Compare best cottages in Florida Keys, FL from 100+ sites!

277 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Florida Keys, FL cottages
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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

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.
Wonderful Chalet, With Terrace & Private Patio  20 Miles From Key West. - Florida Keys, FL
10 45 reviews

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

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.
Cottage ∙ 2 Bedrooms ∙ 5 Guests - Florida Keys, FL
No reviews

Cottage ∙ 2 Bedrooms ∙ 5 Guests

cottage, Islamorada, Village of Islands
The Green Cottage is located in Turtle Cove, a private community of five vacation homes in Islamorada, Florida, offering pool and ocean views.
This 2-bedroom, 1-bathroom cottage accommodates up to 5 guests and features a queen bed in the master bedroom and a full/twin bunk bed in the second bedroom, with shared amenities including a pool, boat basin, kayaks, and paddleboards.

Best Florida Keys, FL cottages with a garden

Imagine In The Keys - Venture Out Unit 073 - Florida Keys, FL
9.6 4 reviews

Imagine In The Keys - Venture Out Unit 073

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.
Carpe' Diem Heart Of The Fl. Keys Specials - Florida Keys, FL
8.8 155 reviews

Carpe' Diem Heart Of The Fl. Keys Specials

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.
Cottage With Pool  And Boat Dockage Just Minutes To Key West! - Florida Keys, FL
8.6 168 reviews

Cottage With Pool And Boat Dockage Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key waterfront cottage offers stunning views and direct access to the water, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 390-square-foot vacation home features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, and a patio with barbecue grills.
Large House W/ Free Sailboat, Kayaks, Snorkel And Fishing Gear - Florida Keys, FL
No reviews

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

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.

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

Canal Front, Dockage, 2 Bedroom,  2 Bath - Florida Keys, FL
8.8 102 reviews

Canal Front, Dockage, 2 Bedroom, 2 Bath

cottage, Cudjoe Key
This waterfront cottage in Cudjoe Key is a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the area's natural beauty. It's also just a short drive from Upper Sugarloaf Key and Florida Keys Beaches, making it a perfect base for exploring the area. This vacation rental consistently receives excellent ratings from past guests.
The two-bedroom cottage can accommodate up to four guests and features a fully equipped kitchen, two bathrooms, a washing machine, a patio, and a television. Guests can enjoy the private outdoor pool, BBQ grills, and the tranquility of Cudjoe Key's serene environment.
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.
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.
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.

Best pet friendly Florida Keys, FL cottages

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

Flamingo Cottage Summer Fun. Pool, Boating, Fishing Lobster Season. - Florida Keys, FL
9.8 48 reviews

Flamingo Cottage Summer Fun. Pool, Boating, Fishing Lobster Season.

cottage, Cudjoe Key
The Flamingo Cottage is located in Summerland Key, just a short walk from Tonio's tiki bar and a 25-mile drive from Key West. This charming cottage boasts excellent ratings, making it a popular choice for travelers seeking a relaxing getaway. The cottage offers a private space with a full kitchen, accommodating up to four guests. Amenities include a shared outdoor pool, covered patio with a gas grill, and picnic area, providing opportunities for both relaxation and social gatherings.
Charming Cottages, Dockage, Pool, Just Minutes To Key West - Florida Keys, FL
8.6 130 reviews

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

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 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.
Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West! - Florida Keys, FL
8.6 178 reviews

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

cottage, Cudjoe Key
This Cudjoe Key oceanfront cottage, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning ocean views and easy beach access.
This 510-square-foot vacation home features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private patio, in-unit laundry, and access to a shared swimming pool and barbecue grills.
©2026 cozycozy.com