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

Best family friendly Florida Keys, FL Short term rentals

Among the 8594 accommodations in Florida Keys, FL, here are the 4 best family friendly rentals

Waterfront Cabana 1 Key Largo - Florida Keys, FL
9.2 14 reviews
Florida Keys, FL
07/31 – 08/03
$329/nighttotal: $987 (3 )

Waterfront Cabana 1 Key Largo

1 2
apartment , Key Largo
Waterfront Cabana 1 in Key Largo offers a direct waterfront location, just 4.5 miles from John Pennekamp Coral Reef State Park and 4.6 miles from Dolphin Cove.
This recently renovated 420-square-foot condo features one bedroom, one bathroom, and accommodates up to four guests, boasting a fully equipped kitchen, private patio, free Wi-Fi, and free parking.
Convenient Central Marathon Location, Canal View. - Florida Keys, FL
9.6 53 reviews
Florida Keys, FL
06/20 – 06/27
$216/nighttotal: $1512 (7 )

Convenient Central Marathon Location, Canal View.

1 2
apartment , Marathon
This Marathon Shores vacation home is located within a 10-minute walk of Captain Hooks Marina and Dive Center, Coco Plum Beach, and San Pablo Catholic Church. The one-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen, a barbecue grill, a terrace, and a garden.
Charming & Tranquil Condo At Ocean Pointe-sleeps 6 - Florida Keys, FL
10 81 reviews
Florida Keys, FL
06/20 – 06/27
$441/nighttotal: $3087 (7 )

Charming & Tranquil Condo At Ocean Pointe-sleeps 6

2 5
apartment , Tavernier
This family-friendly condo is located in Tavernier, just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's natural beauty. It has received excellent user ratings, making it a popular choice for travelers. This two-bedroom, two-bathroom rental with a sofa bed comfortably sleeps six guests. Enjoy the private pool, tennis court, BBQ grills, and other amenities while taking advantage of the free WiFi and convenient location.
Welcome To Paradise! - Florida Keys, FL
9.6 86 reviews
Florida Keys, FL
07/31 – 08/03
$316/nighttotal: $948 (3 )

Welcome To Paradise!

1 2
apartment , Key Largo
This oceanfront Key Largo apartment is located in the gated Kawama Yacht Club community, just a short walk from the beach and close to John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park. This highly-rated rental receives excellent reviews from previous guests.
The apartment is a one-bedroom, one-bathroom unit with a 900 square foot floor plan that comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private balcony overlooking a nature preserve, access to a resort-style community with multiple swimming pools, a saltwater lagoon, tennis courts, a fishing jetty, and a playground.

Best Florida Keys, FL lodging with a balcony

Apartment ∙ 7 Bedrooms ∙ 19 Guests - Florida Keys, FL
Florida Keys, FL
07/24 – 07/27
$4027/nighttotal: $12081 (3 )

Apartment ∙ 7 Bedrooms ∙ 19 Guests

7 14
apartment , Key West
Banana's Foster Guest House, located on the corner of Caroline and Simonton Streets in Key West's historic Old Town, offers easy access to Duval Street and Mallory Square.
This seven-bedroom, seven-bathroom Key West vacation rental sleeps up to 19 guests in six private units with kitchenettes or full kitchens, a private pool, and parking for four vehicles; pet-friendly (up to 40 lbs, $15/night per pet, max 2).
Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar - Florida Keys, FL
9.7 127 reviews
Florida Keys, FL
11/25 – 11/27
$486/nighttotal: $972 (2 )

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

2 6
apartment , Tavernier
This waterfront condo in Tavernier offers stunning views and is within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park. With excellent user, location, and cleanliness ratings, this apartment is a great choice for travelers.
The apartment has two bedrooms, two bathrooms, and a floor area of 940 square feet, accommodating up to six guests. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a jacuzzi, a terrace or balcony, a garden, a spa, a tennis court, and parking.
Bright & Sunny Suite W/ Magnificent Ocean Views - Florida Keys, FL
9.8 102 reviews
Florida Keys, FL
06/19 – 06/23
$456/nighttotal: $1824 (4 )

Bright & Sunny Suite W/ Magnificent Ocean Views

2 4
apartment , Tavernier
This Tavernier condo is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to waterfront activities and local attractions. This rental has received excellent user ratings, making it a popular choice for travelers.
This two-bedroom, two-bathroom apartment comfortably sleeps six guests and spans 900 square feet. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, and access to a water park.
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina - Florida Keys, FL
9.9 285 reviews
Florida Keys, FL
11/25 – 11/27
$536/nighttotal: $1072 (2 )

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

2 6
apartment , Tavernier
This oceanfront condo is located in the gated Ocean Pointe resort community in Tavernier, just a short distance from Tavernier Creek and offers direct bay or ocean access. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom, two-bathroom vacation rental spans 850 square feet and comfortably accommodates up to six guests. The property features a fully equipped kitchen, a private terrace, a swimming pool, a jacuzzi, and a fitness center, along with convenient access to a variety of activities and attractions in the area.

