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

94 M² House ∙ 2 Bedrooms ∙ 6 Guests - Florida Keys, FL
10 2 reviews

94 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Marathon
This canal-front property in Marathon, Florida, offers direct access to the Atlantic Ocean via Vaca Cut, providing excellent fishing and boating opportunities.
The 93 square metre (1000 square foot) house features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, spa, fitness centre, and a private dock with a fish cleaning station; perfect for families or groups exploring the Florida Keys.
Updated Key Largo Townhome  Pool  Saltwater Lagoon  Beach  Oceanfront Access - Florida Keys, FL
10 85 reviews

Updated Key Largo Townhome Pool Saltwater Lagoon Beach Oceanfront Access

apartment, Key Largo
This three-bedroom townhouse is located in the gated community of Kawama Yacht Club in Key Largo, Florida, directly on the Atlantic Ocean and within walking distance of a swimming pool, playground, saltwater lagoon, and oceanside beach. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
The 84 square metre townhouse can comfortably accommodate up to six guests and features a fully equipped kitchen, three bathrooms, air conditioning, a terrace, a spa, and parking. Guests can enjoy a range of on-site amenities, including a swimming pool, playground, saltwater lagoon, and fishing jetty, as well as easy access to local attractions such as Jimmy Johnson's Big Chill, Bluefin Rock Harbor Marina, and John Pennekamp Coral Reef State Park.
Chesapeake Beach Resort - Florida Keys, FL
9.0 2576 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.
Sea Mist - Oceanfront-lake-kayak-paddleboard-bike - Florida Keys, FL
9.7 310 reviews

Sea Mist - Oceanfront-lake-kayak-paddleboard-bike

apartment, Key Largo
This beachfront apartment in Key Largo is ideally situated just 4.6 miles from John Pennekamp State Park and 5.6 miles from Pigeon Key, offering easy access to the area's natural wonders. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious, covering 125 square metres and comfortably accommodating up to six guests. It boasts a fully equipped kitchen, a private pool, a terrace, a garden, and a range of amenities, including a spa, a bar, and a tennis court. Guests can also enjoy complimentary kayaks, paddleboards, and bikes, as well as access to nearby water sports activities.

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

Anglers Paradise ~ Waterfront Condo With Boat Slip - Florida Keys, FL
9.9 15 reviews

Anglers Paradise ~ Waterfront Condo With Boat Slip

apartment, Marathon
This Marathon, Florida waterfront condo boasts direct ocean access with a private 30-foot boat slip and ramp, conveniently located near local restaurants and beaches.
The two-bedroom, one-bathroom apartment sleeps four, featuring a fully equipped kitchen, east-facing balcony with sunrise views, a shared swimming pool, two parking spaces, and on-site fish cleaning facilities.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Florida Keys, FL
8.0 1 review

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Islamorada, Village of Islands
This oceanfront holiday home in Islamorada, Village of Islands, is located at Mile Marker 83 and offers direct access to the Atlantic Ocean and a private sandy beach, with a skiff dock suitable for shallow draft boats.
This spacious 4-bedroom, 3-bathroom villa accommodates up to 8 guests and features a heated beachside swimming pool, a separate spa, a garden cottage, and is a noted destination for weddings, providing excellent amenities and activities for families and pets.
Isle Be Back To The Sunny Keys - Florida Keys, FL
9.6 35 reviews

Isle Be Back To The Sunny Keys

cottage, Cudjoe Key
This charming cottage is located on Summerland Key, just a short drive from Cudjoe Key, and is close to both the Coupon Bight Aquatic Preserve and Bahia Honda State Park, offering easy access to beautiful natural surroundings. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The cottage spans 74 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. It features a well-equipped kitchen, a large patio with outdoor seating, a swimming pool, a jacuzzi, a garden, and free Wi-Fi, providing everything you need for a relaxing and enjoyable holiday.
Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada - Florida Keys, FL
9.6 85 reviews

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada

apartment, Islamorada, Village of Islands
This charming cottage is situated in Islamorada, just a short distance from the Village of Islands' centre, offering easy access to fishing piers and the lively downtown area. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for a relaxing getaway.
The cottage comfortably sleeps four guests in two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private backyard, a community pool, a fully equipped kitchen, a washer and dryer, a private porch, and bikes for exploring the area.

