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Florida Keys, FL cottages
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277 Best cottages in Florida Keys, FL

Best family friendly Florida Keys, FL cottages

Among the 277 accommodations in Florida Keys, FL, here are the 4 best family friendly cottages

Waterfront Cottage Near Key West, Sleeps 6 - Florida Keys, FL
9.4 29 reviews

Waterfront Cottage Near Key West, Sleeps 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.
Palm Cottage - Sleeps 4  Summer Fun ..Lobster Season. - Florida Keys, FL
9.8 55 reviews

Palm Cottage - Sleeps 4 Summer Fun ..Lobster Season.

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
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

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.
Water At Your Back Door - Florida Keys, FL
8.8 34 reviews

Water At Your Back Door

cottage, Cudjoe Key
This waterfront vacation rental is conveniently located near Venture Key, Venture Out Keys, and Out Key, and is within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches. It has received very good ratings from previous guests. The two-bedroom cottage can comfortably accommodate up to six guests. The home features a private pool, a hot tub, a tennis court, and a barbecue grill for your enjoyment.

Best Florida Keys, FL cottages with a garden

Breezy Point - Venture Out Unit 199 - Florida Keys, FL
No reviews

Breezy Point - Venture Out Unit 199

cottage, Cudjoe Key
This Summerland Key cottage, a short drive from Cudjoe Key, boasts an oceanfront location near the beaches of the Keys archipelago and Upper Sugarloaf Key.
The 750-square-foot vacation home features two bedrooms, one bathroom, and accommodates up to six guests, offering a private patio with a barbecue, a shared pool and hot tub, and in-unit laundry.
Mile Marker Mahi - Venture Out #465 - Florida Keys, FL
9.6 55 reviews

Mile Marker Mahi - Venture Out #465

cottage, Cudjoe Key
This Cudjoe Key cottage is a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the island's attractions. With an excellent user rating, it's a popular choice for travelers seeking a relaxing and comfortable stay.
The two-bedroom, two-bathroom home comfortably accommodates four guests and features a fully equipped kitchen, a private patio, and a spa tub. Guests can enjoy the beautiful ocean views, relax in the spa tub, and grill fresh seafood on the barbecue.
Quaint Cottage, Pool, Dockage Just Minutes To Key West! - Florida Keys, FL
9.2 328 reviews

Quaint Cottage, Pool, Dockage Just Minutes To Key West!

cottage, Cudjoe Key
This oceanfront Cudjoe Key cottage boasts stunning views and easy beach access, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
This 790-square-foot vacation home features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private balcony, swimming pool, and on-site barbecue grills.
101 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Florida Keys, FL
10 2 reviews

101 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Cudjoe Key
This cottage in Cudjoe Key offers direct access to Cudjoe Bay and the ocean with a private launch and dock, providing spectacular sunset views and wildlife viewing opportunities, located approximately 20-23 miles from Key West.
This 1090 square foot, owner-operated vacation home features 2 bedrooms and 2 bathrooms to sleep 4 guests, a fully equipped kitchen with a grill, air conditioning, and is conveniently close to Key West attractions, Looe Key Reef, Bahia Honda State Park, and the Dolphin Research Center.

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

Beautiful Cottage & Amenities In Gated Community - Florida Keys, FL
10 2 reviews

Beautiful Cottage & Amenities In Gated Community

cottage, Cudjoe Key
This Cudjoe Key vacation home is conveniently located in Summerland Key, a short 10-minute walk from Venture Out Keys, Venture Key, and Out Key, and a 2.4-mile drive to Florida Keys Beaches.
The two-bedroom, two-bathroom cottage sleeps five, features a fully equipped kitchen, private pool, jacuzzi, tennis court, BBQ grills, game room, and free Wi-Fi.
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 Cudjoe Key cottage is located just a short drive from Bahia Honda State Park and Coupon Bight Aquatic Preserve, offering easy access to the beautiful waters of the Florida Keys. Guests consistently rate this rental as excellent, making it a popular choice for travelers seeking a comfortable and convenient stay.
This two-bedroom, one-bathroom cottage comfortably accommodates up to four guests and features a spacious 800-square-foot floor plan. Enjoy amenities such as a private backyard courtyard, a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, and a large patio perfect for relaxing and enjoying the Florida sunshine.
Fl Keys Cottage With Ocean Views - Venture Out Unit 395 - Florida Keys, FL
8.4 8 reviews

Fl Keys Cottage With Ocean Views - Venture Out Unit 395

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.
Canal Front With Open Water Views In Venture Out - Lot 529 - Florida Keys, FL
10 3 reviews

Canal Front With Open Water Views In Venture Out - Lot 529

cottage, Cudjoe Key
This Summerland Key waterfront cottage boasts stunning views and is a short drive from Florida Keys beaches (13 minutes), Upper Sugarloaf Key (8 minutes), and Bahia Honda State Park.
The two-bedroom, two-bathroom vacation home sleeps six and features a heated pool, hot tub, full kitchen with appliances including a lobster pot and ice maker, in-unit laundry, free Wi-Fi, and a smart TV.

Best pet friendly Florida Keys, FL cottages

Among the 277 accommodations in Florida Keys, FL, here are the 4 best pet friendly cottages

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking! - Florida Keys, FL
No reviews

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

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.
Tidewater Views At Venture Out - Florida Keys, FL
9.8 264 reviews

Tidewater Views At Venture Out

apartment, Cudjoe Key
This Cudjoe Key cottage is a short 15-minute walk from Venture Key and Venture Out Keys, offering a peaceful escape near the beautiful Florida Keys. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
The 850-square-foot cottage comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. Enjoy the convenience of a fully equipped kitchen, a private patio, a spa tub, a swimming pool, and a barbecue grill for relaxing evenings.
Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Florida Keys, FL
8.0 2 reviews

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

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.
Ocean Breeze House - Summer Fun Sleeps 8 Boating, Fishing And  Lobster Season. - Florida Keys, FL
9.4 33 reviews

Ocean Breeze House - Summer Fun Sleeps 8 Boating, Fishing And Lobster Season.

cottage, Cudjoe Key
This Summerland Key vacation home is less than 1.2 miles from Florida Keys beaches, Crab Key, and Pye Key, offering easy access to water activities and located within 6 miles of Coupon Bight Aquatic Preserve and Venture Out Keys.
This 1500-square-foot rental boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, terrace, free Wi-Fi, a fully equipped kitchen, in-unit laundry, and an on-site arcade.
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