Cottage vacation rentals in Monroe County

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Top-rated cottage rentals in Monroe County

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

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Guest favorite

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

4.95 out of 5 average rating, 105 reviews

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

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Top 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, 179 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.

LocationFamilyGetting around

Guest favorite

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

4.97 out of 5 average rating, 129 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.

FamilyLocationOutdoor spaces

Guest favorite

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, 177 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

ValueLocationPool

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

4.96 out of 5 average rating, 150 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.

FamilyLocationBackyard

Guest favorite

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, 489 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

LocationFamilyKitchen

Top guest favorite

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, 118 reviews

New Modern Near Airport - Cozy Very Clean

Enjoy a stylish experience at this centrally-located cottage 5 min from Miami Airport and 20 min from Port of Miami, Miami Beach, Key Biscayne, Coconut Grove, Brickell, Downtown Miami, minutes to Merrick Park Mall, Dadeland Mall, Dolphin Mall, & more. Our prime location puts you within easy reach of local attractions, dining, and entertainment options. Whether you're here for a romantic getaway or a solo adventure, our modern and clean 1-bedroom gem offers the perfect for an unforgettable stay.

FamilyLocationLong stay

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, 196 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!

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Top guest favorite

Cottage in Key Largo

5 out of 5 average rating, 110 reviews

My Little Paradise North Key Largo

Your slice of paradise in North Key Largo. New Cottage with all new appliances, bed, Sofa and TV's. This is a waterfront property located at Manatee Cove. By far the best place for Kayaking, Fishing and relaxing by the pool area or grill your catch of the day on the outdoor BBQ. Free internet, Tesla charging station is available and included with your rental. Kayak is included with your rental, life jackets must be worn while kayaking. NO BOATS OR JET SKIS ALLOWED ON THIS PROPERTY.

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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, 183 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!

ValueFamilyParks

Guest favorite

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

4.9 out of 5 average rating, 108 reviews

Spacious cottage - the Calusa campground-keylargo

Comfortable and spacious cottage in the center of KEY LARGO, close to all activities, Publix, bars and restaurants. ENJOY THE BEST SUNSETS OF THE FLORIDA KEYS IN THE HAMMOCK AREA. The facility park has a heated pool, basketball court, tennis court, boat ramp, marina and a children’s playground. Calusa is conveniently located next to John Pennekamp Park, Fishing Charters, Snorkeling, Scuba Diving and some of the best Seafood restaurants in town.

ValueFamilyDecor

Guest favorite

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

4.9 out of 5 average rating, 156 reviews

Coconut Grove - 1925 Historic Water Tower

The 1925 Water Tower is a cozy and welcoming home. This piece of Coconut Grove history has been completely remodeled to include all modern amenities. The home includes 1 loft Queen bedroom and a living, dining, kitchen and bath area on the first floor. Futon Queen sofa bed. Roku connected TV (no cable). Short walk to Coconut grove restaurants, marina and shops but car recommended to explore the city. Free Parking. Snacks and coffee/creamer.

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