Holiday 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

Waterfront Luxury Villa 19 With Sunset Views And Boat Slip Townhouse - Florida Keys, FL
9.8 30 reviews

Waterfront Luxury Villa 19 With Sunset Views And Boat Slip Townhouse

house, Marathon
This waterfront townhouse in Marathon, Florida Keys, is located an 8-minute walk from the Florida Keys Aquarium Encounters and a 17-minute walk (approximately 1.36km) from Captain Hook's Marina Dive Center, within 16km of the Seven Mile Bridge.
The three-bedroom property offers free Wi-Fi, private parking, a private boat slip, swimming pool, fitness centre, and a fully equipped kitchen including a dishwasher; it sleeps families or groups and is close to cycling routes.
Florida Keys Townhouse For Rent 2/2 - Florida Keys, FL
9.4 181 reviews

Florida Keys Townhouse For Rent 2/2

apartment, Key Largo
This family-friendly house is located in Key Largo, just 1.6 kilometres from Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, making it ideal for exploring the area's attractions. It has consistently received excellent ratings from previous guests.
This two-bedroom house is 93 square metres and can accommodate up to five guests. It offers a range of amenities, including a swimming pool, a tennis court, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Indigo Reef #17~ Plane Fun ~ 31' Boat Slip! - Florida Keys, FL
9.6 13 reviews

Indigo Reef #17~ Plane Fun ~ 31' Boat Slip!

apartment, Marathon
This three-bedroom townhouse is situated in Marathon Shores, a quiet neighbourhood in Marathon, Florida, within easy reach of Captain Hooks Marina and Dive Center, Florida Keys Country Club, Sombrero Beach and the public tennis courts. The property has received excellent ratings for its location, cleanliness and overall user experience.
The townhouse is spacious, with 149 square metres of floor area and a capacity for eight guests. It offers a range of amenities to make your stay comfortable and enjoyable, including a private pool, a fully equipped kitchen, a terrace, a garden, a spa and a fitness centre.
Tropical 2br2ba Getaway In Gorgeous Key Largo, Marina, Saltwater Lagoon, Pool - Florida Keys, FL
10 3 reviews

Tropical 2br2ba Getaway In Gorgeous Key Largo, Marina, Saltwater Lagoon, Pool

house, Key Largo
This beachfront Key Largo property offers direct access to a marina and saltwater lagoon, situated along the coast for an ideal waterside getaway.
This 85 square meter villa accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a swimming pool, a terrace, garden, tennis court, barbecue facilities, and Wi-Fi.

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

(#1)beautiful 4 Bed 3 Bath Pool Home W Dock Slip - Florida Keys, FL
9.7 343 reviews

(#1)beautiful 4 Bed 3 Bath Pool Home W Dock Slip

apartment, Marathon
This family-friendly house is located in Marathon, just 1.6 kilometres from Fishermen's Community Hospital and Vaca Key, and 4.8 kilometres from Crane Point Museum and Nature Center and Pigeon Key Foundation, offering a peaceful and relaxing environment. The house has received excellent ratings for user experience, location, and cleanliness.
This spacious house offers four bedrooms and a sofa bed, accommodating a large family or group of friends. The property features a private swimming pool, a terrace, a garden, a bar, and parking, as well as modern amenities such as a fully equipped kitchen, air conditioning, and free Wi-Fi.
Waterfront Home, Pool, Dock & Hot Tub-3min Beach - Florida Keys, FL
9.7 42 reviews

Waterfront Home, Pool, Dock & Hot Tub-3min Beach

apartment, Marathon
This waterfront holiday home is located in Marathon, just five kilometres from Sombrero Beach by boat, offering a peaceful escape with direct ocean access and a private canal dock. It has been consistently rated excellent for location, cleanliness and user experience.
The property boasts three bedrooms and three bathrooms, comfortably accommodating up to six guests. It's fully equipped with a kitchen, air conditioning, a garden, a washing machine and dryer, and outdoor amenities such as a canal deck, a refrigerator and freezer, and two kayaks, allowing for fishing, kayaking and enjoying the Florida Keys weather.
Tropical Seahorse At Coral Lagoon ~ Waterfront Villa W Resort Pool - Florida Keys, FL
9.2 116 reviews

