Holiday Rentals in Florida Keys

15393 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Florida Keys holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Tropical Getaway W/private Beach 1 Bd Condo - Florida Keys
8.0 12 reviews

Tropical Getaway W/private Beach 1 Bd Condo

apartment, Tavernier
This Tavernier condo, named 'Tropical Getaway w/Private Beach', offers private beach access and is a short walk (approximately 2.25 km) from Harry Harris Park Beach, conveniently located 4.8 km from Pigeon Key.
The 60 square metre apartment sleeps seven, boasting a fully equipped kitchen, private balcony with sea views, a swimming pool, jacuzzi, tennis court, and free Wi-Fi; nearby cycling opportunities further enhance the stay.
The Garden House Hot Tub Pool And Lush Garden Oasis - Florida Keys
9.5 141 reviews

The Garden House Hot Tub Pool And Lush Garden Oasis

house, Homestead
This Homestead property is located just 5.8 kilometres from the Fruit Spice Park and 6.6 kilometres from the Florida Keys Factory Shops, offering a peaceful retreat in a convenient location. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The four-bedroom house spans 214 square metres and comfortably accommodates up to 10 guests. This spacious home offers a private pool, a hot tub, a lush garden, a fully equipped kitchen, air conditioning, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
*New Modern* 3br/2ba Duplex/37' Dock/cabana/kayaks/bikes - Florida Keys
9.8 137 reviews

*New Modern* 3br/2ba Duplex/37' Dock/cabana/kayaks/bikes

apartment, Key Colony Beach
This apartment is located just a 2-minute walk from Sunset Park in Key Colony Beach, offering easy access to the Cabana Club and a canal leading to both the Ocean and the Gulf. It has consistently received excellent ratings for location, cleanliness, and user experience.
The 157 square metre apartment comfortably sleeps up to 8 guests in 3 bedrooms and 2 bathrooms. It features a spacious backyard with a multi-game table, bikes, kayaks, and a 6-burner grill, as well as a fully equipped kitchen, air conditioning, a swimming pool, and direct canal access with 11.4 metres of dockage.
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar - Florida Keys
9.0 78 reviews

Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar

apartment, Tavernier
This two-bedroom apartment is situated in Tavernier, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has received excellent ratings for location, cleanliness, and user experience.
The 77 square metre apartment can comfortably accommodate up to six guests and features a well-equipped kitchen, two bathrooms, and a private pool. Guests can enjoy a range of amenities including a washing machine, air conditioning, and a garden.

Best Florida Keys holiday rentals with a pool

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

Pines & Palms Resort - Florida Keys
9.2 2299 reviews

Pines & Palms Resort

resort, Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating.
The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
Drop Anchor Resort & Marina - Florida Keys
8.6 1689 reviews

Drop Anchor Resort & Marina

glamping, Islamorada, Village of Islands
This mobile home is located in Islamorada, just a short walk from Theater of the Sea and a short drive from Indian Key Historic Park, offering a convenient base for exploring the area. The mobile home has received very good ratings for cleanliness and user experience, and the location itself is rated excellent.
The mobile home features a kitchen with a fridge and microwave, air conditioning, and a terrace or balcony. Guests have access to a range of amenities, including a swimming pool, a bar, a tennis court, and a garden, as well as kayaks, paddleboards and Wi-Fi.
Isla Bella Beach Resort & Spa - Florida Keys
9.2 1376 reviews

Isla Bella Beach Resort & Spa

resort, Marathon
Isla Bella Beach Resort & Spa is located in Marathon, Florida, just 5 kilometres from Vaca Key and the Seven Mile Bridge. The resort has received excellent user ratings, with very good reviews for its location and cleanliness.
The resort offers a range of rooms and suites to suit different needs. Guests can enjoy a variety of amenities, including multiple swimming pools, a full-service spa, on-site dining, and water sports activities.
Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort - Florida Keys
9.8 63 reviews

Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort

house, Tavernier
The Dolphin houseboat is located in Tavernier, Florida Keys, on the Bayside at Mile Marker 91.7, offering a peaceful escape from the hustle and bustle of the Keys. It is situated in a protected cove of Community Harbor, between Key Largo and Islamorada, and has excellent user ratings.
The houseboat has two bedrooms and one bathroom, accommodating up to five guests in a comfortable 56 square metres of space. The houseboat has a well-equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and internet access, perfect for enjoying the beautiful surroundings and local attractions.

