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Florida Keys, FL cottages
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381 Best cottages in Florida Keys, FL

Best family friendly Florida Keys, FL cottages

Among the 381 accommodations in Florida Keys, FL, here are the 4 best family friendly cottages

Wonderful Chalet, With Terrace & Private Patio  20 Miles From Key West. - Florida Keys, FL
10 44 reviews
Florida Keys, FL
09/08 – 09/10
$294/nighttotal: $588 (2 )

Wonderful Chalet, With Terrace & Private Patio 20 Miles From Key West.

1 2
cottage , Cudjoe Key
This smoke-free cottage is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and less than four miles from Florida Keys Beaches. This "Little Gem In Paradise" is rated excellent by guests and offers a peaceful garden setting perfect for relaxing.
This one-bedroom, one-bathroom cottage can accommodate up to four guests and features a private garden, terrace, and patio. Enjoy amenities like a fully equipped kitchen, washer/dryer, free WiFi, a swimming pool, a tennis court, and barbecue grills.
2br Island Cottage W/ Pool, Beach Access, Kitchen & Dock Fishing - Florida Keys, FL
Florida Keys, FL
09/08 – 09/10
$529/nighttotal: $1058 (2 )

2br Island Cottage W/ Pool, Beach Access, Kitchen & Dock Fishing

3 2
cottage , Big Pine Key
This beachside cottage in Summerland Key, Lower Florida Keys, is located a short distance from Looe Key Reef and Bahia Honda State Park.
This 625 sq. ft. pet-friendly cottage accommodates up to 6 guests and features a shared heated pool, complimentary kayaks, paddleboards, bikes, and on-the-go breakfast.
Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated! - Florida Keys, FL
9.8 55 reviews
Florida Keys, FL
08/04 – 08/07
$325/nighttotal: $975 (3 )

Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated!

1 4
cottage , Cudjoe Key
Palm Cottage, a pet-friendly Summerland Key vacation home, is located less than a mile from Florida Keys Beaches, Crab Key, and Pye Key, offering easy access to swimming, sunbathing, and exploring the natural beauty of the Keys.
This 480-square-foot cottage features two bedrooms, one bathroom, and accommodates four guests, providing a private patio, fully equipped kitchen, free Wi-Fi, and access to a shared pool and barbecue grills.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Florida Keys, FL
Florida Keys, FL
06/20 – 06/27
$616/nighttotal: $4312 (7 )

Cottage ∙ 1 Bedroom ∙ 4 Guests

1 2
cottage , Islamorada, Village of Islands
Little Bay Cottage is a secluded retreat on a lush one-acre tropical property in Islamorada, Village of Islands. It offers direct bay access, a protected dock for boats up to 34 feet, and stunning views of Florida Bay from the covered balcony.
The cottage has two bedrooms, two bathrooms, and a queen-size sleeper sofa, comfortably accommodating up to six guests. It features a modern kitchen with granite countertops and new appliances, as well as outdoor relaxation areas with hammocks, a pergola, and a tiki hut. Activities and attractions nearby include John Pennekamp Coral Reef State Park, Theater of the Sea, and Robbie's Marina.

Best Florida Keys, FL cottages with a garden

Large House W/ Free Sailboat, Kayaks, Snorkel And Fishing Gear - Florida Keys, FL
Florida Keys, FL
07/31 – 08/03
$494/nighttotal: $1482 (3 )

Large House W/ Free Sailboat, Kayaks, Snorkel And Fishing Gear

1 2
cottage , Key Largo
This Key Largo beach house is a short walk from Jimmy Johnson's Big Chill and Jacob's Aquatic Center, and within 3 miles of Bluefin Rock Harbor Marina and North Nest Key.
This one-bedroom, one-bathroom cottage offers 320 square feet of space, sleeps eight guests, includes a fully equipped kitchen with refrigerator and microwave, and features gas grills and a terrace.
Cozy, Perfect Conch Cottage! - Vo315 - Florida Keys, FL
9.2 33 reviews
Florida Keys, FL
06/19 – 06/23
$330/nighttotal: $1320 (4 )

