Florida Keys Short term rentals

11096 available short term rental offers

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Florida Keys short term rentals
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Best Short term and Weekly rentals in Florida Keys

Best family friendly Florida Keys Short term rentals

Among the 11096 accommodations in Florida Keys, here are the 4 best family friendly rentals

Waterfront W/270 Degree Views, Cabana Club, Multiple Docks - Florida Keys
9.7 241 reviews

Waterfront W/270 Degree Views, Cabana Club, Multiple Docks

apartment, Key Colony Beach
This two-bedroom duplex apartment is located at the end of the causeway in Key Colony Beach, offering stunning views of the bay and easy access to the Cabana Beach Club within a short walk. The apartment has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The 97 square metre apartment can comfortably accommodate up to five guests and features a fully equipped kitchen, two bathrooms, and a spacious living area. Guests can enjoy a range of amenities including a private swimming pool, a jacuzzi, a garden, a spa, and parking for one trailer.
Luxury Family Retreat W/heatedpool, Sports Fields - Florida Keys
10 14 reviews

Luxury Family Retreat W/heatedpool, Sports Fields

apartment, Florida City
This Florida City residence offers excellent access to natural attractions, being just 1600 metres to 2400 metres from Everglades National Park and 2400 metres to 3200 metres from Biscayne National Park, with Miami's beaches approximately 64000 metres to 80000 metres away.
This expansive 210 square metre dwelling, ideal for up to 14 guests, features a resort-style garden with a private swimming pool, spa, soccer pitch, beach volleyball court, and mini golf, alongside indoor entertainment options and a children's playground.
Waterfront Cabana 2 Key Largo - Florida Keys
9.2 27 reviews

Waterfront Cabana 2 Key Largo

apartment, Key Largo
Waterfront Cabana 2 Key Largo is situated 7.2 kilometres from John Pennekamp Coral Reef State Park and 7.4 kilometres from Dolphin Cove, offering convenient access to Key Largo's attractions.
This recently renovated one-bedroom apartment, measuring 39 square metres, sleeps four guests and features a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, private parking, and a garden.
Stunning Luxury Backyard Retreat - Florida Keys
No reviews

Stunning Luxury Backyard Retreat

apartment, South Miami Heights
This Richmond West flat is located 13.6 kilometres from Fruit Spice Park and 19.3 kilometres from Homestead Air Force Base, offering a South Miami Heights retreat.
This one-bedroom flat accommodates up to eleven guests and features a private swimming pool, a fully equipped kitchen, air conditioning, and free WiFi and parking.

Best Florida Keys short term 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.
Duval House - Florida Keys
9.2 1819 reviews

Duval House

B&B, Key West
Duval House is located on Duval Street, just a short walk from the Ernest Hemingway Home and Museum and the Southernmost Point, putting you right in the heart of Key West's lively atmosphere. The guesthouse has received very good ratings for its cleanliness, location and overall experience.
Duval House consists of seven buildings with a distinct Caribbean style. The guesthouse offers a range of amenities, including a swimming pool, a garden, a terrace, free Wi-Fi, parking, and a continental breakfast.
Florida Keys Townhouse For Rent 2/2 - Florida Keys
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.
Kayaks, Hot Tub, Dock, Cabana Club - Florida Keys
9.7 53 reviews

Kayaks, Hot Tub, Dock, Cabana Club

apartment, Key Colony Beach
This canal-front apartment in Key Colony Beach is located a short distance from Captain Hooks Marina and Dive Center and Florida Keys Country Club, offering easy access to a variety of activities and attractions. The property has received excellent ratings for user experience, location, and cleanliness.
The apartment spans 117 square metres and comfortably sleeps six guests. It features a fully equipped kitchen, a spacious living room with a queen pull-out sofa, a private balcony overlooking the canal, and a private dock with deep water access.

Frequently asked questions about short term rentals in Florida Keys

  • What attractions should one visit during a week-long stay in the Florida Keys?

    A week in the Keys allows for a good overview. Start in Key Largo, exploring John Pennekamp Coral Reef State Park for snorkelling or diving. Head down to Islamorada, known as the 'Sport Fishing Capital of the World', and visit the History of Diving Museum. Key West is a must-see, with the Ernest Hemingway Home and Museum, Mallory Square for the sunset celebration, and Duval Street for its vibrant atmosphere. Consider a day trip to Dry Tortugas National Park for its stunning fort and coral reefs, accessible by ferry.
  • What are the best short term rentals in Florida Keys?

