marathon
This townhouse is located in Marathon, just 800 metres from the Florida Keys Aquarium Encounters and a short drive from other popular attractions like Captain Hook's Marina Dive Center and the Seven Mile Bridge. The property has received excellent ratings for location, cleanliness and user experience.
The property offers a fully equipped kitchen with a dishwasher and oven, a washing machine, free Wi-Fi, a balcony, free parking, and a swimming pool. Guests can enjoy sea views, relax in the garden, and take advantage of the nearby cycling and diving opportunities.
Tropical 2br2ba Getaway In Gorgeous Key Largo, Marina, Saltwater Lagoon, Pool - Florida Keys
10 3 reviews

Tropical 2br2ba Getaway In Gorgeous Key Largo, Marina, Saltwater Lagoon, Pool

house, Key Largo
This beachfront Key Largo property offers direct access to a marina and saltwater lagoon, situated along the coast for an ideal waterside getaway.
This 85 square meter villa accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a swimming pool, a terrace, garden, tennis court, barbecue facilities, and Wi-Fi.
Waterfront Townhouse In Kawama - Florida Keys
9.8 168 reviews

Waterfront Townhouse In Kawama

apartment, Key Largo
This waterfront property in Key Largo is within easy reach of Baker's Cay Resort Beach, Jimmy Johnson's Big Chill, and other popular attractions. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom house spans 89 square metres and comfortably accommodates up to six guests. The property offers a range of amenities including a private pool, garden, barbecue grills, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.

Best Florida Keys villas and holiday homes with a kitchen

Belari Oasis - Florida Keys
No reviews

Belari Oasis

house, Kendale Lakes
Belari Oasis is located in Kendale Lakes, a district approximately 15.9 kilometres from Miami International Airport.
This spacious one-bedroom villa, accommodating up to 27 guests, features a fully equipped kitchen with modern appliances, air conditioning, complimentary WiFi, private parking, and a private swimming pool with a terrace, all spread across 344 square meters.
Charming House With Private Pool N Coral Gable - Florida Keys
9.0 5 reviews

Charming House With Private Pool N Coral Gable

house, Glenvar Heights
This four-bedroom house is situated in Coral Gables, Miami, just 6.7 kilometres from the Cocowalk Shopping Center and 11.6 kilometres from the Vizcaya Museum.
The 191 square metre property features a private swimming pool, a fully equipped kitchen and a garden, comfortably accommodating up to 19 guests.
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly - Florida Keys
9.9 16 reviews

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly

house, Key West
This Key West holiday home is situated 1.8 kilometres from Duval Street and the Ernest Hemingway Home and Museum.
The 121-square-metre property boasts a spacious layout with two bedrooms, two bathrooms, and a private patio offering sea views, accommodating up to 11 guests and including free bicycle use, a swimming pool, and free Wi-Fi.
B105 Moon Bay - Florida Keys
10 1 review

B105 Moon Bay

house, Key Largo
B-105 Moon Bay apartment in Key Largo is situated 3.5km from John Pennekamp Coral Reef State Park, offering easy access to other Florida Keys attractions such as Pigeon Key (16km) and Windley Key (31km).
This three-bedroom, two-bathroom dwelling sleeps fifteen guests and boasts a fully equipped kitchen with dishwasher, air conditioning, a swimming pool, free Wi-Fi, and private entrance; towels and linen are provided.

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

Cozy Home On The Water W Dock And Near Sandbar! - Florida Keys
No reviews

Cozy Home On The Water W Dock And Near Sandbar!

house, Tavernier
This Tavernier holiday home, near Harry Harris Park Beach (1.9 km), Pigeon Key (5 km), and Windley Key (13.4 km), offers waterfront access with a private dock.
The one-bedroom, two-bathroom property sleeps eight guests and features a fully equipped kitchen, washing machine, electric vehicle charging point, free Wi-Fi, and a private garden.
Indigo Reef #50 ~ The Palms, Sunset Views & 31' Boat Slip - Florida Keys
9.6 5 reviews

