Holiday Rentals in Florida Keys, FL

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Florida Keys, FL holiday rentals
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11639 Holiday Rentals and Airbnb in Florida Keys, FL

Best family friendly Florida Keys, FL holiday rentals

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

🌴Ms. Marriott’s 12+beds Luxury Stay. - Florida Keys, FL
10 2 reviews
Florida Keys, FL
24/07 – 27/07
NZ$1530/nighttotal: NZ$4590 (3 )

🌴Ms. Marriott’s 12+beds Luxury Stay.

1 14
house , Kendall
This multi-family residence in Kendall offers a strategic base for exploring South Florida, situated conveniently near Zoo Miami and major expressways for easy access to Miami Beaches, the Everglades, and the Florida Keys.
This property can accommodate up to 19 guests across three independent units or the entire building, featuring multiple full kitchens, a SwimSpa, a large courtyard, and is well-equipped for events such as weddings and family reunions.
Save Big $$$ June!!  Waterfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds - Florida Keys, FL
9.5 438 reviews
Florida Keys, FL
09/07 – 13/07
NZ$640/nighttotal: NZ$2560 (4 )

Save Big $$$ June!! Waterfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds

2 4
apartment , Cudjoe Key
This holiday home is located in Summerland Key, just a short walk from Venture Key and Venture Out Keys, and less than 800 metres from Out Key. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property offers 80 square metres of living space, comfortably accommodating up to six guests in two bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
Knowles House/free Onsite Parking/close To Duval - Florida Keys, FL
10 32 reviews
Florida Keys, FL
05/08 – 06/08
NZ$3612/nightfor 1 night

Knowles House/free Onsite Parking/close To Duval

7 13
apartment , Key West
This seven-bedroom, eight-bathroom Key West house is situated in Old Town, less than 0.8km from Duval Street, offering easy access to Eaton Street's restaurants and the free Duval Loop shuttle.
Sleeping fourteen guests, this property boasts a swimming pool, garden, parking for two cars, and multiple relaxation areas including a poolside workspace, plus self check-in and nearby bike rentals at Eaton Bikes.
Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures - Florida Keys, FL
9.8 483 reviews
Florida Keys, FL
09/07 – 13/07
NZ$871/nighttotal: NZ$3484 (4 )

Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures

2 4
houseboat , Islamorada, Village of Islands
This houseboat is located at Mile Marker 90, just south of Key Largo, offering easy access to the ocean and the bay via Tavernier Creek. The property has received excellent ratings from previous guests for its location, cleanliness and overall experience.
The houseboat spans 111 square metres and can accommodate up to four guests. It boasts a fully equipped kitchen, a terrace, a garden, a spa, a fitness centre, and parking, as well as access to a range of activities and services at the marina.

Best Florida Keys, FL holiday rentals with a pool

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

Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar - Florida Keys, FL
9.7 127 reviews
Florida Keys, FL
01/09 – 04/09
NZ$518/nighttotal: NZ$1554 (3 )

Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar

2 2
apartment , Tavernier
This waterfront apartment is situated in Tavernier, just a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and scenic location close to the area's attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment spans 87 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. It features a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Cottage With Swimming Pool And Dockage, Just Minutes To Key West! - Florida Keys, FL
9.0 314 reviews
Florida Keys, FL
27/06 – 04/07
NZ$326/nighttotal: NZ$2282 (7 )

Cottage With Swimming Pool And Dockage, Just Minutes To Key West!

1 2
cottage , Cudjoe Key
This Cudjoe Key oceanfront cottage offers stunning views and direct beach access, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 36-square-metre self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, private terrace, swimming pool, and free Wi-Fi.
Best Catch On Grouper Ln At Ocean Isles - Florida Keys, FL
10 3 reviews
Florida Keys, FL
27/06 – 04/07
NZ$403/nighttotal: NZ$2821 (7 )

Best Catch On Grouper Ln At Ocean Isles

1 2
apartment , Marathon
This Marathon Shores beachfront condo offers direct ocean access and is a short drive from Sombrero Beach and Curry Hammock State Park.
The 850-square-metre (9150 sq ft) apartment features one bedroom, two bathrooms, sleeps four, and includes a fully equipped kitchen, private balcony, and access to an Olympic-size swimming pool, tiki huts, and a fishing pier.
Florida Keys Resort-style Home W/ Pool & Dock 5/3 - Florida Keys, FL
9.9 172 reviews
Florida Keys, FL
26/12 – 03/01
NZ$3389/nighttotal: NZ$27112 (8 )