Cozy, Perfect Conch Cottage! - Vo315

2 4
cottage , Cudjoe Key
Cozy, Perfect Conch Cottage, a Summerland Key vacation home, offers convenient access to Bahia Honda State Park and numerous Florida Keys water activities.
This 600-square-foot house features two bedrooms, one bathroom, and accommodates four guests, boasting a private pool, Jacuzzi, and fully equipped kitchen including a dishwasher.
Waterfront Cottage Near Key West, Sleeps 6 - Florida Keys, FL
9.4 29 reviews
Florida Keys, FL
11/25 – 11/27
$397/nighttotal: $794 (2 )

Waterfront Cottage Near Key West, Sleeps 6

2 6
cottage , Cudjoe Key
This charming 2-bedroom cottage is located in Summerland Key, just a short walk from Venture Out Keys and Venture Key, offering easy access to sailing and diving spots. The cottage has received excellent user ratings, making it a popular choice for travelers.
The 930-square-foot cottage comfortably accommodates up to 6 guests and features a well-equipped kitchen, a private outdoor space, and a shared pool and hot tub. You can enjoy amenities like air conditioning, free Wi-Fi, a TV, and a washer and dryer.
2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool - Florida Keys, FL
9.6 155 reviews
Florida Keys, FL
08/04 – 08/07
$427/nighttotal: $1281 (3 )

2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool

2 4
cottage , Islamorada, Village of Islands
This charming cottage is located at mile marker 76.7 in Islamorada, just a short drive from Caloosa Cove Marina and Robbie's Marina, offering a peaceful retreat away from the hustle and bustle of the main tourist areas. The cottage has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage has two bedrooms and comfortably accommodates four guests. Enjoy a refreshing dip in the heated swimming pool, shared exclusively with a select few cottages at Shady Palms, and take advantage of the starter pack with essential supplies, convenient parking, and family-friendly features.

Frequently Asked Questions about cottages in Florida Keys, FL

  • What are the top must-see attractions in the Florida Keys?

    The Florida Keys offer a plethora of attractions. For natural beauty, you can't miss Dry Tortugas National Park, with its historic fort and pristine coral reefs. Then there's Bahia Honda State Park, known for its gorgeous beach and old railroad bridge. For a taste of Key West, explore Duval Street, Mallory Square for the sunset celebration, and Ernest Hemingway's Home and Museum. Further up the Keys, John Pennekamp Coral Reef State Park provides incredible snorkeling and diving opportunities.
  • What are the best cottages in Florida Keys, FL?

  • How to spend a 5-day holiday in the Florida Keys?

    A five-day trip allows for a good exploration. Spend a day or two in Key West, enjoying the nightlife, history, and beaches. Allocate another day for exploring Dry Tortugas National Park, perhaps taking a boat tour. Consider a day trip to Islamorada, known as the Sport Fishing Capital of the World, for some water activities. Finally, spend a day relaxing on one of the many beautiful beaches in the Keys, like Bahia Honda State Park or Sombrero Beach.
  • What are the best cottages with a pool in Florida Keys, FL?

  • Are the Florida Keys a good destination to rent a cottage?

    Absolutely! The Florida Keys have many charming cottages available for rent, particularly in quieter areas like Islamorada or Marathon. These offer a more secluded and homey experience compared to hotels, perfect for a relaxing getaway. Look for rentals on websites specializing in vacation homes.
  • What are the best cottages with a jacuzzi in Florida Keys, FL?

  • What weather, wildlife, or natural hazards might affect travelers in the Florida Keys?

    The Keys have a subtropical climate, meaning hot and humid summers and mild winters. Hurricane season runs from June 1st to November 30th, so check forecasts before and during your trip. Wildlife includes various birds, sea turtles, and manatees. Be mindful of strong currents and potential encounters with marine life while swimming or snorkeling. Mosquitoes can be prevalent, especially in the evenings.
  • What are the best cottages for families and kids in Florida Keys, FL?

