Holiday Rentals in Florida Keys

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Florida Keys holiday rentals
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Best Holiday rentals and Airbnb offers in Florida Keys

Best family friendly Florida Keys holiday rentals

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

Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br - Florida Keys
9.4 130 reviews

Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br

apartment, Tavernier
This apartment in Tavernier is ideally located just a short walk from Baker's Cay Resort Beach and Harry Harris Park, with other attractions like Mariners Hospital and Florida Keys Dive Center within a 5km radius. The apartment enjoys excellent user, location, and cleanliness ratings, guaranteeing a comfortable and enjoyable stay.
The spacious apartment, measuring 78 square metres, comfortably accommodates up to 6 guests across two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a private pool and spa tub, a fully equipped kitchen, air conditioning, and a balcony perfect for relaxing and enjoying the Tavernier weather.
Tree Top Paradise - Florida Keys
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.
Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida. - Florida Keys
9.4 3 reviews

Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida.

apartment, Islamorada, Village of Islands
This one-bedroom apartment is located in Plantation Key Colony, a neighbourhood in Tavernier, just 160 kilometres from Miami International Airport and a short distance from the attractions of the Upper Keys. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has a modern and comfortable interior, ideal for families of up to four people. It offers a range of amenities including internet access, a kitchen with a fridge and microwave, air conditioning, a terrace or balcony, and a spa. Guests can enjoy a peaceful retreat while having easy access to a variety of activities such as fishing, diving, exploring museums, shopping, and beaches.
Key Largo Lake View Townhome - Florida Keys
9.0 31 reviews

Key Largo Lake View Townhome

apartment, Key Largo
This three-bedroom townhouse is located in the gated Kawama Yacht Club community in Key Largo, just off Mile Marker 100, within walking distance of restaurants and attractions like Dolphins Plus. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The accommodation offers a spacious layout with three bathrooms, comfortably accommodating up to eight guests. Amenities include a private marina with a boat ramp and trailer parking, two heated swimming pools, a saltwater lagoon, a sandy beach, a playground, outdoor BBQ areas, pickleball/tennis courts, and a fully equipped kitchen.

Best Florida Keys holiday rentals with a pool

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

Old Wooden Bridge Resort & Marina - Florida Keys
8.5 904 reviews

Old Wooden Bridge Resort & Marina

house, Big Pine Key
This property is located in Big Pine Key, just 25 miles from Florida Keys Aquarium Encounters and 15 miles from Seven Mile Bridge, offering a peaceful escape with easy access to local attractions. The house has received very good user ratings for its cleanliness and overall experience, and the location has been rated excellent.
The accommodation features a fully equipped kitchen, a private bathroom, and a terrace or balcony. Guests can enjoy the swimming pool, the garden, and the bar, as well as free Wi-Fi, parking, and a grill for outdoor cooking.
Cabins At Bonefish Bay - Florida Keys
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.
Ocean's Edge Vo Pad Boards, Kayak, Bikes-30 Min Kw - Florida Keys
9.9 88 reviews

Ocean's Edge Vo Pad Boards, Kayak, Bikes-30 Min Kw

apartment, Cudjoe Key
This oceanfront cottage on Cudjoe Key boasts direct Atlantic Ocean access and is approximately 48 kilometres from Duval Street in Key West.
Sleeping six, this recently renovated two-bedroom property offers a spacious open-plan layout, a private seawall with boat access, onsite water sports equipment (kayak, paddleboards, floats), and access to Venture Out Resort amenities including a swimming pool, hot tub, and tennis/pickleball courts.
Last Minute Aug'26 Deals! Oceanfrnt Lux 1350sf, Great Views &All Amenities Home! - Florida Keys
9.6 395 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.

Frequently asked questions about holiday rentals in Florida Keys

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

    The Florida Keys offer a plethora of iconic sights. Key West is a must, with its historic Duval Street, Ernest Hemingway Home and Museum, and the Southernmost Point Buoy. Further up the Keys, you'll find the Seven Mile Bridge, offering stunning views, and Bahia Honda State Park, known for its beautiful beaches and historic bridge. Don't miss exploring 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?

  • 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 Keys are renowned for their vibrant coral reefs, a unique ecosystem teeming with marine life. The area also experiences spectacular sunsets, often cited as some of the best in the world. Additionally, the unique geography of the islands creates microclimates and diverse habitats, supporting a wide variety of plant and animal life.
  • What are the most popular Airbnbs in Florida Keys?

    Among the Airbnbs in Florida Keys, Relaxed Boho Vibes & Views [ Ocean Pointe 2315], Waterfront Cabana 6 and Key Largo Villa - Kawama L1 - 3\/3 are the most popular ones.

  • 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 (essential!), sunglasses, a hat, and insect repellent. Comfortable walking shoes are a must, as is a reusable water bottle to stay hydrated in the warm climate. Consider bringing a waterproof bag for your phone and valuables if you plan on water activities.
  • What are the best holiday 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 well-known, ten-day Halloween celebration featuring elaborate costumes and parades. The annual Conch Republic Independence Celebration in Key West is another quirky and popular event.
  • 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?

    Key West has a fantastic culinary scene. Many restaurants offer fresh seafood, a staple of the Keys. Look for places serving Key lime pie (a must-try!), conch fritters, and stone crab claws (seasonal). Specific restaurant recommendations would depend on your exact location within the Keys and your preferences, but exploring local eateries will offer a great range of options.
  • What are the best rentals or Airbnbs with a jacuzzi in Florida Keys?

