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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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Cottage in Cudjoe Key

4.9 out of 5 average rating, 136 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!

Cottage in Islamorada

4.95 out of 5 average rating, 41 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

Cottage in Florida

4.82 out of 5 average rating, 175 reviews

Gateway to the Everglades, The Cottage

The Cottage is located about 45 min. South-West of Downtown Miami in the Redland Farming district along the eastern boarder of the Everglades National Park. Roughly the size of a two-bedroom apartment, it stands alone in the south-east corner of the property. Surrounded by trees, and many types of orchids, Bromeliads, and other exotic plants. Privet, and off the beaten path, the Cottage is perfect for those who wish to stay away from town, yet be close for day trips to most all attractions.

Cottage in Coral Gables

5.0 out of 5 average rating, 38 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.

Cottage in Miami

4.89 out of 5 average rating, 120 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 bedroom and a living, dining, kitchen and bath area on the first floor. Full size sofa bed suitable for 1 adult or 2 children ONLY (strictly enforced). 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.

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage. Short walk to world famous Lorelei for sunset celebrations. Custom length of stays can be arranged if booking a sandbar/sunset/fishing charter with our family business. The cottage was built in 1940s and still has the original hardwood floors, open beam ceilings. Private yet in the heart of Islamorada. Walk to two local craft breweries nearby! This listing is new to AIRBNB but booked for many reservations thru VRBO all 5 star. One pet only under 20lbs. /pet fee $150

Cottage in Miami

4.92 out of 5 average rating, 13 reviews

Cozy cottage garden & parking

Enjoy peace of mind when booking with a 4 year SuperHost Excited to introduce our newest listing! -Private & peaceful studio apt -Private outdoor sitting area -Centrally located .7 miles from Marlins Park -4 miles from Miami International & 2 miles from Bayfront Park -Plush Queen bed, crisp white sheets -Blackout curtains -Free off street private parking -Smart tv -High speed internet -Beach towels, bag & cooler -Kitchenette with cooking supplies -Early check in, late check out when possible

Cottage in Miami

4.92 out of 5 average rating, 152 reviews

Ocho Cottage Street

Cottage in backyard of Old Spanish home in tropical historic Little Havana /Shenandoah. Small and cozy with kitchenette. Most comfortable for 3 adults or family w/small kids. Q size bed in bdrm, twin daybed with trundle in small liv room. Backyard with patio table and umbrella for sitting outside.Safe, urban neighborhood .Walk to Calle Ocho , Easy drive to Brickell, Key Biscayne.Miami Beach. Family friendly and fun location for anyone. Free street parking but no campers please. No smoking!

Cottage in Key Largo

4.89 out of 5 average rating, 273 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. 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 Less than 2 miles to Bakers Cay. we are also close to the wedding venues in Key largo as well as Islamorada

Cottage in Key Largo

4.96 out of 5 average rating, 147 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!

Cottage in Islamorada

4.84 out of 5 average rating, 133 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 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!

Vacation rentals for every style

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Popular amenities for Monroe County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Cudjoe Key

4.91 out of 5 average rating, 81 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Cottage in Cudjoe Key

4.84 out of 5 average rating, 32 reviews

Tidewater Views @ Venture Out - Waterfront

Cottage in Cudjoe Key

4.61 out of 5 average rating, 94 reviews

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

Cottage in Cudjoe Key

4.71 out of 5 average rating, 120 reviews

Calypso Cottage

Cottage in Key Colony Beach

4.57 out of 5 average rating, 7 reviews

2BR dog-friendly water view stay, resort amenities

Cottage in Cudjoe Key

4.57 out of 5 average rating, 7 reviews

Walk to the Pool - Venture Out Unit 333

Cottage in Islamorada

Adorable Cottage w/ Dock, Pool & Beach!VR24-0106

Cottage in Cudjoe Key

4.83 out of 5 average rating, 84 reviews

OCEANIA... water front cottage retreat ~

Pet-friendly cottage rentals

Cottage in Miami

4.91 out of 5 average rating, 70 reviews

Cottage-Private Gated Estate w/heated Pool Near UM

Cottage in Key Largo

4.96 out of 5 average rating, 57 reviews

2 BR with private Tiki Boat dock for 25' boat max

Cottage in Key Largo

4.94 out of 5 average rating, 34 reviews

Spacious cottage in the heart of the keys

Cottage in Homestead

4.62 out of 5 average rating, 13 reviews

Large, secluded 2-bedroom house with private yard

Cottage in Marathon

5.0 out of 5 average rating, 4 reviews

Prime Location 1B/1B Home

Cottage in Miami

4.86 out of 5 average rating, 78 reviews

Tropical cottage in center grove - pet friendly

Cottage in Key Largo

4.89 out of 5 average rating, 28 reviews

Kayaking, sailing, snorkeling Free w/ Cottage

Cottage in Islamorada

4.83 out of 5 average rating, 6 reviews

Ocean Front Cottage

Private cottage rentals

Cottage in Marathon

4.96 out of 5 average rating, 23 reviews

Catch n' Relax Canalfront Cottage in Marathon

Cottage in Miami

4.63 out of 5 average rating, 304 reviews

Historic Casa Havana - Studio Cottage

Cottage in Marathon

4.96 out of 5 average rating, 25 reviews

WATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE

Cottage in Miami

4.86 out of 5 average rating, 57 reviews

The Cottage

Cottage in Key West

4.74 out of 5 average rating, 338 reviews

1 bedroom Cottage

Cottage in Key Largo

5.0 out of 5 average rating, 29 reviews

Cottage home in the heart of Key Largo

Cottage in Key Largo

5.0 out of 5 average rating, 6 reviews

Ocean Shores Cottage: Heated private Pool-OS canal

Cottage in Miami

4.83 out of 5 average rating, 70 reviews

Historic Cottage in the Heart of the Grove

Destinations to explore