Tropical Seahorse At Coral Lagoon ~ Waterfront Villa W Resort Pool

apartment, Marathon
This three-bedroom villa is situated in Coral Lagoon Resort, just next to Key Colony Beach in Marathon, Florida, a short drive from the Seven Mile Bridge and around 50 miles from Key West. It has consistently received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The 133 square metre property comfortably accommodates eight guests with its three bedrooms and two and a half bathrooms. Guests can enjoy a range of amenities including a private pool, a fully equipped kitchen, and a spacious terrace with stunning canal views, making it perfect for relaxing and enjoying the tropical ambiance.
Matecumbe Resort - Florida Keys, FL
8.7 551 reviews

Matecumbe Resort

aparthotel, Islamorada, Village of Islands
The Matecumbe Resort is situated in Islamorada, a short distance from Sea Oats Beach, Upper Matecumbe Key, and Windley Key, offering a convenient base to explore the beautiful Florida Keys. This 2-star aparthotel consistently receives very good user ratings for its cleanliness, location, and overall experience.
Each self-catering apartment comes equipped with a kitchen, including a fridge, microwave, and other essentials. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden, free parking, and Wi-Fi, as well as access to a private beach.

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 captivating sunset celebrations at Mallory Square. Further up the Keys, you'll find the stunning Seven Mile Bridge, offering breathtaking views, and the John Pennekamp Coral Reef State Park, perfect for snorkelling or diving amongst vibrant coral reefs. Don't miss the historic architecture and charming shops of Key Largo.
  • 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 unique coral reef ecosystem, the only living coral barrier reef in the continental United States. Witnessing the diverse marine life is a truly special experience. The area also experiences spectacular sunsets, particularly in Key West, and boasts various bird species, including the occasional sighting of migratory birds.
  • 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!), a hat, sunglasses, and insect repellent. Comfortable walking shoes are a must, especially if you plan on exploring the many islands. Don't forget your camera to capture the stunning scenery and marine life. If you plan on water activities, bring appropriate gear.
  • 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, a colourful and quirky celebration, is a highlight. The annual Key West Conch Republic Independence Celebration is another popular event, showcasing the local culture and spirit. Many smaller festivals and events are held throughout the Keys, often celebrating local seafood or arts and crafts.
  • 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 many excellent restaurants. In Key West, Louie's Backyard is a popular choice, known for its fresh seafood and stunning waterfront views. Further up the Keys, you'll find many smaller, family-run establishments serving delicious Key lime pie (a must-try!), fresh seafood, and conch fritters. Local seafood is always a great option, reflecting the area's bounty.
  • 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?

    Beyond the well-known spots, consider visiting the Bahia Honda State Park, known for its beautiful beaches and historic bridge. The Crane Point Museum in Marathon offers insights into the natural and cultural history of the region. Exploring the backcountry roads and discovering hidden coves and beaches can also be a rewarding experience.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?

    Visiting local markets and interacting with vendors is a great way to engage with the community. Attending smaller local events or festivals offers a chance to experience the Keys' unique culture firsthand. Simply striking up conversations with people you meet – whether in a restaurant, shop, or on the beach – can provide valuable insights.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, FL, United States?

    The Florida Keys are renowned for their unique landscape. The islands themselves are low-lying, with mangrove forests, beaches, and the iconic coral reef system. Exploring the diverse habitats, from the shallow waters to the deeper ocean, reveals a fascinating array of natural beauty.
  • 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 Key Largo, and a couple of days exploring the middle Keys, visiting Marathon and Islamorada. This allows for relaxation and exploration of the various islands and their offerings. Shorter trips are possible, focusing on specific areas of interest.

Nearby regions

Best Florida Keys, FL holiday rentals with a balcony

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq - Florida Keys, FL
9.9 335 reviews

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq

apartment, Tavernier
This two-bedroom apartment is situated in the Ocean Pointe Suites gated resort community in Tavernier, directly on the Atlantic Ocean, just minutes from Tavernier Creek, offering direct access to both the bay and the ocean. It has received excellent ratings for its location, cleanliness, and overall experience.
The 78 square metre property comfortably accommodates up to six guests, with two bathrooms and a queen-size Murphy bed in the living room. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, parking, and internet access, as well as access to the resort's private beach, tennis courts, and waterfront café.
Deja Blue Oceanfront Condo- 2 Lanais, Pool + Beach - Florida Keys, FL
9.8 177 reviews