Frequently Asked Questions about short term rentals in Florida Keys, FL

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

    A week in the Florida Keys offers a taste of its diverse offerings. Start in Key Largo, exploring John Pennekamp Coral Reef State Park for snorkeling or diving. Head down to Islamorada, known as the "Sport Fishing Capital of the World," and maybe try a fishing charter. Key West is a must-see, with its iconic Southernmost Point Buoy, Ernest Hemingway Home and Museum, and the vibrant Duval Street. Consider a sunset celebration at Mallory Square. Don't forget to enjoy the beaches along the way, like Bahia Honda State Park, known for its beautiful bridges and calm waters.
  • What are the best short term rentals in Florida Keys, FL?

    Among the short term rentals in Florida Keys, FL, Secret Courtyard Cottage, At Mine | Lovely Suite Steps From Duval Street and Spacious - Private 1 Bed/1 Bath Apt In Everglades are the most popular ones.

  • What types of short-term rentals are available in the Florida Keys?

    If you are looking for accommodations in the Florida Keys you can book short-term rentals which can make a huge difference. The best part about these short-term rentals is that they come in different forms and sizes. Hence, you can choose from different apartments, condos and even townhouses. Also, you can decide what size you prefer for your holidays. If you are with your partner you can choose smaller studio apartments while you can choose bigger condos for a family holiday trip. This would allow you to make the best use of the space available without having to book a hotel room. You can also look for properties that come furnished with all modern bathroom and kitchen facilities and amenities.
  • What attractions should you visit when you spend a month in the Florida Keys?

    A month gives you time for a deeper exploration. Beyond the popular spots, consider visiting the smaller islands and exploring their unique character. Spend time kayaking or paddleboarding through the mangroves. Explore the backcountry on a boat tour, discovering hidden coves and wildlife. Visit the History of Diving Museum in Islamorada. Take a day trip to Dry Tortugas National Park, a remote island with a historic fort and pristine coral reefs. Enjoy the many restaurants and local shops throughout the Keys, from Key Largo to Key West.
  • What are the best short term rentals with a pool in Florida Keys, FL?

  • What are the best kid-friendly attractions in the Florida Keys?

    1. Founders Park - Located in Islamorada, Founders Park is a great place where kids can enjoy 45 acres of fun and water activities. Here adults and kids can spend time in a splash park, play tennis, basketball and explore various walking trails.
    2. Key West Aquarium - Also, when you are exploring the Florida Keys you can visit the Key West Aquarium where you can take the kids to knowing more about marine life in their natural habitat.
    3. Calusa Beach - One of the family-friendly beaches in Florida Keys you can take kids here for an adventurous family beach day experience.
  • Can visitors to the Florida Keys witness any unique natural cycles, like cherry blossom season or autumn colors?

    No, the Florida Keys' subtropical climate doesn't experience the dramatic seasonal changes seen further north. You won't find cherry blossoms or vibrant autumn foliage. The Keys offer a more consistent, warm climate year-round, with variations in water temperature and the occasional tropical storm.
  • What are the best short term rentals with a jacuzzi in Florida Keys, FL?

    The best short term rentals with a jacuzzi in Florida Keys, FL are Secret Courtyard Cottage, Marco Beach Ocean Suites and Coco Plum Beach & Tennis Club & Marina.

  • What's the best neighbourhood to stay close to the city centre?

    If you are planning to visit the Florida Keys you can plan to stay in Key West which is probably the best place where you can find plenty of options and facilities. Choosing Key West allows you to explore several hotels and rental accommodations which can make things easier for you. Also, you can explore many beaches and local attractions which would allow you to stay close to them. You can always find plenty of dining and shopping options in Key West and that can make your holidays in Florida Keys better.
  • What are the most meaningful ways to engage with locals and discover the culture in the Florida Keys?

    To connect with the local culture, visit local restaurants and bars, like the Hogfish Bar & Grill in Islamorada, and strike up conversations. Attend a local event or festival. Explore the smaller, less touristy towns and villages. Visit art galleries showcasing local artists. Consider taking a guided tour focusing on the history and culture of the Keys. Many local businesses are family-owned and operated, offering a chance to interact with residents.
  • What are the best short term rentals for families and kids in Florida Keys, FL?

