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 11639 accommodations in Florida Keys, here are the 4 best family friendly rentals

The Perry Hotel & Marina Key West - Florida Keys
9.2 2522 reviews
Florida Keys
05/08 – 06/08
£1369/nightfor 1 night

The Perry Hotel & Marina Key West

6 13
resort , Stock Island
The Perry Hotel & Marina Key West is located on Stock Island, just 8km from Key West's Old Town and 5km from Key West International Airport. It has excellent user ratings, with particularly high marks for cleanliness and location.
The hotel has a waterfront setting with two pools and direct marina access. Guests can enjoy a range of amenities, including restaurants, a spa, a fitness centre, tennis courts, and complimentary shuttle service to Old Town.
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing - Florida Keys
10 11 reviews
Florida Keys
26/12 – 03/01
£1188/nighttotal: £9504 (8 )

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

4 10
apartment , Key Largo
This Key Largo townhouse, situated oceanside near Molasses Reef (beyond a 61-metre pier) and close to John Pennekamp Coral Reef State Park, offers direct access to a premier North American dive site.
The 206 square metre property boasts four bedrooms, three bathrooms, and resort-style amenities including two pools, a jacuzzi, tennis and pickleball courts, a fitness centre, and marina access for boats up to 18 metres.
Ocean Isles Yellowtail Row Vaca-25-84 - Florida Keys
10 1 review
Florida Keys
27/06 – 04/07
£145/nighttotal: £1015 (7 )

Ocean Isles Yellowtail Row Vaca-25-84

1 2
apartment , Marathon
This oceanfront Marathon condo, situated in a gated fishing village community, is approximately 16km from the Turtle Hospital, Dolphin Research Centre, and Sombrero Beach, and 40km from Bahia Honda State Park.
This one-bedroom, two-bathroom apartment sleeps four guests and boasts a kitchen with a fridge and microwave, air conditioning, free Wi-Fi, access to a heated pool, clubhouse, grills, and a fishing pier; enjoy nearby outdoor games such as cornhole, table tennis, and shuffleboard.
Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool - Florida Keys
9.8 98 reviews
Florida Keys
27/06 – 04/07
£332/nighttotal: £2324 (7 )

Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool

2 2
apartment , Islamorada, Village of Islands
This beachfront property is located in Islamorada, just under 5 kilometres from Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, and 3.5 kilometres from the History of Diving Museum. The home has received excellent ratings for location, cleanliness and user experience.
The house is spread over 149 square metres and can accommodate up to 6 guests. It features 2 bedrooms, 3 bathrooms, a fully equipped kitchen, a spacious balcony, a swimming pool, a jacuzzi, a garden, a spa and parking.

Best Florida Keys holiday rentals with a pool

Among the 11639 accommodations in Florida Keys, here are the 4 best rentals with a pool

Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo! - Florida Keys
9.6 90 reviews
Florida Keys
27/06 – 04/07
£250/nighttotal: £1750 (7 )

Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo!

2 2
apartment , Islamorada, Village of Islands
This Islamorada seaside apartment, near Old Road Gallery and Founders Park (within 3km), offers stunning ocean views and easy beach access.
The 79 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, free Wi-Fi, a pool, jacuzzi, and tennis court, plus barbecue facilities and limited housekeeping.
Ocean Front,  Marina, Pool/hot Tub, Private Beach, Bar/cafe - Florida Keys
9.2 154 reviews
Florida Keys
27/06 – 04/07
£151/nighttotal: £1057 (7 )

Ocean Front, Marina, Pool/hot Tub, Private Beach, Bar/cafe

1 2
apartment , Tavernier
This oceanfront apartment in Tavernier is a short distance from John Pennekamp Coral Reef State Park and Indian Key Historic State Park, offering easy access to the area's natural wonders. It has consistently received excellent user ratings, ensuring a comfortable and enjoyable stay.
The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, comfortably accommodating up to four guests. It boasts a range of amenities including a swimming pool, jacuzzi, spa, and private beach access, providing everything you need for a relaxing and enjoyable vacation.
Welcome To Paradise! - Florida Keys
9.6 86 reviews
Florida Keys
28/09 – 05/10
£164/nighttotal: £1148 (7 )

Welcome To Paradise!

1 2
apartment , Key Largo
This one-bedroom apartment is situated in the gated oceanfront community of Kawama Yacht Club in Key Largo, offering direct access to the ocean and a short walk to the beach. The apartment has received excellent user ratings, making it a popular choice for travellers.
The 84 square metre apartment can accommodate up to 4 guests and features a modern kitchen, a spacious living area with a convertible sofa bed and daybed, and a private balcony overlooking a nature preserve. Guests can enjoy a range of amenities, including three heated swimming pools, a saltwater lagoon with a sand beach, tennis and pickleball courts, a fishing jetty, and complimentary boat launch facilities.
Sombrero Beach House: 50' Dock, Pool, Bbq, Bicycles & More! - Florida Keys
9.4 53 reviews
Florida Keys
26/06 – 06/07
£420/nighttotal: £4200 (10 )

Sombrero Beach House: 50' Dock, Pool, Bbq, Bicycles & More!