Deja Blue Oceanfront Condo- 2 Lanais, Pool + Beach

apartment, Tavernier
This waterfront apartment in Tavernier is conveniently located just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment features two bedrooms and two bathrooms, spanning 91 square metres and comfortably accommodating up to six guests. Enjoy a range of amenities including a swimming pool, jacuzzi, tennis court, barbecue grills, and a fully equipped kitchen, all set within a beautiful garden area.
P64 - Spacious 3 Bedroom Duplex In Key Colony With Dockage And Cabana Club Access! - Florida Keys, FL
9.5 40 reviews

P64 - Spacious 3 Bedroom Duplex In Key Colony With Dockage And Cabana Club Access!

apartment, Key Colony Beach
This Key Colony Beach waterfront property offers stunning views and direct access to the water, situated within 3.2km of Sunset Park Beach, the Marathon Visitor Centre, and Curry Hammock State Park.
Sleeping eight guests, this two-bathroom house boasts a private pool, fully equipped kitchen, free Wi-Fi, barbecue grills, and a balcony, perfect for families or groups seeking a relaxing Key Colony Beach getaway.
Spacious Canal-front Home With Balcony - Monthly Rental - Florida Keys, FL
No reviews

Spacious Canal-front Home With Balcony - Monthly Rental

apartment, Key Largo
This canal-front flat in Sunrise Point, Key Largo, is located 2.4 kilometres from the Florida Keys Wild Bird Rehabilitation Centre, 8 kilometres from John Pennekamp Coral Reef State Park, and 8 kilometres from downtown Key Largo's amenities.
This family-friendly accommodation offers 82 square metres of space for up to four guests, featuring air conditioning, a kitchen with a fridge and microwave, a balcony with water views, and convenient parking, with opportunities for jet skiing, kayaking, and ecotours nearby.

Best Florida Keys, FL holiday rentals with parking

Prime Time 2: Charming Canal Front Duplex, Your Gateway To South Pine Channel & Atlantic/gulf Waters - Florida Keys, FL
9.3 11 reviews

Prime Time 2: Charming Canal Front Duplex, Your Gateway To South Pine Channel & Atlantic/gulf Waters

apartment, Big Pine Key
This holiday home is located in Pine Channel Estates, just 1.6 km from the Big Pine Key Flea Market and the National Key Deer Refuge Visitor Center, and within a 5 km radius of Coupon Bight Aquatic Preserve and the Key West Visitors Center, offering a peaceful and secluded setting. The property has received excellent user and location ratings, and a very good cleanliness rating.
The 101 square metre house has two bedrooms, one bathroom, and can accommodate up to six guests. It features a fully equipped kitchen, a garden, parking, internet, air conditioning, and gas grills for outdoor cooking.
Ocean View Corner Penthouse Ocean Pointe 5416 - Florida Keys, FL
9.9 191 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

apartment, Tavernier
This penthouse apartment is located in Ocean Pointe Suites, midway between Key Largo and Islamorada in the Florida Keys, offering easy access to both locations, approximately 80km from each. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. Amenities include a private beach, pier, marina, swimming pool, jacuzzi, tennis and pickleball courts, and a basketball hoop. Guests can also enjoy direct ocean views from the balcony and living area, and access to a range of water activities such as fishing, diving, snorkeling, paddleboarding, and kayaking.
Oceanside, Pet Friendly, Smart Home With-sup, Kayak With And 60 Ft Dock - Florida Keys, FL
9.9 104 reviews

Oceanside, Pet Friendly, Smart Home With-sup, Kayak With And 60 Ft Dock

apartment, Marathon
This oceanfront property in Marathon, Florida Keys, is situated 2.9km from Captain Hook's Marina Dive Centre and 1.3km from Florida Keys Aquarium Encounters, offering easy access to local attractions.
This 96 square metre house boasts two bedrooms, two bathrooms, a fully equipped kitchen with barbecue, and includes paddleboards and kayaks for guests' use; it comfortably sleeps a family and pets are welcome.
Waterfront 2br/2ba Condo W/ Boat Slip, Private Ramp & Chilled/heated Pool - Florida Keys, FL
10 11 reviews

Waterfront 2br/2ba Condo W/ Boat Slip, Private Ramp & Chilled/heated Pool

apartment, Marathon
This waterfront condominium in Marathon offers immediate access to the water via a private boat slip and ramp, situated a short walk from Cocoplum Beach.
This 2-bedroom, 2-bathroom flat accommodates up to 6 guests and features a fully stocked kitchen, a separate coffee/breakfast bar, shared pool and tiki areas, a bait freezer, and a fish cleaning station, with jet skiing, kayaking, and scuba diving opportunities nearby.
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