Compare Vacation Rentals & Airbnb in Florida Keys

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Florida Keys vacation rentals
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15393 Rentals and Airbnb in Florida Keys

Best family friendly Florida Keys vacation rentals

Among the 15393 accommodations in Florida Keys, here are the 4 best family friendly rentals

Waterfront Islamorada Condo  Heated Pool, Marina & Deeded Boat Slip - Florida Keys
10 68 reviews

Waterfront Islamorada Condo Heated Pool, Marina & Deeded Boat Slip

apartment, Islamorada, Village of Islands
This Islamorada condominium is situated at mile marker 88.5, offering convenient access to Robbie's Marina and the Theater of the Sea, with Miami located 108 kilometres to the north.
This family-friendly apartment, measuring 88 square metres and accommodating up to six guests, features two bedrooms and two bathrooms, a fully equipped kitchen with granite countertops, a private balcony with pool views, direct access to a deeded boat slip (#49), and resort-style amenities including a heated swimming pool and pickleball courts.
Florida Keys Retreat /Game Room / Boat Parking - Florida Keys
9.6 56 reviews

Florida Keys Retreat /Game Room / Boat Parking

apartment, Marathon
This Marathon Airbnb, minutes from Sombrero Beach and within walking distance (approximately 0.8km) of local restaurants, shops, and the marina, offers a convenient location for exploring the Florida Keys.
The two-bedroom, two-bathroom house sleeps six, includes a dedicated games room with a Nintendo Switch and fishing rods, and allows parking for up to three vehicles plus a boat trailer (maximum 7.6m).
Villa Valbuena Azul Escape 2 Kings Key Largo Pickleball Tennis Pool Lagoon - Florida Keys
9.8 272 reviews

Villa Valbuena Azul Escape 2 Kings Key Largo Pickleball Tennis Pool Lagoon

apartment, Key Largo
This apartment is conveniently located in Key Largo, just a short drive from popular attractions like John Pennekamp State Park, Pigeon Key, and Windley Key. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home offers a comfortable and well-equipped space for your stay. Guests can enjoy a range of amenities, including a private beach, a swimming pool, tennis courts, and free bikes and kayaks for exploring the area.
Sombrero Sanctuary~ Pool, Pet Friendly, Near Beach - Florida Keys
10 4 reviews

Sombrero Sanctuary~ Pool, Pet Friendly, Near Beach

apartment, Marathon
This canal-front flat in Marathon is located mere metres from Sombrero Beach, offering a private fishing dock with power and water, a fish cleaning station, bait freezer, and commercial ice maker.
This pet-friendly apartment accommodates up to 10 guests with a heated swimming pool, a screened balcony with a large Smart TV, air conditioning, and two bicycles for exploring the local area, plus parking for 4-5 vehicles including trailer space.

Best Florida Keys vacation rentals with a pool

Among the 15393 accommodations in Florida Keys, here are the 4 best rentals with a pool

Ocean Side Paradise Awaits - Florida Keys
9.2 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.
Turtle Nest 1 Private Beach,pool, 2bed 2bath - Florida Keys
9.8 139 reviews

Turtle Nest 1 Private Beach,pool, 2bed 2bath

apartment, Tavernier
This Ocean Pointe Suites apartment in Key Largo, near Tavernier, boasts direct Atlantic Ocean access and is conveniently located close to Key Largo's water sports activities.
The two-bedroom, two-bathroom property sleeps six, offering a king-size bed, queen bed, and pull-out queen sofa, plus a fully equipped kitchen, private beach access, swimming pool, jacuzzi, and ample on-site amenities including tennis courts, a playground, and boat storage.
Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025 - Florida Keys
9.7 11 reviews

Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025

apartment, Key Largo
This Key Largo condo is conveniently located near a marina, 7.7km from John Pennekamp Coral Reef State Park and 9.3km from Pigeon Key.
The 12-square-metre apartment offers two bedrooms, two bathrooms, sleeps thirteen guests, and features a full kitchen, free Wi-Fi, a swimming pool, tennis court, and private parking; plus outdoor play equipment and an outdoor fireplace.
Luxury Condominium In Key Largo... Sunsets, Marina - Florida Keys
9.6 128 reviews

Luxury Condominium In Key Largo... Sunsets, Marina

apartment, Key Largo
This renovated fourth-floor flat in Key Largo's Kawama Yacht Club offers ocean views and is situated approximately 1.6 kilometres from John Pennekamp Coral Reef State Park and 2.4 kilometres from Dagny Johnson Key Largo Hammock Botanical State Park.
This 111 square metre, two-bedroom, two-bathroom apartment accommodates up to eight guests and features a modern kitchen, air conditioning, a swimming pool, and complimentary boat ramp access.

Frequently Asked Questions about vacation rentals in Florida Keys

  • What are the must-see sights in the Florida Keys, United States?

    The Florida Keys offer a plethora of sights. Key West is a must, with its iconic Southernmost Point Buoy, Ernest Hemingway Home and Museum, and the Key West Butterfly and Nature Conservatory. Further up the Keys, you'll find the Seven Mile Bridge, a breathtaking engineering marvel, and Bahia Honda State Park, boasting pristine beaches and excellent snorkeling. Don't miss the John Pennekamp Coral Reef State Park, a great place for diving and exploring the only living coral reef in the continental United States.
  • What are the best Airbnb and vacation rentals in Florida Keys?

  • What are vacation rentals like in Florida?

    There is a wide range of vacation rentals available in Florida. You can stay in a luxury villa in Cape Coral with stunning views over the water, a townhouse in Orlando, an apartment in Miami, just to name a few of your destinations and options available. We can help you find the perfect Florida vacation rental for you and your budget in seconds.
  • Are there unique natural phenomena in the Florida Keys, United States?

    Absolutely! The Florida Keys are known for their vibrant coral reefs, a unique ecosystem teeming with marine life. The area also experiences stunning sunsets, often cited as some of the best in the world. Birdwatching is excellent, with many species migrating through or residing in the Keys. The unique geography and climate also contribute to the diverse plant life found throughout the islands.
  • What are the most popular Airbnbs in Florida Keys?

  • Are there any unusual vacation rentals in Florida?

    Yes! Stay in a modern castle in Fort Lauderdale, a floating cottage in Sanford, a treehouse in the woods, or even a yurt with its own deck in Port St. Joe. You can find many quirky and unusual vacation rentals in Florida, and we can help you find the one you're looking for!
  • What essentials should you bring along for a trip to the Florida Keys, United States?

    Pack light clothing, swimwear, sunscreen (high SPF!), sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially if you plan on exploring the more natural areas. A reusable water bottle is crucial, as staying hydrated is important in the Florida Keys' climate. Consider bringing a waterproof bag for electronics and valuables if you plan on watersports.
  • What are the best vacation rentals with a pool in Florida Keys?

  • What are the top destinations in Florida?

    Top destinations in Florida include Sarasota, Orlando-Walt Disney World, St. Petersburg, FL, Key West, Naples, and Miami Beach.Florida's beaches are huge attractions, with the most popular being South Beach, Fort Lauderdale Beach, and Clearwater Beach. Of course, theme parks are a big draw for Florida, but you don't just have Walt Disney World, but also the Wizarding World of Harry Potter, Busch Gardens, and Universal Studios Florida. Art and culture lovers may want to visit the Salvador Dali Museum in St. Petersburg or the Hemingway House in Key West. Nature lovers will want to visit Dry Tortugas National Park or the Naples Botanical Garden.
  • What famous events or festivals are happening in the Florida Keys, United States?