    The best cottages for families and kids in Florida Keys, FL are Secret Courtyard Cottage, 3br/3ba Sunset Cottage Located At The Villages Of Hawks Cay and Redlands Bungalow.

  • Are the Florida Keys pedestrian and cyclist-friendly?

    Key West, in particular, is quite pedestrian-friendly, especially in the downtown area. However, cycling is more challenging due to the traffic on some roads. Many areas have dedicated bike paths, and renting bikes is popular. In other parts of the Keys, car travel is often necessary due to distances between attractions.
  • What are the best pet friendly cottages in Florida Keys, FL?

  • Are there any unusual or hidden places to explore in the Florida Keys?

    Yes! The African Queen, a historic steamboat, is docked in Key Largo and offers tours. Furthermore, explore the backcountry roads for hidden beaches and nature trails. Consider visiting the less-visited state parks like Curry Hammock State Park for a more secluded experience.
  • What are the best cottages with parking in Florida Keys, FL?

  • What are some of the best cultural experiences that allow you to meet locals in the Florida Keys?

    Attending local events and festivals is a great way to interact with locals. Check local listings for smaller community events. Many restaurants and bars offer live music, creating opportunities for casual conversations. Visiting local art galleries and shops can also lead to interactions with artists and owners.
  • What are the best authentic dishes to taste in the Florida Keys?

    Fresh seafood is a must! Key lime pie is iconic, and you'll find many variations. Conch fritters are a popular appetizer, and stone crab claws are a seasonal delicacy. Many restaurants offer locally sourced ingredients, highlighting the Keys' culinary scene.
  • Are there any recommended items to pack for a stay in the Florida Keys?

    Pack light, breathable clothing for the warm weather. Sunscreen, sunglasses, and a hat are essential for sun protection. Bring swimwear, a reusable water bottle, and comfortable walking shoes. Insect repellent is also recommended, particularly for evening activities. If you plan on water activities, bring appropriate gear.

Nearby regions

Best Florida Keys, FL cottages with jacuzzi

Among the 381 accommodations in Florida Keys, FL, here are the 4 best cottages with a jacuzzi

Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Florida Keys, FL
9.6 14 reviews
Florida Keys, FL
08/04 – 08/07
$527/nighttotal: $1581 (3 )

Island Oasis ~ Your Paradise Awaits In Venture Out Resort!

2 4
cottage , Cudjoe Key
Island Oasis ~ Your Paradise Awaits in Venture Out Resort! is a waterfront cottage in Cudjoe Key, Florida, a short walk from Venture Out Keys, Venture Key, and Out Key, and 2.4 miles from Florida Keys Beaches.
This two-bedroom, two-bathroom vacation home sleeps six and features a fully equipped kitchen, private balcony, swimming pool, tennis court, and access to barbecue grills.
Imagine In The Keys - Venture Out Unit 073 - Florida Keys, FL
9.6 4 reviews
Florida Keys, FL
08/04 – 08/07
$508/nighttotal: $1524 (3 )

Imagine In The Keys - Venture Out Unit 073

2 4
cottage , Cudjoe Key
This Cudjoe Key waterfront cottage boasts stunning views and direct access to the water, located 2.4 miles from Florida Keys Beaches and within 6 miles of Upper Sugarloaf Key and Upper Sugarloaf Sound.
This 800-square-foot vacation home features two bedrooms, two bathrooms, a private patio, and accommodates up to six guests, offering a swimming pool, jacuzzi, and barbecue grills.
Fl Keys Cottage With Ocean Views - Venture Out Unit 395 - Florida Keys, FL
8.4 8 reviews
Florida Keys, FL
06/20 – 06/27
$351/nighttotal: $2457 (7 )