3 6
apartment , Marathon
This Marathon waterfront property, a short distance from Sombrero Beach and easily accessible to the Seven Mile Bridge and Marathon Park, offers convenient access to local attractions.
This 135-square-metre (1453 sq ft) three-bedroom, two-bathroom house sleeps eight, boasting a private dock, above-ground pool, BBQ grill, and indoor games, plus free bicycle use for exploring the island.

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

P46 - Beautiful Updated Home On The Gulf Side With Pool And Dock! - Florida Keys
9.4 50 reviews
Florida Keys
28/09 – 05/10
£302/nighttotal: £2114 (7 )

P46 - Beautiful Updated Home On The Gulf Side With Pool And Dock!

2 2
apartment , Marathon
This waterfront property in Marathon is located just 5km from Crane Point Museum and Nature Center, Captain Hooks Marina and Dive Center, and Sunset Park Beach, making it a great base for exploring the area. The house has received excellent ratings for its cleanliness, location, and overall user experience.
The 2-bedroom house comfortably accommodates up to 6 guests. Enjoy modern amenities such as a private pool, a fully equipped kitchen, a spa tub, and a barbecue grill, all while taking in stunning views of the water.
Duck Key Getaway: Charming 3br Condo With Water Views, Steps From Angler & Ale, Near Marathon - Florida Keys
8.8 57 reviews
Florida Keys
26/12 – 03/01
£452/nighttotal: £3616 (8 )

Duck Key Getaway: Charming 3br Condo With Water Views, Steps From Angler & Ale, Near Marathon

3 10
apartment , Duck Key
This Duck Key holiday apartment is conveniently located near the Angler & Ale Restaurant and marina, a short drive from Marathon and an hour's drive from Key West.
This 121 square metre property boasts three bedrooms, two bathrooms, sleeps up to ten guests, features a fully equipped kitchen with a Keurig coffee maker, a screened porch with outdoor dining, covered parking for two cars, and is close to Coco Plum Beach (14km), Sombrero Beach (21km), and Bahia Honda State Park (51km).
Old Wooden Bridge Resort & Marina - Florida Keys
8.5 767 reviews
Florida Keys
27/06 – 04/07
£175/nighttotal: £1225 (7 )

Old Wooden Bridge Resort & Marina

1 2
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.
Islander Resort - Florida Keys
9.0 4007 reviews
Florida Keys
07/07 – 10/07
£215/nighttotal: £645 (3 )

Islander Resort

1 2
resort , Islamorada, Village of Islands
Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness.
The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.

Best Florida Keys holiday rentals with parking

Magic Ocean View. A Beautiful Place To Be Happy. - Florida Keys
9.8 8 reviews
Florida Keys
26/06 – 06/07
£245/nighttotal: £2450 (10 )

Magic Ocean View. A Beautiful Place To Be Happy.

1 6
apartment , Marathon
This three-bedroom, two-bathroom flat is located in Marathon, offering a peaceful retreat with convenient access to local attractions.
This apartment accommodates up to eight guests and features a kitchen, air conditioning, a Jacuzzi, and parking, providing a comfortable base for exploring the Florida Keys.
Beachside Unit 12 - Key Colony - Florida Keys
9.8 156 reviews
Florida Keys
01/09 – 04/09
£236/nighttotal: £708 (3 )

Beachside Unit 12 - Key Colony

1 2
apartment , Key Colony Beach
This apartment is situated in Key Colony Beach, just a short walk from Sunset Park Beach and Coco Plum Beach, and within 3km of Curry Hammock State Park and San Pablo Catholic Church. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The flat is 43 square metres and can accommodate up to four guests. You'll find a well-equipped kitchen, a balcony, and access to a swimming pool, barbecue grills, and a garden.
Licensed Mgr - 2/2 Villa - Oceanfront Beach Resort - Saltwater Lagoon & Marina! - Florida Keys
9.7 143 reviews
Florida Keys
04/08 – 07/08
£382/nighttotal: £1146 (3 )

Licensed Mgr - 2/2 Villa - Oceanfront Beach Resort - Saltwater Lagoon & Marina!

2 4
house , Key Largo
This charming two-bedroom house in Key Largo is just a short drive from John Pennekamp State Park and Pigeon Key, offering easy access to the area's natural beauty and attractions. The property boasts excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The 102 square metre house comfortably accommodates up to six guests and features a fully equipped kitchen, a private pool, a tennis court, and a spacious terrace with pool views. Guests can enjoy a range of activities on-site, including swimming, fishing, kayaking, and relaxing in the garden.
M18 - Spacious 3 Bedroom, 2 Bath Gulf Side Condo! - Florida Keys
9.5 14 reviews
Florida Keys
27/06 – 04/07
£277/nighttotal: £1939 (7 )

M18 - Spacious 3 Bedroom, 2 Bath Gulf Side Condo!

3 2
apartment , Marathon
This three-bedroom apartment is situated near Fishermen's Community Hospital in Marathon, within easy reach of Vaca Key and Pigeon Key Foundation. The property has received excellent ratings for location, cleanliness, and user experience.
The apartment is ideal for families or groups of up to six guests. Amenities include a private pool, barbecue grills, parking, a fully equipped kitchen, a balcony, and a garden, perfect for enjoying the Florida Keys lifestyle.
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