Cottages in Florida Keys at the best prices

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Florida Keys cottages
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277 Best cottages in Florida Keys

Best family friendly Florida Keys cottage rentals

Among the 277 accommodations in Florida Keys, here are the 4 best family friendly cottage rentals

Bayfront Cottage Located On The Bay In Sunset Cove With Sandy Beach - Florida Keys
9.8 24 reviews

Bayfront Cottage Located On The Bay In Sunset Cove With Sandy Beach

cottage, Key Largo
This Keys Conch Cottage in Key Largo offers a tropical waterfront setting on 0.4 hectares, providing direct access to a shared sandy beach and 30-metre dock, with Jimmy Johnson's Big Chill and Bluefin Rock Harbour Marina nearby. This family-friendly two-bedroom, two-bathroom holiday home accommodates up to six guests, featuring air conditioning, internet, a kitchen with a fridge, microwave, and dishwasher, plus complimentary kayaks and fishing equipment for enjoying the clear waters and local wildlife.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Florida Keys
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Islamorada, Village of Islands
Little Bay Cottage is located directly on Florida Bay in Islamorada, just off Overseas Highway at Mile Marker 82.2, within easy reach of attractions like John Pennekamp Coral Reef State Park and Robbie's Marina. The cottage is part of a gated compound offering privacy and security, and has a unique floor plan with a spacious living area, two bedrooms and two bathrooms, comfortably sleeping up to four guests.
The cottage features a modern kitchen with new appliances and granite countertops, as well as a full-size washer and dryer, central air conditioning, and WiFi. Guests can also enjoy a variety of outdoor spaces for relaxation, including a sunning area with lounge chairs, hammocks, a pergola and a tiki hut, as well as a protected dock for boats up to 10 metres long.
Cottage With Dock Space - Florida Keys
10 1 review

Cottage With Dock Space

cottage, Islamorada, Village of Islands
This Islamorada canal-side property, minutes from the Snake Creek Bridge and close to Theatre of the Sea, Founders Park, restaurants, and shops, offers a private dock, BBQ facilities, and a hammock for enjoying the waterfront.
The two-bedroom, one-bathroom house sleeps four guests and includes a kitchen with fridge, freezer, and microwave, air conditioning, a swimming pool, garden, parking, internet access, and pet-friendly accommodation.
Keys Waterfront Half-duplex, Ocean Side 37' Dock, - Florida Keys
10 120 reviews

Keys Waterfront Half-duplex, Ocean Side 37' Dock,

cottage, Marathon
This charming cottage in Marathon sits directly on a channel leading to open water, just three lots from the beach and less than four miles from Sombrero Beach. The property has received excellent user ratings and is perfect for a relaxing getaway.
The cottage is a comfortable 51 square metres and sleeps up to four guests. It has a fully equipped kitchen, air conditioning, a terrace, a garden, and parking for a boat trailer. The location offers easy access to water sports, nearby attractions, and restaurants.

Best Florida Keys cottages with a garden

Waterfront Key Colony Beach Home W/ Golf Cart! - Florida Keys
No reviews

Waterfront Key Colony Beach Home W/ Golf Cart!

cottage, Key Colony Beach
This Key Colony Beach holiday home is situated within 3.2km of Sunset Park Beach, the Marathon Visitor Centre, Curry Hammock State Park, San Pablo Catholic Church, and Captain Hooks Marina and Dive Centre.
The self-catering property features two bathrooms, a fully equipped kitchen, a private patio, and access to an outdoor pool and barbecue grills; free Wi-Fi is available in communal areas.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Florida Keys
8.4 63 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This waterfront cottage in Cudjoe Key is located within a short drive of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, making it ideal for exploring the area. It has been rated very good by previous guests.
The cottage has two bedrooms and one bathroom, accommodating up to four guests, and is 70 square metres in size. It features a fully equipped kitchen, laundry facilities, a swimming pool, a terrace, and a garden, as well as modern amenities and barbecue grills.
Canal Front, Dockage, 2 Bedroom,  2 Bath - Florida Keys
8.8 101 reviews

