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Cottage holiday rentals in Monroe County

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Top-rated cottage rentals in Monroe County

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Top 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, 155 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
4.97 out of 5 average rating, 97 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 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
4.96 out of 5 average rating, 55 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

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!

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, 464 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
4.89 out of 5 average rating, 175 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
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, 129 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!

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, 388 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, 385 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

Guest favourite
A charming yellow cottage is framed by a white picket fence, with blue awnings above the windows and door. The entrance is marked by a simple white door. Lush greenery surrounds the property, enhancing the inviting appearance of the home.
Cottage in Key West
4.91 out of 5 average rating, 152 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.

Superhost
The cozy living area features a warm light from a lamp illuminating the space. A small wooden table and comfortable seating are provided, and a staircase leads to a loft. Large windows allow natural light to fill the space, with lush greenery visible outside.
Cottage in Key West
4.92 out of 5 average rating, 12 reviews

Romantic 1BD Cottage|Hemingway’s Hideaway Key West

💘 Valentine’s Special – 10% Off for February 2026! Escape to Hemingway’s Hideaway, a cozy 1BD cottage in Old Town Key West. Enjoy a loft, cathedral ceilings, and hardwood floors—perfect for couples or solo travelers. Relax by the pool or on private decks surrounded by lush greenery. Just minutes from Duval Street’s dining, art, and nightlife, this serene retreat blends island charm with modern comfort.

Guest favourite
A spacious outdoor tiki living area features a thatched-roof gazebo overlooking the ocean. Two kayaks rest on the dock, with a fishing rod and tackle box nearby. The scene captures a serene sunset, reflecting light across the water and creating a tranquil ambiance.
Cottage in Key Largo
4.97 out of 5 average rating, 125 reviews

Oceanfront Getaway | Kayaks, BBQ & Stunning View!

Imagine yourself "Paradise Living" at this completely remodeled modern Oceanfront Tiki Stay! Enjoy the beautiful Florida Keys in the relaxing community of Manatee Bay! This oceanfront tiny home feels just like your home away from home. Located right at the entrance of Monroe County, this hidden gem is just off Mile Marker 112 in Key Largo, FL. Booking relaxation is just a click away!

Popular amenities for cottage rentals in Monroe County

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

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, 76 reviews

Turtle Cove Views at Venture Out

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, 43 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

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, 104 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, 170 reviews

Calypso Cottage

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, 162 reviews

ATLANTIS...Ocean Front Cottage Retreat!

An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.
Cottage in Cudjoe Key
4.79 out of 5 average rating, 66 reviews

NAUTILUS...ocean front cottage retreat ~

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
4.92 out of 5 average rating, 91 reviews

Spacious cottage - the Calusa campground-keylargo

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, 93 reviews

New Modern Near Airport - Cozy Very Clean

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
4.77 out of 5 average rating, 13 reviews

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

Guest favourite
A light-filled living area features large glass doors that provide views of tropical landscaping. Comfortable seating includes a spacious sofa adorned with neutral pillows and two striped lounge chairs. A round coffee table sits on a patterned area rug, adding to the welcoming space.
Cottage in Miami
4.82 out of 5 average rating, 89 reviews

Coconut Grove Cottage

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
4.82 out of 5 average rating, 45 reviews

1 Bdrm Keys Cottage With Sleeping Loft Sleeps 7

A lush tropical garden is depicted, featuring vibrant yellow flowers amidst green foliage. Coral rock walls are visible in the background, along with a wooden gate that adds a rustic charm to the natural setting.
Private room in Miami
5 out of 5 average rating, 12 reviews

Beautifully Appointed Cottage in Coconut Grove

Guest favourite
A charming coastal rental is depicted, featuring blue and beige siding with large windows. The setting is by the water, offering a serene view. Outdoor seating options are visible nearby, along with palm trees and decorative plants enhancing the inviting exterior.
Cottage in Key Largo
4.81 out of 5 average rating, 27 reviews

Waterfront Keys Cottage w/ Sleeping Loft Sleeps 6

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, 145 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

Top 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

An aerial view showcases the sprawling property, with lush greenery surrounding the cottage and pool area. A vibrant sunset casts warm hues over the landscape, while the layout of the ranch and parking space is clearly visible. Tall trees accentuate the tranquil outdoor setting.
Cottage in Miami
4.62 out of 5 average rating, 26 reviews

Guest Apartment with Patio & Pool on 4 Acre Ranch

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, 162 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Guest favourite
An outdoor lounge area features comfortable seating arrangements with cushioned chairs and a sectional. A striped rug covers the deck, while a thatched roof provides shade. The adjacent waterway is visible, lined with boats and marina structures in the background.
Cottage in Key Largo
4.92 out of 5 average rating, 96 reviews

THE PARADISE

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

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