Vacation Rentals in Florida Keys, FL

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Florida Keys, FL holiday rentals
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15393 Holiday rentals and Airbnb in Florida Keys, FL

Best family friendly Florida Keys, FL holiday rentals

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

Full Time Lic Mgr - Modern 3 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy! - Florida Keys, FL
9.7 514 reviews

Full Time Lic Mgr - Modern 3 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy!

house, Key Largo
This luxurious penthouse suite in Key Largo is located just a short drive from popular attractions like Pigeon Key and John Pennekamp State Park, offering easy access to the best of what the area has to offer. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The suite features three bedrooms and three bathrooms, providing ample space for families or groups of friends. Guests can enjoy a range of amenities, including a private pool with stunning ocean views, a fully equipped kitchen, a fitness centre, a tennis court, and a spa.
Last Minute Aug'26 Deals! Oceanfrnt Lux 1350sf, Great Views &All Amenities Home! - Florida Keys, FL
9.6 396 reviews

Last Minute Aug'26 Deals! Oceanfrnt Lux 1350sf, Great Views &All Amenities Home!

apartment, Key Largo
This beachfront apartment is located in the heart of Key Largo, within a mile of Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, making it perfect for exploring the area's attractions. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment spans 125 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. It offers a range of amenities for a relaxing and enjoyable stay, including a private pool, a fully equipped kitchen, free Wi-Fi, and a DVD player, as well as a terrace, garden, and access to a spa, tennis court, and parking.
Tree Top Paradise - Florida Keys, FL
8.8 53 reviews

Tree Top Paradise

house, Cudjoe Key
Tree Top Paradise, a holiday home in Cudjoe Key, Florida, is situated approximately 37 kilometres from the Ernest Hemingway Home and Museum and Duval Street, and 39 kilometres from the Southernmost Point.
This 78-square-metre property boasts two bedrooms, two bathrooms, sleeps up to 11 guests, and includes a private pool, Jacuzzi, tennis court, and free Wi-Fi; nearby activities include snorkelling, cycling, and fishing.
Chesapeake Beach Resort - Florida Keys, FL
9.0 2595 reviews

Chesapeake Beach Resort

resort, Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park and directly on the oceanfront, offering stunning ocean views and easy access to the beach. The resort has received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of rooms and suites, all featuring a 37-inch flat-screen cable TV and a small refrigerator. Guests can enjoy an outdoor pool with ocean views, a Jacuzzi, a terrace or balcony, a garden, and a restaurant and bar on-site.

Best Florida Keys, FL holiday rentals with a pool

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

Cabins At Bonefish Bay - Florida Keys, FL
9.3 474 reviews

Cabins At Bonefish Bay

resort, Marathon
Cabins At Coconut Cay RV and Marina is located in Marathon, Florida, just 2.3 kilometres from Florida Keys Aquarium Encounters and 2.4 kilometres from Captain Hook's Marina Dive Center. The resort has received excellent ratings for its location, cleanliness, and overall user experience.
The cabins offer 399 square metres of space and can accommodate up to six guests. Amenities include a swimming pool, free Wi-Fi, parking, and air conditioning, along with a peaceful garden setting and comfortable rooms with flat-screen TVs and private bathrooms.
New Waterview 2/1 Cabins W Boat Ramp (No Loft) - Florida Keys, FL
9.5 144 reviews

New Waterview 2/1 Cabins W Boat Ramp (No Loft)

cabin, Marathon
This family-friendly holiday home in Marathon, Florida offers easy access to local beaches and attractions.
The two-bedroom, one-bathroom lodge sleeps six, boasting a fully equipped kitchen, air conditioning, a private swimming pool, and complimentary use of kayaks, paddle boards and bikes, plus a private pickleball court and on-site boat launch.
Miami Relax Oasis  Firepit, Mini Golf | Pool_bbq - Florida Keys, FL
9.6 141 reviews

Miami Relax Oasis Firepit, Mini Golf | Pool_bbq

apartment, Country Walk
This five-bedroom apartment is located in Country Walk, just a short distance from the lively South Beach area of Miami. It has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment features a spacious layout, comfortably accommodating up to 14 guests. Amenities include a private heated pool, a mini beach area, a fully equipped kitchen, a pool table, a BBQ, and 24/7 services.
Beautiful Condo With A Balcony - Florida Keys, FL
9.8 59 reviews

Beautiful Condo With A Balcony

apartment, Tavernier
This Tavernier apartment, boasting stunning mangrove views, is situated near Harry Harris Park, a short drive from the ocean and offering easy access to the Tavernier marina.
The one-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen, air conditioning, a private swimming pool and jacuzzi, plus smart lock security and access to resort-style amenities.