Canal Front, Dockage, 2 Bedroom, 2 Bath

cottage, Cudjoe Key
This charming waterfront cottage is situated on Cudjoe Key, just a short walk from Venture Key and a 6-mile drive from Upper Sugarloaf Key and Florida Keys Beaches, offering a peaceful escape in a beautiful location. It has been rated excellent by previous guests.
The cottage has two bedrooms and two bathrooms, making it suitable for a family or group of four. Guests can enjoy a range of amenities, including a private pool, barbecue grills, a fully equipped kitchen, and a washing machine, as well as a patio for relaxing and a TV for entertainment.
Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West! - Florida Keys
8.6 177 reviews

Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key oceanfront holiday home offers stunning views and easy beach access, located within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 47-square-metre self-catering property sleeps two, boasting a private garden, swimming pool, terrace, and amenities including a fully equipped kitchen, laundry facilities, and Wi-Fi.

Frequently Asked Questions about cottages in Florida Keys

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

    The Florida Keys offer a plethora of attractions. For natural beauty, you can't beat the Dry Tortugas National Park, accessible by boat or seaplane, with its historic fort and pristine coral reefs. Then there's Bahia Honda State Park, known for its stunning beaches and old railroad bridge. For a taste of Key West, visit Mallory Square for the sunset celebration, explore Duval Street's vibrant atmosphere, and see Ernest Hemingway's Home and Museum. Further up the Keys, John Pennekamp Coral Reef State Park offers incredible snorkeling and diving opportunities.
  • What are the best cottage rentals in Florida Keys?

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

    A five-day trip allows for a good exploration. Spend a day or two in Key West, soaking up the atmosphere, visiting the Hemingway House, and enjoying the sunset at Mallory Square. Allocate another day for exploring Dry Tortugas National Park. Consider a day trip to Islamorada, known as the "Sport Fishing Capital of the World," for some fishing or exploring the Theater of the Sea. The remaining day could be spent relaxing on the beaches of Bahia Honda State Park or exploring other areas that catch your interest, like Marathon or Key Largo.
  • What are the best cottage rentals with a pool in Florida Keys?

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

    Absolutely! The Florida Keys offer a wide variety of vacation rentals, including many charming cottages. You'll find them throughout the Keys, from Key Largo to Key West, offering a more intimate and homey experience than a hotel. Many are located near beaches or other attractions, providing easy access to activities and local life.
  • What are the best cottage rentals with a jacuzzi in Florida Keys?

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

    The Keys have a subtropical climate. Expect hot, humid weather, especially during summer. Hurricane season runs from June 1st to November 30th, so it's crucial to check forecasts before and during your trip. Wildlife encounters are common; be aware of mosquitoes, especially in the mangroves. Be mindful of strong currents and potential riptides when swimming. Also, be aware of the presence of venomous marine life, like certain types of fish and jellyfish.
  • What are the best cottage rentals for families and kids in Florida Keys?

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

  • Are the Florida Keys, United States pedestrian and cyclist-friendly?

    Key West, in particular, is quite pedestrian-friendly, especially in the downtown area. However, cycling can be challenging in some areas due to traffic and a lack of dedicated bike lanes on many roads. In other parts of the Keys, car travel is more common. Always prioritize safety and be aware of traffic conditions when walking or cycling.
  • What are the best pet friendly cottage rentals in Florida Keys?

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

    Yes! The African Queen, a historic boat featured in the movie of the same name, is a unique attraction in Key Largo. Further, explore the backcountry roads and find hidden beaches, or take a boat trip to explore secluded mangrove islands and discover hidden coves. Look for local guides who can take you to less-visited spots.
  • What are the best cottage rentals with parking in Florida Keys?

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

    Attending local events and festivals is a great way to meet people. Check local listings for smaller community gatherings. Many restaurants and bars offer a relaxed atmosphere where you can interact with locals. Consider taking a guided kayaking or snorkeling tour; the guides are often locals and can share insights into the area's culture and history.
  • What are the best authentic dishes to taste in the Florida Keys, United States?

    Fresh seafood is a must! Key West pink shrimp, stone crabs (in season), and conch fritters are local favorites. Many restaurants offer variations of Key lime pie, a classic dessert. Look for restaurants that source their ingredients locally; you'll find the freshest and most authentic dishes.
  • Are there any recommended items to pack for a stay in the Florida Keys, United States?