    The Florida Keys host several events throughout the year. Key West's Fantasy Fest is a renowned costumed celebration in October. The annual Hemingway Days celebration in July honors the famous author's legacy. Numerous smaller festivals and events related to fishing, music, and art take place throughout the year in various Keys communities.
  • What are the best rentals for families and kids in Florida Keys?

  • What dishes should I try in Florida?

    Some typical Florida dishes to try are conch fritters, a type of sea snail that's fried in batter shrimp and grits, fried gator tail, Key lime pie, oysters, and ceviche. However, when in doubt, you can never go wrong with freshly caught fish.
  • Where can you find the best restaurants serving local dishes in the Florida Keys, United States, and what are the must-try specialties?

    The Florida Keys boast a diverse culinary scene. Key West has numerous excellent restaurants. Try the Blue Heaven for its casual atmosphere and Caribbean-inspired dishes. Latitudes, located at the Cheeca Lodge & Spa in Islamorada, offers stunning sunset views and fresh seafood. Many restaurants feature fresh, locally caught seafood, conch fritters, and Key lime pie—a must-try dessert.
  • What are the best rentals or Airbnbs with a jacuzzi in Florida Keys?

    The best vacation rentals or Airbnb with a jacuzzi in Florida Keys are Leaward Isle Island Retreat, Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality and Key West Villas.

  • What are some less-famous attractions in the Florida Keys, United States that are worth the visit?

    Beyond the well-known spots, consider exploring the smaller islands and quieter beaches. The National Key Deer Refuge provides a chance to see these endangered deer in their natural habitat. The History of Diving Museum in Islamorada offers a fascinating look at diving's past. Exploring the backcountry by kayak or paddleboard reveals hidden coves and mangroves, offering a different perspective of the Keys.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, United States?

    Visiting local markets, like the Key West Green Market, provides a chance to interact with locals and sample local produce. Attending community events and festivals offers insight into local traditions. Striking up conversations with bartenders and staff at smaller, locally-owned establishments can lead to interesting interactions and local insights. Consider taking a guided tour focused on the history and culture of the Keys.
  • What unique natural landscapes and terrain features can travelers explore in the Florida Keys, United States?

    The Florida Keys' unique landscape is defined by its low-lying islands, mangrove forests, and the only living coral reef in the continental US. Exploring the backcountry waterways by boat or kayak reveals hidden mangrove tunnels and diverse birdlife. The beaches vary from the white sands of Bahia Honda State Park to the more rugged shores of other islands. The diverse ecosystems offer a variety of landscapes to explore.
  • How many days are ideal for visiting the Florida Keys, United States, and what are some itinerary suggestions?

    Seven to ten days is ideal to explore the Keys thoroughly. A possible itinerary could involve three days in Key West, two in Islamorada, and two exploring the Upper Keys, including Marathon and Bahia Honda State Park. This allows for relaxation, exploration, and enjoying diverse activities. Adjust the itinerary based on your interests and preferred pace.

Nearby regions

Best Florida Keys vacation rentals with a balcony

149 M² House ∙ 3 Bedrooms ∙ 8 Guests - Florida Keys
9.6 30 reviews

149 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Marathon
This luxurious three-bedroom villa is located in the Indigo Reef Resort in Marathon, Florida Keys, approximately 145 kilometres south of Miami and 72 kilometres from Key West, offering easy access to the Gulf of Mexico and Atlantic Ocean via Vaca Cut.
The 148 square metre property boasts a private boat dock (up to 9.4 metres), a fully equipped kitchen, a swimming pool, fitness centre, and accommodates up to eight guests, with sunset views from its porch and upper balcony; resort amenities and fishing/diving opportunities are also available.
Casa Largo - Florida Keys
9.4 210 reviews

Casa Largo

house, Key Largo
This waterfront home is situated close to Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, both within a mile, and is within three miles of Jacob's Aquatic Center and Bluefin Rock Harbor Marina, making it an ideal location for exploring Key Largo's attractions. It has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom house offers 71 square metres of space and can accommodate up to eight guests. The property features a fully equipped kitchen, a swimming pool, a Jacuzzi, a terrace, a garden, a tennis court, and parking, providing ample opportunities for relaxation and entertainment.
Villa 5053 On Duck Key Boat Slip Available - Florida Keys
9.6 128 reviews

