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Cottage vacation rentals in Florida Keys

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Top-rated cottage rentals in Florida Keys

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite

Cottage in Coconut Grove / Miami

4.9 out of 5 average rating, 379 reviews

Coconut Grove Private Garden Cottage + Parking

Escape to this charming private garden cottage in the heart of Coconut Grove in Miami’s most historic & lush neighborhood. Enjoy convenient, free gated parking, magical tropical greenery, & quiet, resort-style comfort just minutes from Biscayne Bay. Relax on the spacious deck or Tikki surrounded by nature & then retreat indoors to a fully furnished space with a well-equipped kitchen, washer/dryer, & cozy details. Walk to Downtown Grove parks, restaurants, cafés, shops, and bayfront attractions.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 129 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

A spacious living area features a vaulted pine ceiling and large windows providing views of the surrounding mangrove landscape. A comfortable gray sofa is positioned around a green coffee table, with a woven rug underfoot. A modern kitchen area and a tripod stand are visible in the background.

Cottage in Everglades City

4.98 out of 5 average rating, 158 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

Top guest favorite

A tiki-style outdoor seating area is shown, featuring comfortable wicker chairs and a coffee table positioned on a wooden deck. The space is surrounded by greenery and water, providing a relaxing atmosphere ideal for leisure or social gatherings.

Cottage in Key Largo

4.96 out of 5 average rating, 176 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

A well-maintained pathway leads to the entrance of a guest house, enclosed by wooden fencing and lush greenery. The clear blue sky complements the inviting outdoor space, while trees provide shade to the area.

Cottage in Homestead

4.92 out of 5 average rating, 445 reviews

Redlands Bungalow

Newly remodeled guest house with private entrance,yard with privacy fence,patio with gas grill and dining,detached from main house.10 mins walk to RF Orchids.15 mins drive to Everglades or Biscayne Ntl Parks,40 mins to the Keys and 45mins to Miami and the beaches. Featuring 2 bdrms with superior quality mattress and TVs, Netflix included. New bathroom, washer/ dryer.The kitchen is equipped with a cook top,NO OVEN,microwave, dishwasher and a full size refrigerator. Outdoor security cameras

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Top guest favorite

The kitchen features light cabinetry with modern stainless steel appliances, including a refrigerator and microwave. A spacious island offers seating for three on natural wood stools. Soft lighting enhances the countertops, and a subtle tile backsplash adds a clean, contemporary touch.

Cottage in Naples

4.9 out of 5 average rating, 246 reviews

Cottage Close to Vanderbilt Beach Heated Pool

2023 Complete Remodel West of 41 .Private Heated Saltwater Pool w/ 6’ Privacy Fenced backyard. 1 miles to Vanderbilt beach Cottage with screened Lanai, 50 inch HD tv, gas blackstone grill w/ceiling fans and wet bar with refrigerator for outdoor living. Great house for small families or couples. Both rooms have king beds, so ideal for 2 couples. A sofa sleeper has been added to sleep 6. Quartzite countertops with travertine Marble floors. Beach chairs, coolers, towels, and sand toys

The entrance features a charming porch with a wooden chair positioned beside large glass doors. Lush palm trees frame the cottage, while a bicycle rests against the wall. The pathway is lined with colorful pavers leading towards the water view beyond.

Cottage in Goodland

4.97 out of 5 average rating, 111 reviews

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Dockage, kayaks, and bikes available.

A small decorative sign is positioned on a tabletop, displaying the text 'Islamorada is My Happy Place' with a light, beach-themed design. Beside it, a carved figure of a bird shows intricate green and blue details, while a soft-glow lamp stands nearby, contributing to a cozy ambiance.

Cottage in Islamorada

4.96 out of 5 average rating, 113 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

A vibrant waterfront scene features a thatched-roof structure with several palm trees surrounding it. Jet skis are docked alongside a wooden pathway. Colorful umbrellas offer shade to seating areas, creating a welcoming atmosphere for visitors enjoying the sunny Florida weather.

Cottage in Key Largo

4.9 out of 5 average rating, 349 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

Top guest favorite

Cottage in Miami Lakes

4.98 out of 5 average rating, 222 reviews

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a kayak.

An outdoor dining area is presented, featuring a large table surrounded by six chairs. A gas grill is positioned nearby, and two lounge chairs are set alongside the table. A fenced yard provides a sense of privacy, complemented by a clear sky above.

Cottage in Fort Lauderdale

4.9 out of 5 average rating, 303 reviews

Centrally Located Private Cottage

2/2 Centrally located cottage in private neighborhood 1.5 miles from beach Las Olas and Wilton Drive. Features 6 person 54 jet hot tub common outside dining grill washer and dryer. Free onsite parking and fenced in yard! Come and enjoy great Florida weather and all of the attractions!

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Bungalows

Intimate homes. inviting architecture

Popular amenities for Florida Keys cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.

Cottage in Cudjoe Key

4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

Top guest favorite

The image captures a serene pool scene set against a vibrant sunset. A large lap pool is framed by comfortable loungers and shaded umbrellas, while a spacious daybed with a canopy rests nearby. Lush greenery envelops the area, creating a tranquil outdoor retreat.

Cottage in El Portal

4.94 out of 5 average rating, 139 reviews

Come chill at Miami Pool Cottage

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

Cottage in Cudjoe Key

4.8 out of 5 average rating, 5 reviews

Ocean Breeze at Venture Out 537

The cottage is surrounded by lush greenery, showcasing large glass windows that provide views of the lake. A balcony extends from the upper level, where seating is positioned for relaxation. The entrance leads to a deck area beside the water, enhancing the natural setting.

Cottage in Lazy Lake

4.88 out of 5 average rating, 65 reviews

Enchanting Hideaway - minutes from everything.