    Pack light, breathable clothing suitable for warm, humid weather. Don't forget swimwear, sunscreen (high SPF), a hat, sunglasses, and insect repellent. If you plan on watersports, bring appropriate gear. Comfortable walking shoes are essential, especially for exploring Key West. Consider bringing a reusable water bottle to stay hydrated.

Nearby regions

Best Florida Keys cottage rentals with jacuzzi

Among the 277 accommodations in Florida Keys, here are the 4 best cottage rentals with a jacuzzi

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

Breezy Point - Venture Out Unit 199

cottage, Cudjoe Key
Breezy Point cottage, a two-bedroom holiday home in Summerland Key, offers easy access to Bahia Honda State Park and other Florida Keys attractions, a short drive away.
This 70 square metre property features a combined kitchen-diner, sleeps six guests comfortably, and includes amenities such as air conditioning, Wi-Fi, a BBQ grill, and an 18ft driveway.
Imagine In The Keys - Venture Out Unit 073 - Florida Keys
9.6 4 reviews

Imagine In The Keys - Venture Out Unit 073

cottage, Cudjoe Key
This Cudjoe Key waterfront holiday home, situated 3.9km from Florida Keys Beaches and 9.7km from Upper Sugarloaf Key and Upper Sugarloaf Sound, offers stunning water views and direct water access.
The 74 square metre property boasts two bedrooms, two bathrooms, a private patio, swimming pool, jacuzzi, and barbecue facilities, sleeping up to six guests.
Water At Your Back Door - Florida Keys
8.8 34 reviews

Water At Your Back Door

cottage, Cudjoe Key
This waterfront cottage is situated on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to local attractions and a peaceful island setting. The cottage has received very good ratings from previous guests.
The property has two bedrooms and can accommodate up to six guests. Guests can enjoy a private pool, spa tub, barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Fl Keys Cottage With Ocean Views - Venture Out Unit 395 - Florida Keys
8.4 8 reviews

Fl Keys Cottage With Ocean Views - Venture Out Unit 395

cottage, Cudjoe Key
This charming cottage is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and a short drive from Florida Keys Beaches. It has received very good user ratings, making it a popular choice for travellers.
The cottage has two bedrooms and one bathroom, providing comfortable accommodation for up to six guests. Enjoy the peace and quiet of the seafront location, relax in the spa tub, and make use of the fully equipped kitchen, barbecue grills, and swimming pool.

Best pet friendly Florida Keys cottage rentals

Among the 277 accommodations in Florida Keys, here are the 4 best pet friendly cottage rentals

Tidewater Views At Venture Out - Florida Keys
9.8 264 reviews

Tidewater Views At Venture Out

apartment, Cudjoe Key
This charming cottage is situated on Cudjoe Key, a short 15-minute walk from Venture Key and Venture Out Keys, offering a peaceful retreat close to local attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage spans 79 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a private swimming pool, jacuzzi, and a fully equipped kitchen, making it ideal for both relaxation and entertaining.
Cottage ∙ 2 Bedrooms ∙ 6 Guests - Florida Keys
No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Cudjoe Key
This waterside holiday home in Cudjoe Key offers direct access to a sandy beach and is a short distance from local shops, restaurants, and the well-known Square Grouper establishment.
This cottage sleeps up to six guests and features two bedrooms and two bathrooms, alongside a heated swim spa, a private patio with a firepit, complimentary bicycles, a kayak, and boat dockage for vessels up to 25 feet.
Ocean Breeze House - Summer Fun Sleeps 8 Boating, Fishing And  Lobster Season. - Florida Keys
9.4 33 reviews

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

cottage, Cudjoe Key
This Summerland Key holiday home is less than 2km from Florida Keys Beaches, Crab Key, and Pye Key, and within 10km of Coupon Bight Aquatic Preserve and Venture Out Keys.
The 139 square metre property boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, swimming pool, on-site arcade, barbecue grills, and in-unit laundry facilities.
Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Florida Keys
8.0 2 reviews

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

cottage, Islamorada, Village of Islands
This beachfront cottage in Islamorada's Matecumbe district is situated less than 2.4km from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Company.
This 42 square metre self-catering property sleeps four, featuring a bedroom, bathroom, private balcony with potential ocean views, and amenities including air conditioning, Wi-Fi, a swimming pool, and parking.
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