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

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, 178 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!

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

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, 180 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 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, 490 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 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, 131 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.

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 Flagami

5.0 out of 5 average rating, 119 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.

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

4.9 out of 5 average rating, 420 reviews

Cottage By The Sea

Cottage By The Sea...! If you love turtles.This is the spot for you.I have a 150 pound giant sulcata tortoise in the front yard.And then I have four other little turtles that live in an enclosement , also in the front yard and a giant snapping turtle in my koi pond 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. It is walking distance to a famous local's Tiki Bar and Restaurant

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!

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, 185 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

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

4.96 out of 5 average rating, 151 reviews

2BR Island Cottage | Pool • Grill • Near Robbie’s

SEPTEMBER & OCTOBER SPECIAL — SAVE 30%! 🍋 Escape to Key Lime Cottage, a charming 2BR retreat in the heart of the Florida Keys. Enjoy a full kitchen, beautiful pool shared with just 6 neighboring cottages, outdoor seating, grill & fire pit, and paddle boards. Close to Robbie’s Marina and perfectly located for fishing, dining, exploring or simply relaxing. Limited fall dates remain at this special rate — book your Keys getaway while the deal lasts!

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 Coconut Grove

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.

Top guest favorite

Cottage in Coconut Grove

4.91 out of 5 average rating, 405 reviews

Coconut Grove Boutique Tropical Cottage w Parking

Experience boutique tropical living in the heart of Coconut Grove. This private stand-alone cottage is surrounded by lush gardens, yet just a short walk to CocoWalk, cafés, marinas & bayfront parks. Minutes to UM, Coral Gables, Brickell, MIA & the Port of Miami. Perfect for couples, solo travelers & business stays, with a full kitchen, washer/dryer, spacious deck & free gated parking. A peaceful Miami retreat with top-rated hospitality.