Indigo Reef #50 ~ The Palms, Sunset Views & 31' Boat Slip

apartment, Marathon
This property is situated in the Indigo Reef Marina Resort in Marathon, Florida Keys, offering stunning open Gulf views and easy access to Vaca Cut for ocean access. The house has received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom property spans 149 square metres and comfortably accommodates six guests. Guests can enjoy a range of amenities, including a private swimming pool, a spa, a fitness centre, and a terrace with breathtaking Gulf views.
Unwind On Your Oceanedge Villa On Seapalm Island - Florida Keys
9.6 43 reviews

Unwind On Your Oceanedge Villa On Seapalm Island

house, Duck Key
This Duck Key villa, near Little Conch Key and Walkers Island, is conveniently located 4.8 kilometres from Curry Hammock State Park.
This five-bedroom, six-bathroom property boasts 446 square metres of living space, a private pool, and can comfortably accommodate up to twelve guests, offering free Wi-Fi and access to onsite amenities including a playground and barbecue grills.
Villa Castillo | Luxury Pool Home & Bbq | Redland. - Florida Keys
10 10 reviews

Villa Castillo | Luxury Pool Home & Bbq | Redland.

house, Princeton
This detached house, located in Miami's Redland district, offers a private one-acre setting with exceptional seclusion.
This family-friendly residence accommodates up to 12 guests and features a swimming pool, jacuzzi, outdoor kitchen, and a pool table for entertainment.

Best Florida Keys villas and holiday homes with jacuzzi

Heavenly Hideaway Ocean Pointe 3306 - Florida Keys
10 1 review

Heavenly Hideaway Ocean Pointe 3306

house, Tavernier
Heavenly Hideaway Ocean Pointe 3306, a two-bedroom house in Tavernier, Florida, offers ocean views and is a short walk (less than 2km) from Harry Harris Park Beach, with Pigeon Key (4.5km), Windley Key Fossil Reef Geological State Park (14.3km), and John Pennekamp Coral Reef State Park (17.7km) also within easy reach.
This 80 square metre property sleeps eight guests and boasts a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, parking, and in-unit laundry facilities; perfect for a self-catering holiday.
Marina To Ocean View Key Largo Ocean Pointe 5308 - Florida Keys
9.9 7 reviews

Marina To Ocean View Key Largo Ocean Pointe 5308

house, Tavernier
This Tavernier holiday home, Ocean Pointe 5308 in Key Largo, is situated near Harry Harris Park Beach (a 15-minute walk away) and within 18km of John Pennekamp Coral Reef State Park and Windley Key.
The 77-square-metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a swimming pool, jacuzzi, and fully equipped kitchen with dishwasher; free Wi-Fi and cable TV are also provided.
2405 Ocean Pointe Suites - Florida Keys
9.7 3 reviews

2405 Ocean Pointe Suites

house, Tavernier
Ocean Pointe Suites in Tavernier offers a self-catering apartment, conveniently located 19.3km from Upper Matecumbe Key, 14.6km from Windley Key Fossil Reef, and 5km from Pigeon Key, providing easy access to Tavernier's key attractions.
This 79 square metre, two-bedroom, two-bathroom flat sleeps up to 11 guests and boasts a fully equipped kitchen, swimming pool, Jacuzzi, free Wi-Fi, and air conditioning; Harry Harris Park Beach is a short 13-minute walk away.
Starfish Seas Key Largo Ocean Pointe 1302 - Florida Keys
9.8 25 reviews

Starfish Seas Key Largo Ocean Pointe 1302

house, Tavernier
Starfish Seas Key Largo Ocean Pointe 1302, located in Key Largo, offers ocean views and is a 2km walk from Harry Harris Park Beach, with easy access to Pigeon Key (5.1km), Windley Key Fossil Reef Geological State Park (15km), and John Pennekamp Coral Reef State Park (18km).
This 77 square metre, two-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen, swimming pool, jacuzzi, garden, parking, air conditioning, Wi-Fi, and cable TV.
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