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

Keys Deal W/cafe & Pool Bar! Up To 20% Off Beachfront 1bd Sleeps 4. - Florida Keys
9.7 131 reviews

Keys Deal W/cafe & Pool Bar! Up To 20% Off Beachfront 1bd Sleeps 4.

apartment, Tavernier
This Tavernier apartment is located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, both offering a relaxed beach atmosphere, and is within 5 kilometres of Mariners Hospital and Florida Keys Dive Center. It has received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment spans 60 square metres and comfortably accommodates up to four guests. It offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
4 Bedroom/4 Bath: Coco Plum Home With Pool, Hot Tub + Dock. - Florida Keys
9.0 6 reviews

4 Bedroom/4 Bath: Coco Plum Home With Pool, Hot Tub + Dock.

apartment, Marathon
This luxurious waterfront property in Coco Plum, Marathon, Florida, enjoys direct beach access and is conveniently located near Captain Hooks Marina and Dive Centre and the Marathon Air Museum.
This four-bedroom, four-bathroom apartment boasts 250 square metres of living space, a private pool and hot tub, plus a full outdoor kitchen and kayak for guest use, comfortably accommodating up to ten guests.
Starfish Seas Ocean Pointe 1302 King/queen 2ba 2br - Florida Keys
9.8 30 reviews

Starfish Seas Ocean Pointe 1302 King/queen 2ba 2br

apartment, Tavernier
This two-bedroom apartment is situated in Tavernier, Florida, just halfway between Key Largo and Islamorada, offering easy access to the area's top attractions. The property has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The apartment comfortably sleeps four guests and boasts a modern design with updated kitchens and bathrooms. Guests have access to a range of amenities, including a swimming pool, hot tub, tennis courts, and a private sandy beach, providing ample opportunities for relaxation and recreation.
Ragged Edge Resort & Marina - Florida Keys
9.5 382 reviews

Ragged Edge Resort & Marina

resort, Islamorada, Village of Islands
Ragged Edge Resort & Marina is located in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty. The resort has consistently received excellent ratings for location, cleanliness, and overall experience.
The accommodation features a mix of rooms and suites, some with balconies offering sea views. Guests can enjoy amenities such as a swimming pool, terrace, free bikes, a communal grill, and free Wi-Fi.

Best Florida Keys holiday rentals with parking

King Suite | Heated Pool | Marathon Keys | Sleep 4 - Florida Keys
9.9 23 reviews

King Suite | Heated Pool | Marathon Keys | Sleep 4

apartment, Marathon
This ocean-view apartment is located in a gated fishing village on Marathon Key, Florida, approximately 105km from Key West International Airport (EYW).
The self-catering property boasts a king-size bed, queen-size sleeper sofa, two bathrooms, and a full kitchen with stainless steel appliances; guests can enjoy the heated pool, fish cleaning station, and proximity to the Atlantic Ocean waterfront with picnic area and kayak/canoe launch.
Key Largo Kawama Villa N2 - Florida Keys
9.4 135 reviews

Key Largo Kawama Villa N2

apartment, Key Largo
This three-bedroom, three-bathroom villa is located in the central Kawama district of Key Largo, offering direct access to a saltwater swimming lagoon and proximity to John Pennekamp Coral Reef State Park, Dagny Johnson Key Largo Hammock Botanical State Park, and MarineLab Undersea Laboratory.
This apartment provides accommodation for up to eight guests with resort-style amenities including multiple swimming pools, a fishing pier, marina, tennis courts, a fire pit, and bikes for exploring, making it an ideal base for diving, fishing, and boat tours.
Heated Pool In A Precious House Close To Zoo Parks And Arts - Florida Keys
9.8 294 reviews

Heated Pool In A Precious House Close To Zoo Parks And Arts

house, Cutler Bay
This Cutler Bay property is situated approximately 18 and 19 kilometres respectively from the University of Miami, offering convenient access to Zoo Miami and Fruit & Spice Park.
This five-bedroom, three-bathroom house boasts 232 square metres of floor space, including a private heated pool, free Wi-Fi, and parking, ideal for families or large groups seeking a comfortable stay near Cutler Bay's attractions.
Casa De Grouper With A Beautiful Canal View - Florida Keys
10 19 reviews

Casa De Grouper With A Beautiful Canal View

house, Marathon
This four-bedroom, three-bathroom apartment in Marathon, Florida Keys, is situated minutes from Sombrero Beach and local restaurants.
Offering stunning ocean views, a private dock, swimming pool, jacuzzi, parking and sleeping up to ten guests, this self-catering property provides easy access to various water activities.
©2026 cozycozy.com