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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

Lush tropical plants surround a cobblestone pathway leading to the cottage entrance. A tranquil waterfall feature is visible beside vibrant foliage, creating a serene garden atmosphere. Tall palm trees frame the scene, enhancing the sense of a peaceful outdoor retreat.

Cottage in Miami

5 out of 5 average rating, 101 reviews

Design District Tropical Garden Cottage

See Miami from the perspective of a local. We’re in Historic Buena Vista EAST. Lux older homes-tree lined streets, & a 2 block walk to the Design District’s A+shopping, art, restaurants. The cottage is a perfect home base to explore the best of Miami. 10-15 min to airport, beach, and Wynwood. 1 bedroom w king bed, extra daybed, lux shower. Guests rave about our location, the tropical garden, & zen-like waterfall. Free parking but suggest walking & Uber. PLEASE NOTE: children infant age only

Cottage in Cudjoe Key

4.93 out of 5 average rating, 131 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 is complemented by a wooden ceiling and large windows providing views of the water and surrounding greenery. Modern kitchen amenities are visible, along with a dining area furnished with stylish seating, creating a seamless indoor-outdoor experience.

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 wooden dock extends over tranquil waters, featuring two blue chairs positioned for scenic views. Sunlight reflects off the water's surface, while a clear blue sky and scattered clouds create a serene backdrop. The dock provides access to fishing and relaxation.

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!

A cozy front porch is adorned with wooden seating arrangements, featuring two chairs and a table. Light green shutters frame a window that provides views of the surrounding lush greenery. A small potted plant adds a touch of nature to the space.

Cottage in Fort Lauderdale

4.83 out of 5 average rating, 506 reviews

Historic Renovated Cottage w/ Private Heated Pool!

We invite you to be our guest in this beautiful, historic Key West style cottage. The Seminole River House at Sailboat Bend is located in Fort Lauderdale's historic Sailboat Bend neighborhood - close to everything! This 2 bedroom house features robes, Beekman 1801 bath products, Kuerig coffee maker, plush pool towels, heated pool and hot tub. The cottage is professionally cleaned between guests in accordance with stringent COVID-19 guidelines developed by Broward County.

Top guest favorite

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, 114 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, 354 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

Palm trees frame a sandy path leading to the beach. Gentle waves can be seen lapping at the shore under a partly cloudy sky. Lush grass grows on either side, adding a serene touch to the coastal scene.

Cottage in Key West

4.91 out of 5 average rating, 133 reviews

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Top guest favorite

Cottage in Miami Lakes

4.98 out of 5 average rating, 226 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.

Vacation rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes. inviting architecture

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Florida Keys cottage rentals

Free parking on premises

Air conditioning

Beachfront 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

4.93 out of 5 average rating, 82 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

An aerial view showcases the tranquil neighborhood, with palm trees lining the streets. The clear blue ocean stretches into the horizon, contrasting with the white rooftops of nearby homes and the vibrant greenery of the surroundings.

Cottage in Hollywood

4.93 out of 5 average rating, 167 reviews

Cozy beach cottage steps away from Hollywood Beach

A paved pathway is lined with palm trees and potted plants, leading towards the beach in the background. The scene captures the essence of the community with neighboring cottages visible on either side and a clear blue sky overhead.

Cottage in Pompano Beach

4.91 out of 5 average rating, 109 reviews

Pompano Beach Private Ocean Cottage Unit 11.

An outdoor dining area features a large wooden table surrounded by high-backed chairs, beneath a thatched roof supported by intricately carved wooden pillars. Soft lighting from chandeliers illuminates the space, with a view of palm trees and a calm water backdrop.

Cottage in Key Largo

4.33 out of 5 average rating, 6 reviews

Tropical House By The Shore at Largo Resort

The charming cottage is framed by vibrant tropical landscaping, featuring lush palm trees and colorful plants. A sandy pathway leads to the covered porch with multiple glass doors, inviting natural light into the cozy entrance.