    Among the short term rentals in Florida Keys, Relaxed Boho Vibes & Views [ Ocean Pointe 2315], At Mine | Lovely Suite Steps From Duval Street and Getaway In The Everglades are the most popular ones.

  • What attractions should one visit when spending a month in the Florida Keys?

    A month gives you time to truly explore. Besides the highlights mentioned above, consider exploring the less-visited Keys. Spend time kayaking or paddleboarding through the mangroves in Bahia Honda State Park. Visit the African Queen, the boat from the Humphrey Bogart film, in Key Largo. Explore the backcountry roads, discovering hidden beaches and charming smaller towns. Take a boat trip to explore the backcountry, or visit the numerous smaller museums and art galleries throughout the Keys. Consider visiting the Looe Key National Marine Sanctuary for some excellent diving or snorkeling.
  • What are the best short term rentals with a pool in Florida Keys?

  • Can visitors to the Florida Keys witness any unique natural cycles, like cherry blossom season or autumn colours?

    The Florida Keys don't experience autumn colours in the same way as further north. The subtropical climate means the foliage remains largely evergreen. There's no cherry blossom season either. However, you can witness vibrant blooms of tropical flowers throughout the year, and the changing tides and marine life offer their own natural cycles to observe.
  • What are the best short term rentals with a jacuzzi in Florida Keys?

    The best short term rentals with a jacuzzi in Florida Keys are Relaxed Boho Vibes & Views [ Ocean Pointe 2315], Waterfront Cabana 6 and Coco Plum Beach & Tennis Club & Marina.

  • What are the most meaningful ways to engage with locals and discover the culture in the Florida Keys?

    To engage with the local culture, visit local restaurants and bars away from the main tourist areas. Chat with the staff at smaller businesses, like the local art galleries and fishing supply shops. Attend local events – check community calendars for festivals and gatherings. Consider taking a guided tour focused on the history and culture of the Keys, possibly a walking tour in Key West or a boat tour focused on the local ecology.
  • What are the best short term rentals for families and kids in Florida Keys?

  • Are there any distinctive cultural activities or hands-on workshops in the Florida Keys?

    Yes, there are. Many art galleries offer workshops in painting, pottery, or glassblowing. Several locations offer conch shell crafting workshops, reflecting a traditional Key West craft. Fishing charters are common, offering hands-on experiences. There are also opportunities to learn about local ecology and conservation through guided tours and workshops.
  • What are some secret spots or hidden treasures to visit in the Florida Keys?

    Some lesser-known spots include the mangrove tunnels accessible by kayak in Key Largo, the quiet beaches of Bahia Honda State Park, and the historic lighthouse at the southernmost point of the US. Exploring the backcountry roads on a bicycle can lead to secluded beaches and breathtaking views. Many smaller, family-run restaurants offer authentic Key West cuisine.
  • What should not be left out of your suitcase if you are going to the Florida Keys?

    Pack light, breathable clothing suitable for warm weather. Sunscreen is essential, as is a hat and sunglasses. Swimwear is a must, along with water shoes for exploring beaches and coral reefs. Insect repellent is recommended, especially for evenings. Don't forget a reusable water bottle to stay hydrated in the tropical climate.
  • What are the most popular festivals in the Florida Keys?

    The Fantasy Fest in Key West is a well-known, ten-day costumed celebration in October. Key West also hosts the annual Hemingway Days celebration, honouring the famous author. Smaller, local festivals occur throughout the year celebrating art, food, and local culture – check local listings closer to your travel dates.
  • Where should one try the best local food in the Florida Keys?

    For the best Key Lime Pie, head to Kermit's Key West Key Lime Shoppe in Key West. Many restaurants throughout the Keys serve fresh seafood, a staple of the local cuisine. Look for smaller, family-run restaurants away from the main tourist areas for a more authentic experience. Try the local conch fritters, a Keys specialty.