Florida Keys Resort-style Home W/ Pool & Dock 5/3

5 10
apartment , Marathon
This five-bedroom apartment is situated in Marathon, Florida, just a short distance from the Atlantic Ocean and a two-minute boat ride to open water, offering a peaceful escape from the hustle and bustle. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment spans 163 square meters and comfortably accommodates up to 12 guests. Amenities include a private dock, a swimming pool, a hot tub, a garden, and a terrace, along with modern conveniences such as a fully equipped kitchen, air conditioning, and parking.

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 beautiful Mallory Square sunset celebration. Further up the Keys, you'll find the John Pennekamp Coral Reef State Park, perfect for snorkelling and diving, and the Seven Mile Bridge, an engineering marvel offering stunning views. Don't miss the historic lighthouse at Key West and the charming shops and restaurants throughout the islands.
  • What are the best Airbnb and holiday rentals in Florida Keys, FL?

    Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality, Leaward Isle Island Retreat 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 Florida Keys are known for their vibrant coral reefs, a unique ecosystem teeming with marine life. The annual migration of birds through the Keys is another spectacular natural event. You can also witness stunning sunsets, particularly from Mallory Square in Key West.
  • What are the most popular Airbnbs in Florida Keys, FL?

    Among the Airbnbs in Florida Keys, FL, 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, FL, 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 Florida heat. Don't forget your camera to capture the stunning scenery!
  • 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 popular Halloween celebration known for its vibrant costumes and parades. The Conch Republic Independence Celebration in Key West is another quirky and fun 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 boast a diverse culinary scene. For fresh seafood, try the Blue Heaven in Key West, known for its laid-back atmosphere and delicious Key lime pie. Another popular choice is Louie's Backyard, also in Key West, offering stunning waterfront views. Key lime pie, conch fritters, and stone crab claws are local must-try dishes.
  • 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, a historic boat featured in a Humphrey Bogart film, in Key Largo. The History of Diving Museum in Islamorada is another hidden gem. Explore the various smaller, quieter beaches along the Overseas Highway for a more secluded experience.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?

    Chatting with locals at smaller, family-run restaurants and bars is a great way to learn about the Keys' culture. Attend local events and festivals to experience the community spirit. Visiting local markets and interacting with artisans can also provide insights into the local way of life.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, FL, United States?

    The Florida Keys' unique landscape is defined by its coral reefs, mangrove forests, and the Overseas Highway, a scenic road spanning the islands. Explore the various beaches, each with its own character, and take a boat trip to see the diverse marine life.
  • 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 in Key Largo, allowing time for relaxation and activities. Adjust based on your interests and preferred pace.

Nearby regions

Best Florida Keys, FL holiday rentals with a balcony

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball - Florida Keys, FL
10 44 reviews
Florida Keys, FL
26/12 – 03/01
NZ$3742/nighttotal: NZ$29936 (8 )

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball

4 10
apartment , Key Largo
This five-bedroom, three-bathroom Key Largo oceanfront condo, situated within the Mariner's Club, offers unparalleled access to Molasses Reef and is adjacent to the community marina and pool.
The 10-guest property boasts a terrace, garden, swimming pool, spa, tennis court, and full kitchen, plus proximity to John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Hyatt Centric Key West Resort & Spa - Florida Keys, FL
8.8 2731 reviews
Florida Keys, FL
05/08 – 06/08
NZ$3384/nightfor 1 night

Hyatt Centric Key West Resort & Spa

6 13
resort , Key West
The Hyatt Centric Key West Resort & Spa is situated on Key West Island, just a short walk from the lively Duval Street, known for its nightlife and restaurants. The resort has received very good user ratings, with excellent marks for location and very good ratings for cleanliness.
The hotel has a waterfront location with a swimming pool, a jacuzzi and a spa. Guests can enjoy a range of activities, including relaxing by the pool, exploring the surrounding area via jet ski, scuba diving, snorkelling, and island tours, as well as dining at two on-site restaurants.
Santa Maria Suites Resort - Florida Keys, FL
9.4 2561 reviews
Florida Keys, FL
24/07 – 27/07
NZ$4386/nighttotal: NZ$13158 (3 )

