Cottage holiday rentals in Key West

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Top-rated cottage rentals in Key West

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Top guest favourite

Cottage in Islamorada

4.95 out of 5 average rating, 39 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 favourite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 122 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.

Superhost

Cottage in Key Largo

4.84 out of 5 average rating, 44 reviews

Welcome to the Islands- Pool-Marina-Kayak

Across the street from the water and just a short walk to the kayak beach. Updated second bedroom with bunk beds. New AC system. On site marina with boat ramp and docks. Two person ocean kayak to explore mangrove tunnels. Water access to Gulf of Mexico, backwater & Atlantic Ocean. Large heated pool, kids pool, playground, volleyball, shuffleboard, basketball, bean bag toss, plus yard games. Laundry facility on site. John Pennekamp Coral Reef State park is right next door. 2hr drive to Key West.

Top guest favourite

Cottage in Marathon

4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Guest favourite

Cottage in Key West

5 out of 5 average rating, 31 reviews

Pete's West Cottage steps from Duval

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room has a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the pool

Superhost

Cottage in Cudjoe Key

4.86 out of 5 average rating, 37 reviews

Tidewater Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

Guest favourite

Cottage in Cudjoe Key

4.89 out of 5 average rating, 28 reviews

Conch Cabana in Paradise 23 miles outside Key West

Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Resort! Is located on a 60' wide canal, our Dock is 35’. With fish clean table, cleats, bumpers, shower and patio table with 4 chairs. 1 porch front yard and 1 Deck over looking the water. Just a few steps from the pool, hot tub , please be aware that they can close the pool and hot tub for emergency/ regular maintenance without any notice. VO Resort has a marina w/fuel, store, rec hall, tennis court. Great Restaurant near !

Guest favourite

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!

Superhost

Cottage in Key Largo

4.77 out of 5 average rating, 30 reviews

Cottage w/ Bay View FREE Kayaks, Snorkel & More

The Captain's is a cottage at Key Largo Cottages. We are located on the bay side of Key Largo near some of the best dive/snorkel sites, island excursions, bars, restaurants, & the Everglades. Experience water fun! A stay in one of our cottages comes with unlimited use of our kayaks, canoes, paddle boards, snorkel gear, fishing gear, &, of course, the use of one of our 22' sailboats, if you have recent sailing experience on keel boats! You won't find a better deal in the Keys!

Guest favourite

Cottage in Islamorada

4.96 out of 5 average rating, 110 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 Cudjoe Key

4.64 out of 5 average rating, 111 reviews

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

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Guest favourite

Cottage in Key Largo

4.94 out of 5 average rating, 77 reviews

Spacious cottage - the Calusa campground-keylargo

Comfortable and spacious cottage in the center of KEY LARGO, close to all activities, Publix, bars and restaurants. ENJOY THE BEST SUNSETS OF THE FLORIDA KEYS IN THE HAMMOCK AREA. The facility park has a heated pool, basketball court, tennis court, boat ramp, marina and a children’s playground. Calusa is conveniently located next to John Pennekamp Park, Fishing Charters, Snorkeling, Scuba Diving and some of the best Seafood restaurants in town.