Cottage vacation rentals in Key West

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Top-rated cottage rentals in Key West

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Superhost

Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 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!

Nov 23 – 30

$759 per night

Guest favorite

Cottage in Islamorada

4.95 out of 5 average rating, 40 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

Dec 7 – 14

$399 per night

Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 78 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.

Mar 15 – 22

$799 per night

Guest favorite

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

Sep 6 – 13

$235 per night

Guest favorite

Cottage in Marathon

4.95 out of 5 average rating, 22 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

Jul 31 – Aug 7

$252 per night

Superhost

Cottage in Cudjoe Key

4.91 out of 5 average rating, 53 reviews

Turtle Cove Views @ Venture Out - Waterfront

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. ** TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of

Oct 19 – 26

$356 per night

Guest favorite

Cottage in Key Largo

4.96 out of 5 average rating, 55 reviews

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

ACTUAL LOCATION: within KeyLargoKampground.com Gated Community Lot #66 with BOAT DOCK for 25' OUTSIDE: ~ Large deck/ dock, Grill, Swim Ladder, tiki hut with swing and dining and Pub table. Parking for 1 truck & 1 car. ~ steps from the cottage Dock out back in 30' deep 100' wide Deep water swim canal with tropical fish along the banks, occasional Manatee, tarpon and finger mullet in cooler months. Maybe a porpoise. Kayack, board or Fish off dock. Walk to moon lit beaches in the park.

Nov 9 – 16

$251 per night

Superhost

Cottage in Islamorada

4.85 out of 5 average rating, 124 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.

Jan 16 – 23

$169 per night

Guest favorite

Cottage in Key Largo

4.94 out of 5 average rating, 32 reviews

Spacious cottage in the heart of the keys

Comfortable and spacious cottage in the center of KEY LARGO, close to all activities, Publix, bars and restaurant. 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 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. Up to 19ft boat allowed Boat rental is available

Jul 21 – 28

$252 per night

Guest favorite

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 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!

Jan 30 – Feb 6

$460 per night

Guest favorite

Cottage in Key Largo

4.89 out of 5 average rating, 38 reviews

Kampground Paradise w/ Kayaks, Heated Pool, Marina

Enjoy the ocean just steps away from Life in Paradise! This hidden gem is located in the community of Key Largo Kampground. This home has all the amenities for you to escape to the keys and soak in all that the sun and sea have to offer. The community offers a marina, heated pool, playground, two small private beaches, volleyball and basketball courts, and more! It offers ample room for boat parking, RV's, and all the toys! This is the perfect keys hideaway!

Aug 26 – Sep 2

$193 per night

Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Key Lime Cottage 2br 1ba w/pool

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!

Oct 25 – Nov 1

$314 per night