Cottage in Islamorada

Cottage on Bayfront Estate – Pool, Beach, & Dock

Tall palm trees are seen standing along the beach, framing a lifeguard tower. The ocean reflects soft light under a cloudy sky, creating a serene atmosphere. Figures in the distance suggest a quiet beach setting, enhancing the sense of calm.

Cottage in Hollywood

4.98 out of 5 average rating, 42 reviews

Beautiful 3 bedroom cottage with private rooftop

A fenced backyard features a sparkling pool surrounded by lush greenery. Several lounge chairs are positioned near the pool, inviting relaxation under the shade of palm trees. A patio umbrella offers additional shade for outdoor enjoyment.

Cottage in Pompano Beach

4.68 out of 5 average rating, 57 reviews

Beautiful tropical villa with pool-close to beach

A welcoming bedroom features a spacious bed adorned with tropical-themed linens and decorative pillows. Natural light fills the room through a doorway leading to an outdoor area. Colorful beach towels are neatly arranged at the foot of the bed, and nautical decor enhances the ambiance.

Cottage in Key Largo

4.77 out of 5 average rating, 30 reviews

Cottage w/ Bay View FREE Kayaks, Snorkel & More

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, 62 reviews

Cozy Tropical Cottage. Your new Happy Place!

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

4.78 out of 5 average rating, 139 reviews

The Hidden Gem - Private Cottage in Biscayne Park

Cottage in Naples

4.9 out of 5 average rating, 29 reviews

Cheerful 3 bedroom Cottage near the beach!

The exterior of a Florida-style cottage is showcased in the evening light, surrounded by lush tropical plants. Soft lighting illuminates the pathway leading to the entrance, while a small seating area with a table is visible on the patio, inviting relaxation in the outdoor space.

Cottage in North Miami

4.79 out of 5 average rating, 47 reviews

Florida beach house with tropical garden

An open living space features high wooden beams and a blue area rug. A small dining area is seen with two white chairs beside a light wood table. Nearby, a kitchenette is visible, alongside a staircase leading to an upper sleeping area.

Cottage in Islamorada

4.79 out of 5 average rating, 156 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

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

A cozy outdoor fire pit is surrounded by lush greenery and several comfortable chairs. Vibrant plants create a private atmosphere, while soft lighting enhances the serenity of the space. The warm glow of the fire adds a welcoming touch against the backdrop of a nighttime sky.

Cottage in Naples

4.97 out of 5 average rating, 31 reviews

Cozy Cove

Cottage in Key Largo

4.85 out of 5 average rating, 47 reviews

Welcome to the Islands- Pool-Marina-Kayak

Cottage rentals with a hot tub

A modern living space features a cozy gray sofa and a round dining table with two chairs. A sleek kitchenette with stainless steel appliances is visible. A large wall-mounted TV displays a beach scene, while soft lighting illuminates the neutral-colored walls and plush area rug.

Cottage in Miami

4.89 out of 5 average rating, 9 reviews

MIA Design District Cottage*Hottub*FreeParking

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, 142 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

4.83 out of 5 average rating, 6 reviews

Ocean Breeze at Venture Out 537

An outdoor seating area features a round table surrounded by iron chairs, overlooking tranquil waters. Lounge chairs are positioned along the railing. The covered porch provides shade, with lush greenery visible across the waterway, enhancing the serene setting.

Cottage in Cudjoe Key

4.86 out of 5 average rating, 37 reviews

Tidewater Views at Venture Out

The exterior of the Conch Cottage features a light green facade with large windows allowing natural light. Palm trees frame the entrance, and a clear driveway leads to the door marked with the number 315. A window air conditioning unit is also visible.

Cottage in Cudjoe Key

Cozy, Perfect Conch Cottage! - VO315

A comfortable living area features a dark gray sofa adorned with various throw pillows, complemented by a circular dining table. The modern kitchen showcases stainless steel appliances and granite countertops, with bar stools positioned at the counter. Colorful artwork enhances the walls, contributing to a cheerful ambiance.

Cottage in Fort Lauderdale

4.9 out of 5 average rating, 309 reviews

Centrally Located Private Cottage

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, 113 reviews

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

Destinations to explore