Nearby regions

Best Florida Keys short term rentals with a kitchen

Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters! - Florida Keys
9.9 195 reviews

Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters!

apartment, Tavernier
This Tavernier apartment is directly on the beach, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, suitable for up to four guests. Amenities include a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, and parking.
Luxury 4br | Heated Pool + Mini Golf | Sleeps 11 - Florida Keys
9.9 36 reviews

Luxury 4br | Heated Pool + Mini Golf | Sleeps 11

apartment, Goulds
This new four-bedroom, three-bathroom residence is situated in Goulds, providing straightforward access to Miami's attractions and the Florida Keys, with the nearest shops located 2.5 kilometres away.
This modern apartment sleeps up to eleven guests and features a chef's kitchen, air conditioning, a private swimming pool, and driveway parking for four vehicles, making it ideal for families and groups seeking a comfortable stay.
Landing Amazing 3bd Pool Gym - Florida Keys
10 1 review

Landing Amazing 3bd Pool Gym

apartment, Naranja
This Naranja flat is located 8.9 kilometres from Fruit Spice Park, 9.8 kilometres from Homestead Air Force Base, and 10.3 kilometres from Homestead Miami Speedway.
This pet-friendly apartment offers air conditioning, free Wi-Fi, a fully equipped kitchen with a fridge, a private bathroom with a bath, and access to a pool and gym, with check-out at 10:00 AM.
Save Big $$$ Aug/sept. Oceanfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds - Florida Keys
9.6 415 reviews

Save Big $$$ Aug/sept. Oceanfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds

apartment, Cudjoe Key
This property is situated in Summerland Key, just a 10-minute walk from Venture Key, Venture Out Keys, and Out Key, with Upper Sugarloaf Key and Florida Keys Beaches within a 10-kilometre radius. This well-rated accommodation has received excellent reviews for its location, cleanliness, and overall experience.
The house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a swimming pool, a jacuzzi, a garden, a sauna, a fully equipped kitchen, and a parking space, ensuring a comfortable and enjoyable stay.

Best Florida Keys short term rentals with laundry available

Coconut Condo 2 Bed,  2 Bath Condo W/ Pool, Dockage, Trailer Parking & Boat Ramp - Florida Keys
9.0 42 reviews

Coconut Condo 2 Bed, 2 Bath Condo W/ Pool, Dockage, Trailer Parking & Boat Ramp

apartment, Marathon
This two-bedroom, one-and-a-half-bathroom condominium is situated in Marathon's Coco Plum district, offering convenient waterfront proximity and less than 60 metres' walk to a wide canal with boat dockage and ramp privileges, placing it near the Marathon Air Museum and Crane Point Museum and Nature Centre.
This well-appointed holiday flat accommodates up to six guests and features a shared swimming pool, air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, and is ideal for enjoying nearby water sports.
Tequila Sunrise - Florida Keys
10 107 reviews

Tequila Sunrise

apartment, Tavernier
This beachfront apartment in Tavernier, Florida Keys, at mile marker 92, offers direct ocean views and is a two-minute walk from the beach and marina, and within 1.6km of shops and restaurants, near Founders Park.
The two-bedroom, two-bathroom condo sleeps six, boasting a king-size and queen-size bed plus a queen sleeper sofa, a modern coastal décor, and access to a heated pool, jacuzzi, tennis/pickleball courts, BBQ area, and private beach within the gated resort; numerous extra amenities are provided.
Cottage 30 Min From Key West, Free Parking, Pool - Florida Keys
9.7 126 reviews

Cottage 30 Min From Key West, Free Parking, Pool

cottage, Big Pine Key
This Big Pine Key tiny house, part of Breezy RV Estates, offers a pet-friendly, family-suitable stay with convenient access to community amenities, though precise distances to Big Pine Key landmarks are unavailable.
The 500 sq ft (approximately 46 sq m) self-catering cottage sleeps four in one bedroom with three beds, featuring a full kitchen (fridge, freezer, microwave, oven, coffee maker, toaster, kettle), air conditioning, and access to a swimming pool and laundry facilities.
Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-pool - Florida Keys
9.8 113 reviews

Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-pool

apartment, Islamorada, Village of Islands
This two-bedroom apartment is located in the Anglers Reef community in Islamorada, just a short distance from local shops, bars, and restaurants, and within easy reach of the famous Islamorada "sandbar" and Alligator Reef. The apartment has received excellent ratings from previous guests and offers a peaceful, gated oasis with minimal traffic and stunning ocean views.
The 128 square metre apartment can accommodate up to six guests and features a spacious open layout, granite countertops, updated appliances, and a comfortable king-size bed in the master bedroom. Guests can enjoy a range of amenities, including a private swimming pool, boat docks, private beaches, three flat-screen TVs with Hulu and Netflix, complimentary wireless internet, a Keurig coffee pot, a full-size washer and dryer, and a fully equipped kitchen.
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