Frequently asked questions about holiday rentals in Florida Keys, FL

  • What are the must-see sights in the Florida Keys, FL, 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 vibrant Duval Street. Further up the Keys, you'll find the stunning Seven Mile Bridge, offering breathtaking views, and Bahia Honda State Park, known for its beautiful beaches and historic bridge. Don't miss the John Pennekamp Coral Reef State Park, a great place for snorkelling or diving.
  • What are the best Airbnb and holiday rentals in Florida Keys, FL?

    Leaward Isle Island Retreat, Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality and Relaxed Boho Vibes & Views [ Ocean Pointe 2315] are the most popular Airbnb and holiday rentals in Florida Keys, FL among travellers.

  • 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, FL, United States?

    Absolutely! The Keys are known for their vibrant coral reefs, a unique ecosystem teeming with marine life. Witnessing the sunset from Mallory Square in Key West is another unforgettable experience. The unique geography of the islands, formed by coral reefs, also creates stunning natural landscapes.
  • What are the most popular Airbnbs in Florida Keys, FL?

  • 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, FL, United States?

    Pack light clothing, swimwear, sunscreen (essential!), sunglasses, a hat, and insect repellent. Comfortable walking shoes are a must, especially if you plan on exploring the many parks and trails. Don't forget your camera to capture the stunning scenery, and a reusable water bottle to stay hydrated in the warm climate.
  • What are the best holiday rentals with a pool in Florida Keys, FL?

  • 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, FL, United States?

    The Florida Keys host several events throughout the year. Key West's Fantasy Fest is a well-known, ten-day costuming and masking event held in October. The Key West Conch Republic Independence Celebration in April is another popular event.
  • What are the best rentals for families and kids in Florida Keys, FL?

  • 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, FL, United States, and what are the must-try specialties?

    The Keys have a vibrant culinary scene. Try a restaurant in Key West like Blue Heaven for its famous Key Lime Pie and Caribbean-inspired dishes. In Islamorada, Morada Bay Beach Cafe offers fresh seafood with waterfront views. Key lime pie and fresh seafood are must-try local specialties.
  • What are the best rentals or Airbnbs with a jacuzzi in Florida Keys, FL?

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

    Consider visiting the African Queen, the boat used in the film of the same name, moored in Key Largo. The History of Diving Museum in Islamorada is also a fascinating place to explore, showcasing the evolution of diving equipment. Exploring the backcountry by kayak or boat can reveal hidden coves and mangroves.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?

    Visiting local markets, like the Key West Green Market, offers a chance to interact with locals and experience the local produce. Chatting with staff at smaller, family-run businesses provides insights into the Keys' culture. Participating in local events and festivals also offers opportunities for cultural immersion.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, FL, United States?

    The Keys' unique landscape is defined by its low-lying islands, mangrove forests, and of course, the coral reefs. Exploring the Everglades National Park (partially in the Keys) reveals diverse ecosystems including sawgrass prairies and cypress swamps. The diverse marine life is another key feature of the natural landscape.
  • How many days are ideal for a trip to the Florida Keys, FL, United States, and what are some itinerary suggestions?

    Seven to ten days allows for a good exploration of the Keys. A possible itinerary could include three days in Key West, two in Islamorada, and two exploring the Upper Keys, including Key Largo and Marathon. This allows for relaxation and exploration of different areas.

