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Cottage holiday rentals in Florida Keys

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Top-rated cottage rentals in Florida Keys

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Guest favourite
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
4.97 out of 5 average rating, 112 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 favourite
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, 160 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Guest favourite
The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.
Cottage in Cudjoe Key
4.96 out of 5 average rating, 105 reviews

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Guest favourite
A serene pool area is framed by lush palm leaves, highlighting a sparkling pool with a bubbling spa. Sun loungers are arranged around the pool, complemented by a large blue umbrella providing shade.
Cottage in Islamorada
4.97 out of 5 average rating, 134 reviews

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Guest favourite
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
4.91 out of 5 average rating, 471 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 Park,40 mins to the Keys and 45mins to Miami and the beaches. Featuring 2 bdrms with superior quality mattress and TVs, with Netflix. New bathroom, washer/ dryer.The kitchen is equipped with a cook top,NO OVEN,microwave, dishwasher and a full size refrigerator. Outdoor security cameras. 600 SQ FT

Guest favourite
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, 174 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 favourite
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, 181 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!

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
4.89 out of 5 average rating, 177 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 favourite
Cottage in Goodland
4.98 out of 5 average rating, 141 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 favourite
Cottage in Marco Island
4.96 out of 5 average rating, 130 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

Top guest favourite
A cozy living area features a spacious sectional sofa arranged around a circular table. Large windows allow natural light to fill the space, opening to a view of the deck. A simple art piece hangs on the wall, adding a touch of color.
Cottage in Coconut Grove / Miami
4.9 out of 5 average rating, 393 reviews

Boutique Grove Cottage | Walk to Marina & Cafés

Experience natural luxury at this boutique cottage in the heart of Coconut Grove — a private tropical retreat surrounded by lush palms and vibrant gardens. Walk to the Marina, cafés, bayfront parks & CocoWalk. Perfect for couples or solo travelers, it offers a full kitchen, washer/dryer, free gated parking & a spacious deck with string lights. A top-rated, stand-alone escape near UM — your serene, central Miami hideaway for relaxation & connection.

Guest favourite
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
4.9 out of 5 average rating, 394 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 cottage rentals in Florida Keys

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Guest favourite
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
4.87 out of 5 average rating, 77 reviews

Turtle Cove Views at Venture Out

Guest favourite
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
4.96 out of 5 average rating, 23 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
4.89 out of 5 average rating, 45 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
3.8 out of 5 average rating, 5 reviews

Cozy, Perfect Conch Cottage! - VO315

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
4.8 out of 5 average rating, 107 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, 123 reviews

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

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
4.69 out of 5 average rating, 173 reviews

Calypso Cottage

Pet-friendly cottage rentals

Guest favourite
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, 95 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Guest favourite
An aerial view of the pool area reveals a large, rectangular swimming pool surrounded by lounge chairs and palm trees. The layout includes shaded cabanas, and the nearby landscape features a sandy area leading to the water's edge.
Cottage in Key Largo
4.91 out of 5 average rating, 94 reviews

Spacious cottage - the Calusa campground-keylargo

Top guest favourite
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, 161 reviews

Guest Cottage in tropical garden with big pool

Top guest favourite
A modern living space features a brown leather sofa adorned with patterned pillows. A wooden table with two stylish chairs is positioned against a light-colored wall. Large animal-themed artwork is displayed above the table, while a door leads to an outside area.
Cottage in Coral Gables
5 out of 5 average rating, 95 reviews

New Modern Near Airport - Cozy Very Clean

Top guest favourite
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
4.97 out of 5 average rating, 58 reviews

Waterfront Cottage Walk to World Famous Lorelei

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
4.79 out of 5 average rating, 14 reviews

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

Superhost
A charming bungalow exterior features a white wooden facade, surrounded by lush greenery and colorful flowers. Soft lighting lines the pathway and trellis, creating a welcoming ambiance. A small air conditioning unit is visible on the wall, enhancing comfort during warmer months.
Cottage in Miami
4.79 out of 5 average rating, 52 reviews

Enchanted Miami Cottage • Pet & Family Friendly!

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, 47 reviews

1 Bdrm Keys Cottage With Sleeping Loft Sleeps 7

Private cottage rentals

Guest favourite
A modern two-story home is surrounded by lush tropical vegetation. The exterior features a blend of white and blue walls, with large windows enhancing natural light. A pebble pathway leads towards the entrance, and the landscape is accented with various shrubs and palm trees.
Cottage in Miami
4.89 out of 5 average rating, 148 reviews

Coconut Grove - 1925 Historic Water Tower

Top guest favourite
A cozy bedroom features a queen size bed with luxurious bedding and a decorative pillow. A stylish lamp illuminates the space, while a ceiling fan offers airflow. Light-colored walls complement the patterned area rug, and a wooden wardrobe adds storage options.
Cottage in Miami
4.88 out of 5 average rating, 86 reviews

The Cottage

Guest favourite
A sailboat is moored near a wooden dock, surrounded by palm trees. The orange glow of sunset is visible in the background, reflecting on the calm water. The scene captures a tranquil moment along the bay.
Cottage in Marathon
4.96 out of 5 average rating, 28 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

Superhost
The living area features a vibrant blue sofa with decorative pillows, complemented by a soft gray armchair. A white coffee table sits in the center, surrounded by a gallery wall of beach-themed art. A circular dining table with light chairs is visible in the corner.
Cottage
4.8 out of 5 average rating, 61 reviews

Florida beach house with tropical garden

Guest favourite
The cottage is framed by lush tropical greenery, with a private brick path leading to a charming front deck. Large windows allow natural light to fill the inviting space, while palm trees and vibrant plants create a serene atmosphere in the surrounding garden.
Cottage in Miami
4.92 out of 5 average rating, 59 reviews

El chiringuito

Guest favourite
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

Keys Waterfront Oasis • Tiki • Private Pool • Dock

Top guest favourite
Cottage in Miami
4.96 out of 5 average rating, 55 reviews

Yellow Door CasaRita /Central Miami

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, 86 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

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