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Cottage vacation rentals in Florida Keys

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Top-rated cottage rentals in Florida Keys

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Top guest favorite
Lush tropical plants surround a winding brick pathway leading to the cottage entrance. Ferns, colorful foliage, and ornamental features create a serene garden environment. The entrance is framed by trees and offers glimpses of the cottage's sliding glass doors.
Cottage in Miami
5 out of 5 average rating, 102 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

Guest favorite
A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.
Cottage in Cudjoe Key
4.94 out of 5 average rating, 147 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.

Guest favorite
A wooden dock juts out over calm water, flanked by mangrove vegetation. Two adirondack chairs are positioned for relaxation, offering unobstructed views of the water. A cozy cottage is visible in the background, surrounded by palm trees, under a clear blue sky.
Cottage in Everglades City
4.98 out of 5 average rating, 167 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 serene view of a canal features lush palm trees lining wooden docks. A white boat is moored nearby, while a clear blue sky with scattered clouds reflects the peaceful surroundings.
Cottage in Key Largo
4.96 out of 5 average rating, 180 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!

Top guest favorite
A bright living area features large glass sliding doors that open to a private patio with views of lush greenery. A round dining table with four chairs is positioned adjacent to the doors, while a dark sofa is placed nearby, creating a welcoming and open atmosphere.
Cottage in Naples
4.98 out of 5 average rating, 182 reviews

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

Superhost
The living area features a light blue sofa and a dark blue armchair, complemented by a small table with a potted plant. A spacious kitchen with wooden cabinetry and modern appliances is visible, along with four bar stools by the counter. Natural light enters through a nearby window.
Cottage in Homestead
4.92 out of 5 average rating, 457 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

Superhost
A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.
Cottage in Little Torch Key
4.88 out of 5 average rating, 173 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!

Guest favorite
An exterior view of the suite features a bright yellow wall with a vibrant blue door. Two white chairs and a small blue table are positioned in front, with a potted orchid placed centrally on the table. A window is visible beside the entrance.
Cottage in Fort Lauderdale
4.94 out of 5 average rating, 570 reviews

Paradise Suite

Enjoy a stay in a peaceful and quiet suite with a private and relaxing back yard. Also benefit from a private entrance. Microwave, fridge, toaster, coffee maker are available for your convenience. In short, four words to describe my place: Clean, Cozy, Quiet, and Very Private. We are 3.5 miles from Las Olas Blvd, 5.8 miles from the beach, 4.7 miles from FLL Airport, 5.3 miles from Hard Rock Casino, less than a mile from the interstate I-95, and about 5 miles from Port Everglades.

Top guest favorite
Cottage in Goodland
4.98 out of 5 average rating, 129 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. Boat Parking, Dockage, kayaks, and bikes available.

Guest favorite
A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.
Cottage in Islamorada
4.97 out of 5 average rating, 125 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!

Guest favorite
Cottage in Marco Island
4.97 out of 5 average rating, 118 reviews

Coastal Paradise! Kayaks+Bikes+Fishing+Boat Dock

Direct back bay access+ boat dock & lift+ kayaks + bikes. 1 mile to Everglades National Park! Minutes to shops & dining! Adorable spacious home- perfect for a seaside retreat!. Designed for dockside enjoyment: hammocks, swing chairs, outdoor dining - 5 minute boat ride to beach -12 minute car ride to beach -Walk to waterfront dining & live music -Kayak in the Everglades -Fish off the dock -Cool, rustic Old Florida vibe -Bring your boat or rent one

Guest favorite
A window reveals a lush garden filled with tropical plants and flowers. The words 'Keys Life' are displayed on a wooden sign above the window, enhancing the connection to the surrounding nature.
Cottage in Key Largo
4.89 out of 5 average rating, 376 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

Popular amenities for Florida Keys cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Beachfront cottage rentals

Guest favorite
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
4.94 out of 5 average rating, 94 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Superhost
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
4.91 out of 5 average rating, 182 reviews

Cozy beach cottage steps away from Hollywood Beach

A charming blue exterior of the rental is complemented by a wooden deck, creating an inviting entrance. Lush palm trees and surrounding greenery enhance the outdoor space, while large windows provide ample natural light to the interior.
Cottage in Key Largo
4.79 out of 5 average rating, 28 reviews