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

Dolphin Cove- Pet Friendly Waterfront Townhome W Pool - Florida Keys, FL
No reviews

Dolphin Cove- Pet Friendly Waterfront Townhome W Pool

house, Marathon
Dolphin Cove, a waterfront townhouse in Marathon, Florida, offers stunning sea views and is a short walk (less than 1 km) from Coco Plum Beach and 3.4 km from the Florida Keys Aquarium Encounters.
This 136 square metre, two-bedroom, two-bathroom property sleeps up to 11 guests and boasts a private swimming pool, spa, fitness centre, and free Wi-Fi; nearby attractions include A Deep Blue Dive Center (2.4 km) and Upper Matecumbe Key (47 km).
Family Favorite- Heated Pool, 2 Kings, Everglades - Florida Keys, FL
9.4 25 reviews

Family Favorite- Heated Pool, 2 Kings, Everglades

house, Leisure City
This modern pool house is located in Homestead, Florida, just 3.8 km from the Florida Keys Factory Shops and 5.3 km from Fruit Spice Park, offering a convenient base for exploring the Everglades and Keys. The house is ideal for large groups, with a spacious 1000 square metre layout and a guest capacity of 19.
The house features a private pool and terrace, a modern design with a fully equipped kitchen and comfortable living space, a shared kitchen and lounge, free parking, a washing machine, and an outdoor dining area.
Reel Escape 2: Charming 2nd Floor Condo In Marathon, Dock, Ramp, Shared Pool & Close To Everything! - Florida Keys, FL
9.8 19 reviews

Reel Escape 2: Charming 2nd Floor Condo In Marathon, Dock, Ramp, Shared Pool & Close To Everything!

apartment, Marathon
This Marathon condo is situated less than 1.6km from Coco Plum Beach and Curry Hammock State Park, and under 3.2km from the Marathon Visitor Centre and San Pablo Catholic Church.
This 56 square metre self-catering apartment sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, a private balcony, and access to a swimming pool and barbecue facilities.
Snorkel & Dive Legendary Coral Reefs - Then Relax Poolside With A Drink! - Florida Keys, FL
9.9 178 reviews

Snorkel & Dive Legendary Coral Reefs - Then Relax Poolside With A Drink!

apartment, Tavernier
This waterfront apartment is located in Tavernier, within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful escape close to local attractions. The property has consistently received excellent ratings for cleanliness, location, and user experience, ensuring a comfortable stay.
The apartment spans 88 square metres and comfortably accommodates up to four guests in two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, tennis court, and a private balcony, perfect for relaxing and enjoying the Florida Keys lifestyle.

Best Florida Keys, FL holiday rentals with parking

Lime Tree Bay Resort - Florida Keys, FL
8.9 5192 reviews

Lime Tree Bay Resort

resort, Layton
Lime Tree Bay Resort is situated on a private beach on Long Key, a beautiful island located between Islamorada and Marathon, just over 100km south of Miami. The resort receives very good ratings for its location, cleanliness, and overall user experience.
The resort offers a variety of accommodation options, all featuring flat-screen TVs, Wi-Fi, microwaves, and refrigerators. Guests can enjoy a range of amenities and activities, including two swimming pools, a private beach, a fishing dock, a restaurant, a bar, a spa, a fitness centre, and tennis courts.
Gorgeous Lagoon-front 2br Townhouse With 2 Pools - Florida Keys, FL
9.8 167 reviews

Gorgeous Lagoon-front 2br Townhouse With 2 Pools

apartment, Key Largo
This yacht is located in a community just outside John Pennekamp Coral Reef State Park, offering easy access to the park's renowned snorkeling and diving spots. The property has received excellent ratings for its location, cleanliness and overall user experience.
The yacht has two bedrooms and two bathrooms, comfortably accommodating up to five guests. It comes equipped with a kitchen, air conditioning, a swimming pool, and internet access, as well as two bicycles and two kayaks for exploring the area.
Ocean Community, Perfect Condo - Florida Keys, FL
10 15 reviews

Ocean Community, Perfect Condo

apartment, Marathon
This one-bedroom flat is located within the secure Ocean Isles Fishing Village in Marathon, providing direct oceanfront access and proximity to the Florida Keys' natural attractions.
This apartment offers a full kitchen, in-unit laundry, a queen sleeper sofa, and access to 7 acres of oceanfront amenities, including a heated swimming pool and fishing pier, with capacity for four guests.
Aqua Lodge Houseboat "Sea Turtle" - Florida Keys, FL
9.3 44 reviews

Aqua Lodge Houseboat "Sea Turtle"

houseboat, Tavernier
This houseboat is situated in Tavernier, a short walk from Baker's Cay Resort Beach and Mariners Hospital, offering a peaceful escape from the hustle and bustle of everyday life. The property has excellent user, location, and cleanliness ratings, indicating a high-quality experience. This floating home features one bedroom and one bathroom, accommodating up to two guests. Amenities include a private pool, a terrace, and a garden, as well as internet access, air conditioning, and a kitchen with a fridge and microwave.
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