Villa 5053 On Duck Key Boat Slip Available

house, Duck Key
This waterfront holiday home is located in Duck Key, just 3.2 kilometres from Little Conch Key and Curry Hammock State Park, offering a peaceful setting close to nature. It has consistently received excellent ratings for location, cleanliness, and overall experience.
This two-bedroom property provides 84 square metres of space, comfortably accommodating up to six guests. The house is fully equipped with a kitchen, air conditioning, a terrace, a garden, and parking, as well as free Wi-Fi and beach towels, ensuring a relaxing and enjoyable stay.
Beachside Unit 34- Pool, Private Beach And Tiki's! - Florida Keys
9.7 118 reviews

Beachside Unit 34- Pool, Private Beach And Tiki's!

apartment, Key Colony Beach
This apartment is situated in Key Colony Beach, just a 10-minute walk from two beautiful beaches, Sunset Park Beach and Coco Plum Beach, offering easy access to the stunning waters of the Florida Keys. The property has received excellent ratings for location, cleanliness and user experience.
The apartment is a 43 square meter property with one bathroom, comfortably accommodating up to four guests. It offers a fully equipped kitchen, a private balcony, a swimming pool, a garden, and parking.

Best Florida Keys vacation rentals with parking

Coastal Comfort In Ocean Point Suites - Florida Keys
9.7 127 reviews

Coastal Comfort In Ocean Point Suites

apartment, Tavernier
This Tavernier apartment is situated just a short walk from the end of the pier, offering stunning views of the Atlantic Ocean and Florida Keys mangroves. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom apartment spans 91 square metres and can comfortably accommodate up to six guests. Amenities include a swimming pool, jacuzzi, tennis courts, a marina, a cafe, and a beach area, providing a range of activities and features for a relaxing getaway.
P34 - Beautiful 4 Bedroom 2 Bath, Single Family Ho - Florida Keys
9.6 42 reviews

P34 - Beautiful 4 Bedroom 2 Bath, Single Family Ho

apartment, Key Colony Beach
This waterfront property is situated in Key Colony Beach, just a short walk from Sunset Park Beach and Coco Plum Beach, offering easy access to the beautiful Florida Keys coastline. The property has received excellent reviews from previous guests, with high ratings for cleanliness, location, and overall experience.
The four-bedroom holiday home comfortably accommodates up to eight guests, providing ample space for families or groups of friends. Enjoy the private pool, outdoor barbecue area, and fully equipped kitchen, plus free Wi-Fi and a spacious patio for relaxing and soaking up the sunshine.
B Watervibe - Florida Keys
9.8 89 reviews

B Watervibe

barge, Marathon
This unique barge accommodation in the Florida Keys, near Marathon, offers a tranquil escape close to various fishing spots and kayaking opportunities.
The self-catering vessel sleeps two guests in one bedroom with one bathroom, boasting air conditioning, parking, and internet access, perfect for romantic getaways.
Kcb Tiki Hut Oasis: 37.5' Dock + Cabana Club! - Florida Keys
9.9 100 reviews

Kcb Tiki Hut Oasis: 37.5' Dock + Cabana Club!

apartment, Key Colony Beach
This canal-front apartment is located in Key Colony Beach, just 60 kilometres north of Key West, offering a tranquil escape with easy access to the island's attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a spacious two-bedroom, two-bathroom property with a floor area of 116 square metres, comfortably accommodating up to six guests. Enjoy a range of amenities including a private dock, a Tiki Hut with a barbecue, a fully equipped kitchen, a swimming pool, a garden, parking, and access to a private beach club with a bar, restaurant, and oceanfront pool.
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