    The best short term rentals for families and kids in Florida Keys, FL are Secret Courtyard Cottage, Upper Bayview North: Waterfront 4 Bedroom Condo At Bayfront Suites & Marina and Marco Beach Ocean Suites.

  • What are the best shopping malls in the Florida Keys?

    1. Duval Square Mall - Located in Key West, Duval Square Mall is one of the best shopping places in the Florida Keys. Here you can enjoy shopping for hours and find dining options as well.
    2. Key Largo Shopping Center - If you are staying close to mainland Florida you would want to visit Key Largo Shopping Center where you can shop for hours and enjoy friendly services and delicious food.
    3. The Shops at Mallory Square - Mallory Square is one of the premier shopping destinations in Key West and this place can provide you with plenty of shops and boutiques for shopping.
  • Are there any distinctive cultural activities or hands-on workshops in the Florida Keys?

    Yes, several opportunities exist. Many art galleries offer workshops, particularly in Key West. Some resorts and local businesses offer conch shell crafting workshops. You can find opportunities for learning about local fishing techniques or even taking a class on becoming a certified diver. Check local listings for specific offerings during your visit.
  • What is the best place to book a short-term rental for the Key West Lobsterfest in the Florida Keys?

    If you are planning to attend Key West Lobsterfest in the Florida Keys you should book your short-term rental in Key West. This is one of the best towns where you can find plenty of rental accommodations. Hence, you need to evaluate and choose the best apartments and condos you can find here for your stay. These properties are fully furnished with all modern kitchen and bathroom facilities and amenities and therefore you can find the best deals here. Also, the festival happens in Key West and therefore you can stay close to the venue and explore other city attractions when you are done attending the event.
  • What are some secret spots or hidden treasures to visit in the Florida Keys?

    Some lesser-known gems include the mangrove tunnels accessible by kayak or paddleboard in various locations. Explore the quieter beaches away from the main tourist areas. Look for local fishing spots recommended by residents. Discover hidden bars and restaurants off the main streets. The best way to find these is by talking to locals and exploring beyond the well-trodden paths.
  • What should not be left out of your suitcase if you are going to the Florida Keys?

    Pack light clothing, swimwear, sunscreen (high SPF!), sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially if exploring mangrove areas. A reusable water bottle is essential due to the warm climate. If you plan on water activities, pack appropriate gear like snorkeling equipment or water shoes.
  • What are the most popular festivals in the Florida Keys?

    The Florida Keys boast several festivals throughout the year. Key West's Fantasy Fest is a renowned, large-scale costumed celebration held in October. The Conch Republic Independence Celebration in Key West is a quirky and fun event. Numerous smaller festivals and events, like art walks and music festivals, take place throughout the Keys; checking local event calendars closer to your travel dates is recommended.
  • Where should you try the best local food in the Florida Keys?

    The Florida Keys offer diverse culinary experiences. For fresh seafood, many restaurants along the waterfront provide excellent options. Try a local conch fritter or a Key lime pie. Explore smaller, family-run restaurants for authentic Key West cuisine. Look for restaurants featuring locally sourced ingredients. Each island has its own unique culinary scene, so exploring different locations provides a broader taste of the Keys' food.

Nearby regions

Best Florida Keys, FL lodging with a kitchen

Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!! - Florida Keys, FL
10 158 reviews
Florida Keys, FL
06/20 – 06/27
$436/nighttotal: $3052 (7 )

Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!!

2 5
apartment , Islamorada, Village of Islands
This waterfront apartment in Matecumbe, Islamorada, offers a unique 5-star experience with its private dock, heated pool, hot tub, and lighted tennis courts. It is highly rated by previous guests for its cleanliness, comfort, and amenities.
The apartment features 2 bedrooms, 3 bathrooms, and a floor area of 1700 square feet, comfortably accommodating up to 6 guests. It boasts a fully equipped kitchen, a spacious living area, and a private terrace overlooking the water. Guests can enjoy complimentary amenities such as bikes, pool toys, and a freezer for bait/catch, as well as access to a concierge service for assistance with activities and arrangements.
2br Coastal Retreat With Private Balcony, Pool - Florida Keys, FL
8.6 78 reviews
Florida Keys, FL
06/19 – 06/23
$247/nighttotal: $988 (4 )