The exterior of a mid-rise home is shown, featuring a light-colored facade and a set of stairs leading to an elevated porch. The porch area is equipped with a table and umbrella, surrounded by tropical landscaping and a gravel driveway.

Cottage in Cudjoe Key

4.63 out of 5 average rating, 112 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

A spacious patio area features a private heated saltwater pool surrounded by tropical landscaping. Lounge chairs in blue are positioned around the pool, adjacent to a spa. A separate seating area is visible, offering a comfortable space for relaxation.

Cottage in Naples

4.88 out of 5 average rating, 95 reviews

Villa De Charme SaltWater Pool. Summer Available !

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

Cottage in Cudjoe Key

4.71 out of 5 average rating, 152 reviews

Calypso Cottage

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

4.9 out of 5 average rating, 154 reviews

ATLANTIS...Ocean Front Cottage Retreat!

Pet-friendly cottage rentals

The tranquil canal is illuminated by soft lights reflecting off the crystal-clear waters. Lush palm trees line the banks, and tiki huts with ambient lighting add to the serene atmosphere. The scene captures a peaceful nighttime setting with boats moored along the dock.

Cottage in Key Largo

4.96 out of 5 average rating, 81 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Top guest favorite

The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.

Cottage in Islamorada

4.95 out of 5 average rating, 41 reviews

Waterfront Cottage Walk to World Famous Lorelei

The living area showcases a comfortable faux leather sofa with decorative cushions. A coffee table sits on a striped rug, complementing the tiled floor. Adjacent to the sofa, a small dining table with stools is positioned near a window, allowing natural light to fill the space.

Cottage in Fort Lauderdale

4.93 out of 5 average rating, 175 reviews

Cozy house near downtown FLL - Patio/Parking/Pets*

A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.

Cottage in Naples

4.95 out of 5 average rating, 149 reviews

Tropical Cottage by the Sea- No Storm Damage

The cottage interior features a spacious sleeping area with a king-size bed dressed in a patterned cover. Light flows in through windows, complemented by a rattan chair and a small lamp. Bunk beds are visible in a semi-separate area, with artistic decor adding a whimsical touch.

Cottage in Key Largo

4.77 out of 5 average rating, 13 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

An open-concept living area features a modern kitchen with a spacious island and bar seating. Natural light filters through large windows, illuminating the stylish decor. A comfortable sofa is positioned near a round coffee table on a decorative rug, surrounded by artwork and plants.

Cottage in Naples

4.94 out of 5 average rating, 107 reviews

Cozy Beach House in North Naples

A spacious master bedroom features a king bed dressed in white linens accented by decorative pillows. Soft lighting from a bedside lamp complements the natural light filtering through sheer curtains. A cozy armchair and a wall-mounted TV enhance the comfortable atmosphere.

Cottage in Naples

4.82 out of 5 average rating, 105 reviews

Cozy Cottage Near Vanderbilt Beach

A charming green cottage is surrounded by lush trees. The front door, painted in a soft hue, is complemented by a large window above it. The path leading to the entrance is lined with stones, and nearby, tropical plants add to the inviting atmosphere.

Cottage in Fort Lauderdale

4.95 out of 5 average rating, 115 reviews

Charming 2 Bdrm Pool House near Hard Rock Casino

Private cottage rentals

Top guest favorite

A stone pathway leads through a garden area featuring tropical plants and vibrant flowers. A fenced gate opens to a private patio space, surrounded by wooden slats and lush greenery, providing a sense of seclusion and tranquility.

Cottage in Fort Lauderdale

5 out of 5 average rating, 61 reviews

Cozy Tropical Cottage. Your new Happy Place!

A spacious outdoor dining area features woven furniture under a bamboo canopy, surrounded by tall palm trees. Chic light fixtures hang from above, casting soft shadows. The waterfront offers a backdrop of skyline views, creating an inviting setting for guests to enjoy their meals.

Cottage in Miami

4.83 out of 5 average rating, 6 reviews

MIA Design District Cottage*Hottub*FreeParking

A seating area with bright blue chairs surrounds a white table, set against a backdrop of palm trees and a marina. Soft lighting is strung overhead, enhancing the outdoor space next to calm waters and a docked boat.

Cottage in Key Largo

4.92 out of 5 average rating, 79 reviews

Spacious cottage - the Calusa campground-keylargo

Top guest favorite

An outdoor seating area is presented with a shaded patio umbrella over a glass table. Comfortable gray wicker furniture is designed for relaxation, surrounded by neatly trimmed greenery and a decorative plant. A door is visible leading back into the cottage.

Cottage in Coral Gables

5 out of 5 average rating, 74 reviews

New Modern Near Airport - Cozy Very Clean

A sleek kitchen area features modern white cabinetry and stainless steel appliances, including a microwave and refrigerator. A light wood table with a circular glass top is positioned in the center, accompanied by a decorative plant on its surface. Natural light enters through a window with wooden blinds.

Cottage in North Miami

4.77 out of 5 average rating, 137 reviews

The Hidden Gem - Private Cottage in Biscayne Park

Cottage in Miami

4.82 out of 5 average rating, 87 reviews

Historic Cottage in the Heart of the Grove

An aerial view of a serene backyard features a swimming pool surrounded by tropical landscaping. A synthetic grass putting green is visible alongside a shaded area with an umbrella. The pool area is bordered by a patio and palm trees, creating a peaceful outdoor escape.

Cottage in Fort Lauderdale

4.94 out of 5 average rating, 17 reviews

Beautiful 2-1 Cottage w Pool in Fort Lauderdale

Top guest favorite

Cottage in Naples

5 out of 5 average rating, 82 reviews

Beach House on pond w/ HEATED pool - sleeps 6

Destinations to explore