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Cottage vacation rentals in Monroe County

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Top-rated cottage rentals in Monroe County

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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

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!

4.89 out of 5 average rating, 178 reviews
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

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

4.95 out of 5 average rating, 105 reviews
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

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

4.91 out of 5 average rating, 491 reviews
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

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.

4.95 out of 5 average rating, 182 reviews
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

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.

4.97 out of 5 average rating, 131 reviews
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

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

4.9 out of 5 average rating, 421 reviews
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

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.

5.0 out of 5 average rating, 120 reviews
Top guest favorite
A shared heated pool is surrounded by lush tropical landscaping, providing a serene atmosphere. A shaded pavilion equipped with seating and dining options is nearby, offering a spot for relaxation. The pool area features a concrete deck and two lounge chairs for sunbathing.
Cottage in South Miami

Cottage-Private Gated Estate w/heated Pool Near UM

A peaceful & secure place. Perfect for a peaceful getaway, artist/writer sabbatical. Recharge in the quiet oasis. Renovated, freestanding 726 SF cottage on 1.5 acre private gated estate w/ lush gardens. Close to UM, & Coral Gables. Quiet neighborhood, yet close to everything you need. 20-min walk/5-min car ride to UM. Self-check-in w/keypad entry. Separate bedroom w/ king-size bed, kitchen, washer/dryer, tv, high-speed fiber optic wi-fi, huge heated pool (shared) with outdoor shower. Pet Fee.

4.94 out of 5 average rating, 101 reviews
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

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!

4.96 out of 5 average rating, 196 reviews
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

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!

4.89 out of 5 average rating, 185 reviews
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

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!

4.96 out of 5 average rating, 152 reviews
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

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.

4.9 out of 5 average rating, 156 reviews

Popular amenities for Monroe County cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Guest favorite
A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.
Cottage in Cudjoe Key

2Bd/1Ba Waterfront Retreat w/35’ Dock

4.81 out of 5 average rating, 37 reviews
Superhost
Cottage in Cudjoe Key

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

4.84 out of 5 average rating, 45 reviews
Superhost
A charming cottage is positioned along a serene waterfront, featuring a covered porch with seating. Two kayaks are stored upright next to the seawall. Sun loungers are arranged neatly along the edge of the water, with palm trees providing a tropical backdrop.
Cottage in Cudjoe Key

Tidewater Views at Venture Out

4.89 out of 5 average rating, 47 reviews
Guest favorite
Cottage in Cudjoe Key

FL Keys Retreat - Community pool and hot tub

5.0 out of 5 average rating, 10 reviews
Guest favorite
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

Calypso Cottage

4.74 out of 5 average rating, 191 reviews
Cottage in Cudjoe Key

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

4.66 out of 5 average rating, 131 reviews
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

Cozy, Perfect Conch Cottage! - VO315

4.0 out of 5 average rating, 7 reviews
Superhost
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

OCEANIA... water front cottage retreat ~

4.79 out of 5 average rating, 121 reviews

Pet-friendly 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

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

4.93 out of 5 average rating, 104 reviews
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

Spacious cottage - the Calusa campground-keylargo

4.9 out of 5 average rating, 108 reviews
Top guest favorite
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

Waterfront Cottage Walk to World Famous Lorelei

4.97 out of 5 average rating, 71 reviews
Superhost
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

1 Bdrm Keys Cottage With Sleeping Loft Sleeps 7

4.75 out of 5 average rating, 63 reviews
Guest favorite
A spacious sleeping area features a Queen bed dressed in crisp white linens and a textured throw blanket. The walls are adorned with a colorful geometric pattern, and large windows are dressed with dark curtains. A kitchenette is visible in the background, highlighting practical amenities.
Cottage in Little Havana

6 yr SuperHost! Guesthouse free parking & laundry

4.86 out of 5 average rating, 74 reviews
Superhost
An entryway framed by a stone arch leads to a cottage surrounded by lush tropical foliage. Soft outdoor lighting highlights the pathway, while an inviting wooden door stands open, revealing a glimpse of a cozy interior with warm tones.
Cottage in Coral Gables

Coral Rock Village Cottage #4

4.86 out of 5 average rating, 22 reviews
Superhost
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

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

4.82 out of 5 average rating, 17 reviews
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

Keys Waterfront Oasis • Tiki • Private Pool • Dock

5.0 out of 5 average rating, 15 reviews

Private cottage rentals

Top guest favorite
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

THE PARADISE

4.93 out of 5 average rating, 118 reviews
Top guest favorite
Cottage in Key Largo

My Little Paradise North Key Largo

5.0 out of 5 average rating, 111 reviews
Guest favorite
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

Waterfront cottage w/ MotherInLaw suite&boat slip

4.97 out of 5 average rating, 38 reviews
Guest favorite
Cottage in Key West

Hidden Key West Cottage • Walk to Duval

4.85 out of 5 average rating, 40 reviews
Superhost
A bright yellow exterior of a house is seen, complemented by black shutters at the windows. A clear path of stepping stones leads towards the front door, which is framed with black security bars. Lush green grass surrounds the entrance, enhancing the home’s inviting appearance.
Cottage in Miami

Green & Gold cottage

4.59 out of 5 average rating, 34 reviews
A serene outdoor seating area is presented with two blue chairs arranged around a round white table. The peaceful waterfront view features palm trees and nearby homes along the shoreline under a clear blue sky.
Cottage in Islamorada

FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE

4.82 out of 5 average rating, 201 reviews
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

Serene Cozy Cottage in Islamorada with Heated Pool

4.8 out of 5 average rating, 91 reviews
Cottage in Key Largo

Waterfront 2 bedrooms, 1 bath Cottage Private Dock

4.6 out of 5 average rating, 5 reviews

Destinations to explore