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

    Consider exploring the smaller, quieter islands like Marathon or Islamorada. These offer a more relaxed atmosphere and opportunities for kayaking, paddleboarding, and fishing. The History of Diving Museum in Islamorada is also a fascinating hidden gem.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, United States?

    Chatting with staff at local businesses, visiting smaller, family-run restaurants, and attending local events are great ways to interact with residents. Consider taking a guided tour focused on the history and culture of the Keys, which can offer insights from knowledgeable locals.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, United States?

    The Keys' unique landscape is defined by its shallow-water coral reefs, mangrove forests, and the string of low-lying islands themselves. Exploring these ecosystems through kayaking, snorkelling, or diving will reveal the beauty and fragility of this environment.
  • How many days are ideal for a visit to the Florida Keys, United States, and what are some itinerary suggestions?

    Seven to ten days allows for a good exploration of the Keys. A possible itinerary could involve spending a few days in Key West, exploring its attractions, then driving up the Overseas Highway, stopping at various state parks and smaller towns along the way. Another option is to focus on a specific area, like the Islamorada region, for a more relaxed pace.

Nearby regions

Best Florida Keys holiday rentals with a balcony

Oceanside Family Condo With Pool And Beach Access - Florida Keys
9.8 188 reviews

Oceanside Family Condo With Pool And Beach Access

apartment, Tavernier
This family-friendly apartment is located in Tavernier, a short 5 kilometre walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within a 5 kilometre radius. The accommodation has excellent user, location and cleanliness ratings.
The apartment has 2 bedrooms and 2 bathrooms spread over 84 square metres and can comfortably accommodate up to 4 guests. Amenities include a fully equipped kitchen, a washing machine, free Wi-Fi, a swimming pool, a jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.
Captain Pip's Marina & Hideaway - Florida Keys
8.7 2313 reviews

Captain Pip's Marina & Hideaway

resort, Marathon
Captain Pip's Marina & Hideaway is situated in Marathon, Florida, just 1.4 kilometres from the Seven Mile Bridge and 6.4 kilometres from Sombrero Beach. The resort enjoys a tranquil setting, perfect for a relaxing getaway. It has consistently received very good ratings for its cleanliness, location, and overall experience.
The resort offers a range of amenities and activities for guests to enjoy. The accommodation features a swimming pool, a terrace, a garden, a restaurant, and a bar, as well as a fitness centre. Guests can also rent boats, kayaks, and paddleboards, or take advantage of the on-site fishing, snorkelling, and parasailing opportunities.
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.
Paradise Awaits, Remodeled, Marina, Pickleball, Tennis, Pools, Salt Water Lagoon - Florida Keys
9.4 63 reviews

Paradise Awaits, Remodeled, Marina, Pickleball, Tennis, Pools, Salt Water Lagoon

apartment, Key Largo
This luxurious yacht is situated in a private community in Key Largo, just minutes from John Pennekamp Coral Reef State Park and a short drive from other attractions like Jimmy Johnson's Big Chill and Bluefin Rock Harbor Marina. The property has received excellent user ratings, highlighting its appeal and quality.
The yacht spans 86 square metres and can comfortably accommodate up to eight guests. It boasts a range of amenities, including a fully-equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, and parking, ensuring a comfortable and enjoyable stay.

Best Florida Keys holiday rentals with parking

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Florida Keys
8.6 59 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This charming cottage is situated in Summerland Key, just a short distance from Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to a variety of water activities. The cottage has received very good ratings from previous guests.
The property features two bedrooms and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests can enjoy the peaceful surroundings and take advantage of the cottage's proximity to restaurants, shops, and other amenities in the area.
Island Time | Ocean Pointe 1207 | Oceanfront 2br Condo In Key Largo - Florida Keys
9.0 102 reviews

Island Time | Ocean Pointe 1207 | Oceanfront 2br Condo In Key Largo

apartment, Tavernier
This two-bedroom apartment in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's laid-back charm. The apartment has received excellent user and location ratings and a very good cleanliness rating.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a washing machine, and a coffee/tea maker. Enjoy relaxing amenities like a TV, internet access, and a terrace/balcony, as well as the convenience of parking and an elevator.
Charming One Bedroom On The Edge Of The Everglades - Florida Keys
9.5 74 reviews

Charming One Bedroom On The Edge Of The Everglades

house, Country Walk
This secluded cottage in Country Walk, Florida, is situated on a 2-acre plot bordering the Everglades and is a 40km drive from Everglades National Park.
The single-storey property, sleeping up to four guests, features a well-equipped kitchen, air conditioning, private parking, and a gazebo overlooking the Everglades; enjoy access to a private organic garden and nearby nature trails.
Ocean/marina View - Pool - Free Kayaks Pickleball - Florida Keys
9.7 112 reviews

Ocean/marina View - Pool - Free Kayaks Pickleball

apartment, Key Largo
This yacht is located in the Kawama Yacht Club gated community at mile marker 100 in Key Largo, just a short distance from John Pennekamp Coral Reef State Park and Pilot House Marina. It has received excellent ratings for user experience, location, and cleanliness.
The yacht has two bedrooms and two bathrooms, spanning 121 square meters and comfortably accommodating up to six guests. You'll find a range of amenities including a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a terrace, a garden, and parking. Guests can also enjoy direct ocean views, access to a 3-acre saltwater lagoon, and the use of two kayaks for exploring the surrounding waters.
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