Cottage vacation rentals in Monroe County

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Top-rated cottage rentals in Monroe County

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Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 59 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

Guest favorite

Cottage in Homestead

4.91 out of 5 average rating, 411 reviews

Redlands Bungalow

Newly remodeled guest house on 2 acres estate. Private entrance, yard with privacy fence and patio with gas grill and dining, all 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 45 mins 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

Guest favorite

Cottage in Islamorada

4.96 out of 5 average rating, 26 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.

Guest favorite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 101 reviews

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

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Guest favorite

Cottage in Florida

4.83 out of 5 average rating, 184 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.

Guest favorite

Cottage in Miami

4.9 out of 5 average rating, 125 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.

Guest favorite

Cottage in Coconut Grove / Miami

4.9 out of 5 average rating, 358 reviews

Coconut Grove, Miami’s Hidden Tropical Gem

Escape to an enchanting Miami oasis for the ultimate tropical retreat. Relax on a spacious deck surrounded by lush greenery. Immerse yourself in a meticulously designed space featuring cozy, fully furnished interiors, including a well-equipped kitchen and washer/dryer & hassle-free parking. Conveniently located near vibrant Downtown Coconut Grove, this slice of paradise offers easy access to Miami’s top attractions just minutes away. Enjoy a rejuvenating stay in the heart of the Magic City.

Guest favorite

Cottage in Key Largo

4.96 out of 5 average rating, 157 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

Cottage in Islamorada

4.82 out of 5 average rating, 164 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

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. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 156 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

Cottage in Miami

4.91 out of 5 average rating, 176 reviews

Ocho Cottage Street

Small cottage in backyard of Old Spanish home in tropical historic Little Havana /Shenandoah. Small and cozy with kitchenette. Comfortable for a couple, 3 adults or family w/small kids because space is small. . 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. Free street parking but no campers . No smoking!

Guest favorite

Cottage in Islamorada

4.98 out of 5 average rating, 93 reviews

2br/1ba w pool, 5 mins to beach and 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!