2br Coastal Retreat With Private Balcony, Pool

1 4
apartment , Tavernier
This 2-bedroom, 2-bathroom apartment in Tavernier offers a coastal getaway with access to shared amenities like a swimming pool and tennis courts, situated within a mile of restaurants and shops such as Chad's Deli & Bakery and Sunrise Cuban Market & Cafe, and 10 miles from John Pennekamp Coral Reef State Park. Enjoy a private balcony with garden views, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and free WiFi, perfect for accommodating up to 4 guests for a beach vacation.
Penthouse Apartment Sunsets In Key Largo, Kawama Yacht Club Tower - Florida Keys, FL
9.9 193 reviews
Florida Keys, FL
07/26 – 08/01
$385/nighttotal: $2310 (6 )

Penthouse Apartment Sunsets In Key Largo, Kawama Yacht Club Tower

2 4
apartment , Key Largo
This Key Largo apartment is conveniently located near popular attractions like Baker's Cay Resort Beach, Jimmy Johnson's Big Chill, and Jacob's Aquatic Center, all within a 2-mile radius. This unit has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi.
Waterfront Townhome With Pool, Dock & Water Views - Florida Keys, FL
9.8 74 reviews
Florida Keys, FL
06/19 – 06/23
$449/nighttotal: $1796 (4 )

Waterfront Townhome With Pool, Dock & Water Views

3 4
apartment , Marathon
This Marathon vacation rental is located in the Coral Lagoon community, just an hour's drive from Key West and Key Largo. It's rated excellent by previous guests and offers a relaxing and convenient stay.
This 3-bedroom, 3-bathroom Key West style townhome can accommodate up to 6 guests. It includes a private dock, a heated pool, a fully equipped kitchen, a washer and dryer, and Smart TVs in each bedroom, along with a shaded outdoor seating area for entertaining.

Best Florida Keys, FL lodging with laundry available

Seas The Day In Cudjoe Key - Florida Keys, FL
8.7 45 reviews
Florida Keys, FL
06/19 – 06/23
$288/nighttotal: $1152 (4 )

Seas The Day In Cudjoe Key

2 4
apartment , Cudjoe Key
Seas The Day is a mobile home located on Cudjoe Key, a short drive from popular Key West attractions like Ernest Hemingway Home and Museum and Duval Street. This property has received excellent ratings for location, cleanliness, and user experience.
The mobile home features 2 bedrooms and 1 bathroom, providing comfortable accommodations for up to 4 guests. Enjoy amenities like a swimming pool, fitness center, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful surroundings.
Stay Near Jimmy Johnsons Big Chill  Just A 18-min Stroll Away - Florida Keys, FL
9.8 147 reviews
Florida Keys, FL
08/04 – 08/07
$480/nighttotal: $1440 (3 )

Stay Near Jimmy Johnsons Big Chill Just A 18-min Stroll Away

2 4
apartment , Key Largo
This Key Largo apartment is located near the ocean, within walking distance of Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, and within a short drive of Jacob's Aquatic Center and Bluefin Rock Harbor Marina. The property has been rated excellent for its location and user experience, and very good for cleanliness.
This 2-bedroom, 2-bathroom unit offers 1350 square feet of space and can comfortably accommodate up to 6 guests. Enjoy amenities like a private fenced yard, a swimming pool, a tennis court, and a fully equipped kitchen, perfect for a relaxing and enjoyable vacation.
Ocean/marina View - Pool - Free Kayaks Pickleball - Florida Keys, FL
9.7 111 reviews
Florida Keys, FL
06/20 – 06/27
$376/nighttotal: $2632 (7 )

Ocean/marina View - Pool - Free Kayaks Pickleball

2 5
apartment , Key Largo
This Key Largo yacht is located in the Kawama Yacht Club, a gated community at mile marker 100, just a half mile from Pilot House Marina. This accommodation has received excellent ratings for location, cleanliness, and user experience.
The yacht offers 1,300 square feet of space and can accommodate up to 6 guests with 2 bedrooms and 2 bathrooms. Amenities include a swimming pool, a terrace, a garden, parking, a kitchen with a fridge, freezer, microwave, and dishwasher, and two kayaks for exploring the surrounding waters.
Castaway 2/2 W/ 50` Ft. Dock On The Atlantic - Florida Keys, FL
9.7 90 reviews
Florida Keys, FL
06/20 – 06/27
$232/nighttotal: $1624 (7 )

Castaway 2/2 W/ 50` Ft. Dock On The Atlantic

2 2
apartment , Marathon
This Marathon Shores vacation rental is conveniently located just a 15-minute walk from Captain Hooks Marina and Dive Center, Sunset Park Beach, and Coco Plum Beach, making it easy to explore the area's natural beauty. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, two-bathroom home comfortably accommodates up to five guests. Amenities include a fully equipped kitchen, free Wi-Fi, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and barbecue grills, perfect for enjoying meals outdoors.
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