Nearby regions

Best Florida Keys, FL holiday rentals with a balcony

Tropical Escape | Sea Gulls 407 ~ Weekly Rental - Florida Keys, FL
9.6 53 reviews

Tropical Escape | Sea Gulls 407 ~ Weekly Rental

apartment, Islamorada, Village of Islands
This two-bedroom apartment is situated on Plantation Key, just a short distance from the heart of Islamorada, the sport fishing and diving capital of the Florida Keys. The apartment has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment offers a spacious and open layout, comfortably accommodating up to four guests. It boasts a range of modern amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a fitness centre, and covered parking. Guests can also enjoy kayaking, taking advantage of the apartment's convenient location and the beautiful waters of the Florida Keys.
Garden Cottage Near Miami, Everglades & Florida Keys - Florida Keys, FL
9.5 127 reviews

Garden Cottage Near Miami, Everglades & Florida Keys

apartment, Princeton
This one-bedroom apartment is located in Homestead, Florida, approximately 5.5 kilometres from Fruit Spice Park and 10.8 kilometres from the Florida Keys Factory Shops.
The 46 square metre apartment features a private garden, a fully equipped kitchen with a dishwasher, air conditioning, free private parking, and free Wi-Fi.
Coastal Charm: 2br Condo, Patio, Pool Views, Beach - Florida Keys, FL
9.3 80 reviews

Coastal Charm: 2br Condo, Patio, Pool Views, Beach

apartment, Marathon
This beachfront apartment is situated in Marathon, just a 1.6km walk from Curry Hammock State Park and Coco Plum Beach, offering easy access to the beautiful natural surroundings. The apartment has consistently received excellent user and location ratings, alongside a very good cleanliness rating.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It comes equipped with a fully fitted kitchen, a private terrace, access to a swimming pool, a gym, tennis courts, and a spa, ensuring a relaxing and enjoyable stay.
Welcome To The Pelican Lodge ! - Florida Keys, FL
8.9 58 reviews

Welcome To The Pelican Lodge !

apartment, Tavernier
This beachfront Tavernier apartment offers direct private beach access, a 2.6km walk from Harry Harris Park Beach and a 4.8km drive from Pigeon Key.
The two-bedroom, two-bathroom flat sleeps eleven guests and boasts a fully equipped kitchen, swimming pool, jacuzzi, tennis court, bar, free Wi-Fi, and sea views from its terrace.

Best Florida Keys, FL holiday rentals with parking

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis - Florida Keys, FL
10 90 reviews

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

apartment, Tavernier
This Ocean Pointe condo in Tavernier is a short walk (less than 1 km) from the beach, 5 minutes (approx. 5 km) from Tavernier's town centre, and 15 minutes (approx. 15 km) from John Pennekamp Coral Reef State Park.
The fully remodelled two-bedroom, two-bathroom apartment sleeps six, boasts a fully equipped kitchen, resort access with a swimming pool, jacuzzi, and tennis/pickleball courts, plus high-speed Wi-Fi and private beach access.
Sugarloaf Key Rv Resort & Cottages - Florida Keys, FL
9.1 640 reviews

Sugarloaf Key Rv Resort & Cottages

house, Cudjoe Key
This one-bedroom house, part of the Sun Outdoors Sugarloaf Key resort in Summerland Key, is situated approximately 27 kilometres from Key West International Airport and 32 kilometres from the Ernest Hemingway Home and Museum and Duval Street.
The 37-square-metre property sleeps six guests and boasts a private patio, swimming pool, bar, free Wi-Fi, and on-site parking, alongside a fully equipped kitchen, bathroom and air conditioning.
Flakey's - Florida Keys, FL
9.9 219 reviews

Flakey's

apartment, Islamorada, Village of Islands
This apartment is located on Morada Way in Islamorada's Art and Culture district, just across the street from Morada Bay and a short walk to World Wide Sportsman Marina, making it ideal for exploring the area. The property has excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to six guests. It comes equipped with a kitchen, air conditioning, parking, and internet access, as well as a spacious backyard garden perfect for enjoying the Florida sunshine.
Valhalla Beach House - Florida Keys, FL
9.9 100 reviews

Valhalla Beach House

apartment, Marathon
This two-bedroom, two-bathroom Florida Keys house in Marathon offers a central location, providing easy access to local attractions.
The property boasts a resort-style tropical backyard with a private pool, a game room with a pool table and ping-pong, and sleeps up to six guests, complete with a fully equipped kitchen and covered patio furniture; an optional pool heater is available for an additional fee.
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