Cottage holiday 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 favourite

Cottage in Islamorada

4.97 out of 5 average rating, 89 reviews

Islamorada bungalow 2 beds & 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 favourite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 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 favourite

Cottage in Florida

4.84 out of 5 average rating, 197 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.

Top guest favourite

Cottage in Coconut Grove / Miami

4.9 out of 5 average rating, 380 reviews

Coconut Grove Top Rated Luxury Cottage w/ Parking

Experience natural luxury at this private Coconut Grove studio cottage vacation rental. Perfect for couples or solo travelers, it offers free gated parking, full kitchen, washer/dryer & a spacious deck with string lights & Bali / Costa Rican vibes. Walk to CocoWalk, marinas, bayfront parks, cafes & boutiques. Top-rated Airbnb Coconut Grove short-term rental; Central guest favorite Miami getaway & local retreat. Miami vacation rental • Boutique studio cottage • Walkable area • Parking included.

Top guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 179 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

Cottage in Miami

4.9 out of 5 average rating, 212 reviews

Ocho Cottage Street

Small cottage in backyard of Old Spanish home in tropical historic Little Havana /Shenandoah. Cozy with kitchenette. Comfortable for couple, 3 adults or family. No xtra cost for 3+ when for children. 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! Namesguests required.

Guest favourite

Cottage in Homestead

4.92 out of 5 average rating, 452 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

Cottage in Key West

5 out of 5 average rating, 4 reviews

Key West Cottage Du Soleil w/ Pool!

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book, and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

Superhost

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 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 favourite

Cottage in Islamorada

4.97 out of 5 average rating, 119 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!

Superhost

Cottage in Miami

4.89 out of 5 average rating, 143 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.

Guest favourite

Cottage in Key Largo

4.89 out of 5 average rating, 365 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