Keys Cottage with Sleeping Loft| Sleeps 6

A guest room features a queen-sized bed adorned with a floral comforter. Two wooden nightstands with lamps flank the bed. French doors open to the outdoor garden, while light-colored curtains soften the sunlight filtering in from the windows.
Private room in Key Largo
4.58 out of 5 average rating, 745 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

Guest favorite
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, 46 reviews

Beautiful 3 bedroom cottage with private rooftop

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
4.68 out of 5 average rating, 165 reviews

Calypso Cottage

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, 31 reviews

Cottage w/ Bay View FREE Kayaks, Snorkel & More

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
4.89 out of 5 average rating, 161 reviews

ATLANTIS...Ocean Front Cottage Retreat!

Private cottage rentals

Superhost
A spacious bedroom is furnished with a large, intricately designed bed framed in light wood, complemented by crisp white bedding. The room features a large window allowing natural light to fill the space, along with light-colored wood flooring and a minimalist side table.
Cottage in Key Largo

Beach Cottage

Top guest favorite
The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.
Cottage in Key Colony Beach
5 out of 5 average rating, 12 reviews

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

Guest favorite
A spacious outdoor area is surrounded by lush greenery and features a paved patio. Comfortable seating is arranged on the patio, inviting relaxation. A charming cottage with a red-tiled roof stands in the background, under a clear blue sky.
Cottage in Fort Lauderdale
4.89 out of 5 average rating, 55 reviews

Cozy 1 Bedroom Cottage in Fort Lauderdale!!!!

A cozy living area features a brown leather sofa and a low wooden coffee table, set against a backdrop of wooden paneling. Large glass doors reveal a scenic view outside. A television is mounted on the wall, and decorative items are arranged on a nearby shelf.
Cottage in Islamorada
4.78 out of 5 average rating, 160 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Top guest favorite
A charming cottage exterior is highlighted by a vibrant floral mural along the white walls. A bright yellow door welcomes guests, framed by a small awning. A stone pathway leads to the entrance, complemented by an inviting outdoor seating area on green turf.
Cottage in Miami
4.96 out of 5 average rating, 46 reviews

Calming CasaRita Cottage near(Shops,Cruise,Air)

A living area features a comfortable blue sofa paired with a matching armchair. A coffee table sits atop a decorative area rug. A modern television is positioned on a white entertainment unit. Natural light enters through a window with light-colored coverings, enhancing the spacious feel.
Cottage in Islamorada
4.79 out of 5 average rating, 84 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

Guest favorite
An aerial view of a scenic bay area showcases waterfront homes alongside lush palm trees. Calm waters reflect the clouds above, while winding canals create a picturesque layout for the neighborhood. The horizon features a soft gradient of colors as the sun sets.
Cottage in Naples
4.88 out of 5 average rating, 8 reviews

Beautiful house on the bay!

A charming green cottage is surrounded by a landscaped area featuring palm trees. A wooden deck leads to the front entrance, and bright blue chairs are positioned on the gravel patio. A neighboring structure is partially visible in the background.
Cottage in Marathon
4.83 out of 5 average rating, 41 reviews

1 Bdrm Keys Cottage With Sleeping Loft |Sleeps 8

Cottage rentals with a hot tub

Guest favorite
A modern living area features a gray sofa with a white throw blanket, positioned on a plush rug. A flat-screen TV showcases a serene ocean view. The kitchen area includes sleek white cabinetry, stainless steel appliances, and a small dining table with bar stools, creating a functional and inviting space.
Cottage in Miami
4.92 out of 5 average rating, 13 reviews

Cottage@MIA Design District |Hot tub|FreeParking

Superhost
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
4.86 out of 5 average rating, 72 reviews

Turtle Cove Views at Venture Out

Guest favorite
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
4.95 out of 5 average rating, 19 reviews

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

Superhost
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
4.88 out of 5 average rating, 41 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
4.33 out of 5 average rating, 3 reviews

Cozy, Perfect Conch Cottage! - VO315

Cottage in Fort Lauderdale
New place to stay

Comfy Coastal Cottage with Hot Tub

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
Cottage in Cudjoe Key
4.82 out of 5 average rating, 103 reviews

OCEANIA... water front cottage retreat ~

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, 120 reviews

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

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