Santa Maria Suites Resort

6 14
resort , Key West
The Santa Maria Suites Resort is located just one block from the Atlantic Ocean and Duval Street, placing you right in the heart of Key West's lively atmosphere. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and 48-inch flat-screen TVs, ideal for a comfortable stay. Guests can enjoy a range of amenities including two outdoor heated pools, a spa, a fitness centre, and a restaurant serving Japanese cuisine.
Manatee Bay: Escape To This 2br Duck Key Villa, Private Patio, Dip Pool & Easy Access To Marathon - Florida Keys, FL
9.4 81 reviews
Florida Keys, FL
04/08 – 07/08
NZ$640/nighttotal: NZ$1920 (3 )

Manatee Bay: Escape To This 2br Duck Key Villa, Private Patio, Dip Pool & Easy Access To Marathon

2 4
apartment , Duck Key
This charming house is situated in Marathon, Florida, just 5 kilometers from Little Conch Key, Curry Hammock State Park, and Walkers Island, offering a peaceful retreat close to popular attractions. It has received excellent ratings for location, cleanliness, and user experience.
The property spans 84 square meters and comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. The house features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking, as well as internet access, making it ideal for a relaxing and enjoyable stay.

Best Florida Keys, FL holiday rentals with parking

Mia Mansion W/ Pool / Bbq /Cabanna / Outdoor Bar - Florida Keys, FL
8.7 3 reviews
Florida Keys, FL
05/08 – 06/08
NZ$1657/nightfor 1 night

Mia Mansion W/ Pool / Bbq /Cabanna / Outdoor Bar

5 13
house , Sunset
This Tamiami villa, situated 8.8km from the University of Miami and close to Miami International Mall, Dolphin Mall, and CocoWalk Shopping Centre, offers convenient access to major attractions.
This five-bedroom property boasts 325 square metres of floor space, accommodating up to 31 guests, and includes a private pool with a pool bar and hot tub, plus a fully equipped kitchen, free Wi-Fi, and ample private parking.
Sunrise Breeze On The Marina [Ocean Pointe 5302] - Florida Keys, FL
9.8 173 reviews
Florida Keys, FL
01/09 – 04/09
NZ$518/nighttotal: NZ$1554 (3 )

Sunrise Breeze On The Marina [Ocean Pointe 5302]

2 2
apartment , Tavernier
This Tavernier beach apartment is conveniently located within a 10-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 85 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. This family-friendly apartment includes a range of amenities such as a swimming pool, Jacuzzi, tennis court, and a garden, ensuring a comfortable and enjoyable stay.
Isla Bella Beach Resort & Spa - Florida Keys - Florida Keys, FL
8.8 587 reviews
Florida Keys, FL
24/07 – 27/07
NZ$3509/nighttotal: NZ$10527 (3 )

Isla Bella Beach Resort & Spa - Florida Keys

5 14
resort , Marathon
Isla Bella Beach Resort & Spa - Florida Keys is located in Marathon, Florida, just a short drive from the Seven Mile Bridge and other popular attractions. The resort has received excellent ratings for its location, cleanliness, and overall experience.
The hotel features a private beach, a spa, and a fitness centre. Guests can enjoy a variety of activities such as cycling, fishing, and exploring the surrounding Keys.
Toes In The Sand - 2 Bedroom Condo Sleeps 4 - Florida Keys, FL
9.6 653 reviews
Florida Keys, FL
01/09 – 04/09
NZ$362/nighttotal: NZ$1086 (3 )

Toes In The Sand - 2 Bedroom Condo Sleeps 4

1 2
apartment , Tavernier
This apartment is situated in Ocean Pointe Suites, located between Key Largo and Islamorada, just a short distance from Tavernier's main attractions. The property has received excellent ratings for its location, cleanliness and overall experience.
The apartment is perfect for families, with a pull-out sofa bed and convertible chair for comfortable sleeping arrangements. Guests can enjoy a range of amenities, including a heated pool, hot tub, tennis courts, pickleball courts, a playground, BBQ areas, a marina with boat slip rentals, a full kitchen, laundry facilities, free high-speed WiFi and a cooler.
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