Cottage vacation rentals in Florida Keys

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Top-rated cottage rentals in Florida Keys

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Top guest favorite

Cottage in Coconut Grove / Miami

4.9 out of 5 average rating, 379 reviews

Coconut Grove Private Garden Cottage + Parking

Escape to this charming private garden cottage in the heart of Coconut Grove in Miami’s most historic & lush neighborhood. Enjoy convenient, free gated parking, magical tropical greenery, & quiet, resort-style comfort just minutes from Biscayne Bay. Relax on the spacious deck or Tikki surrounded by nature & then retreat indoors to a fully furnished space with a well-equipped kitchen, washer/dryer, & cozy details. Walk to Downtown Grove parks, restaurants, cafés, shops, and bayfront attractions.

Guest favorite

A striking aerial view captures the distinctive guitar-shaped building of the Hard Rock Hotel, surrounded by a vibrant resort area. The sunset casts warm hues across the sky, reflecting on the tranquil water features that complement the modern architecture below.

Cottage in Hollywood

4.93 out of 5 average rating, 164 reviews

Cozy beach cottage steps away from Hollywood Beach

Experience ultimate beachside comfort. Just a 2-minute stroll from Hollywood Beach. This cute, comfy beachside cottage boasts plush beds (1 King + 1 sofa bed) and a fully-equipped kitchen. Exclusive access to the nearby private Beach makes this property a beach-lovers' treat. The location is also perfect for exploring the attractions of South Florida and is only a fifteen-minute drive to the Airport. The area is truly unbeatable for solo travelers or small groups looking for a relaxing getaway.

Guest favorite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 129 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 Naples

4.95 out of 5 average rating, 149 reviews

Tropical Cottage by the Sea- No Storm Damage

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

Guest favorite

A spacious living area is complemented by a wooden ceiling and large windows providing views of the water and surrounding greenery. Modern kitchen amenities are visible, along with a dining area furnished with stylish seating, creating a seamless indoor-outdoor experience.

Cottage in Everglades City

4.98 out of 5 average rating, 158 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

Top guest favorite

A shaded seating area under thatched roofing features comfortable, woven furniture arranged around a wooden table. The serene waterway is visible beyond, with palm trees framing the view. Soft lighting creates a cozy ambiance for relaxation at sunset.

Cottage in Key Largo

4.96 out of 5 average rating, 176 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 favorite

A well-maintained pathway leads to the entrance of a guest house, enclosed by wooden fencing and lush greenery. The clear blue sky complements the inviting outdoor space, while trees provide shade to the area.

Cottage in Homestead

4.92 out of 5 average rating, 445 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

Guest favorite

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 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

The entrance features a charming porch with a wooden chair positioned beside large glass doors. Lush palm trees frame the cottage, while a bicycle rests against the wall. The pathway is lined with colorful pavers leading towards the water view beyond.

Cottage in Goodland

4.97 out of 5 average rating, 112 reviews

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Dockage, kayaks, and bikes available.

Guest favorite

A small decorative sign is positioned on a tabletop, displaying the text 'Islamorada is My Happy Place' with a light, beach-themed design. Beside it, a carved figure of a bird shows intricate green and blue details, while a soft-glow lamp stands nearby, contributing to a cozy ambiance.

Cottage in Islamorada

4.96 out of 5 average rating, 113 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!

Guest favorite

A vibrant waterfront scene features a thatched-roof structure with several palm trees surrounding it. Jet skis are docked alongside a wooden pathway. Colorful umbrellas offer shade to seating areas, creating a welcoming atmosphere for visitors enjoying the sunny Florida weather.

Cottage in Key Largo

4.9 out of 5 average rating, 351 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

Top guest favorite

Cottage in Miami Lakes

4.98 out of 5 average rating, 223 reviews

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a kayak.