Fl Keys Cottage With Ocean Views - Venture Out Unit 395

2 1
cottage , Cudjoe Key
This Cudjoe Key cottage is located a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the natural beauty of the area. It is also just a few miles from Florida Keys Beaches, providing a peaceful and tranquil setting for your stay. This highly-rated cottage is perfect for a small family or group of friends seeking a relaxing getaway.
The cottage offers 650 square feet of space, with two bedrooms, one bathroom, and a capacity for six guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, as well as outdoor grilling and a prime seafront location.
Carpe' Diem Heart Of The Fl. Keys Specials - Florida Keys, FL
8.8 152 reviews
Florida Keys, FL
06/20 – 06/27
$204/nighttotal: $1428 (7 )

Carpe' Diem Heart Of The Fl. Keys Specials

3 2
cottage , Marathon
Carpe'Diem is a three-bedroom, two-bathroom apartment ideally located in Marathon, Florida Keys, at Mile Marker 50.3, offering direct access to the Great Atlantic for boating, fishing, and diving. This very good-rated apartment is only a few steps from the deck and dock, making it convenient for children and seniors.
The apartment features a fully equipped kitchen, three bedrooms, two full baths, a screened-in lanai, a 50-foot furnished dock with a six-person spa tub and gas grill, air conditioning, internet, parking, and a garden.

Best pet friendly Florida Keys, FL cottages

Among the 381 accommodations in Florida Keys, FL, here are the 4 best pet friendly cottages

**Turtle Cove Views @ Venture Out** 2br/2ba Cottage +35 Private Slip | 80 Pool - Florida Keys, FL
9.7 125 reviews
Florida Keys, FL
08/04 – 08/07
$634/nighttotal: $1902 (3 )

**Turtle Cove Views @ Venture Out** 2br/2ba Cottage +35 Private Slip | 80 Pool

2 4
cottage , Cudjoe Key
This charming cottage is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to fishing, snorkeling, and the beautiful Florida Keys scenery. The cottage consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 850-square-foot cottage comfortably sleeps up to 6 guests in its two bedrooms and two bathrooms. Enjoy a relaxing vacation with amenities like a private pool, spa, and tennis court, along with a fully equipped kitchen, barbecue grills, and a spacious terrace.
Charming Cottages, Dockage, Pool, Just Minutes To Key West - Florida Keys, FL
8.6 129 reviews
Florida Keys, FL
07/09 – 07/13
$380/nighttotal: $1520 (4 )

Charming Cottages, Dockage, Pool, Just Minutes To Key West

2 4
cottage , Cudjoe Key
This Summerland Key vacation home, located within three miles of Upper Sugarloaf Key and other nearby keys, offers easy access to various water activities in the Florida Keys.
This pet-friendly 790-square-foot house features two bedrooms, one bathroom, and accommodates four guests, complete with a swimming pool, kitchen appliances (refrigerator, microwave, oven, stovetop), a washer, and outdoor barbecue grills.
Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Florida Keys, FL
8.0 2 reviews
Florida Keys, FL
08/04 – 08/07
$794/nighttotal: $2382 (3 )

Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach

1 4
cottage , Islamorada, Village of Islands
This Islamorada beachfront cottage in Matecumbe offers direct ocean access, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under a mile from the Hurricane Monument and Florida Keys Brewing Co.
The 450-square-foot, one-bedroom, one-bathroom vacation home sleeps four and includes a private balcony, air conditioning, Wi-Fi, a swimming pool, parking, and concierge services.
Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking! - Florida Keys, FL
Florida Keys, FL
07/09 – 07/13
$920/nighttotal: $3680 (4 )

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking!

1 4
cottage , Islamorada, Village of Islands
This Islamorada pet-friendly cottage, located in the Matecumbe district, offers easy access to Bud n' Mary's Dive Center (a 14-minute walk) and Indian Key Historic State Park (a 6-minute walk).
This one-bedroom, one-bathroom vacation home sleeps four and features a private balcony, shared pool access, kayaks, bicycles, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Hurricane Monument and several state parks.
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