House vacation rentals in Key Haven

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Top-rated house rentals in Key Haven

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Guest favorite

Home in Key West

4.94 out of 5 average rating, 272 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Jul 25 – Aug 1

G$105,280 GYD per night

Guest favorite

Home in Key Colony Beach

5.0 out of 5 average rating, 15 reviews

Coral House: 2/2 Waterfront in KCB w/ King Beds

Dog-friendly canal-front home with waterfront patio, water views, king size beds, & a washer/dryer! Welcome to the heart of the Florida Keys. Come relax, play, and stay in Key Colony Beach. Our house is perfect for families, couples, & small groups looking to experience the Keys. Walk to nearby atttractions such as dining, live music, water sports rentals, marinas, fishing charters, private boat rentals, shopping, and more. Have a small boat or jet ski? We have a 20 foot dock that you can use.

May 13 – 20

G$31,768 GYD per night

Superhost

Home in Key West

4.89 out of 5 average rating, 27 reviews

Key West Paradise

Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

Nov 22 – 29

G$140,156 GYD per night

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Aug 11 – 18

G$83,266 GYD per night

Guest favorite

Home in Key West

5.0 out of 5 average rating, 63 reviews

Clean and Relaxing! 3 King Suites! With everything

3 rooms 3 bathrooms. linens provided. Covered garage Community pool, clubhouse, gym. Two person per room, children allowed, No PETS. There is no smoking inside house or pets. After each stay there is a 3 day window with no bookings to clean and disinfect thoroughly. Fully equipped kitchen, service for 8. Bathrooms have a shower Hose faucet handle. With 4 bath towels, 4 washcloths and 4 hand towels. 6 beach towels Shampoo/Conditioner, Bodywash, Blow-dryer. TVs & HD cable, free Wifi.

Apr 9 – 16

G$162,127 GYD per night

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 124 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Oct 10 – 17

G$80,294 GYD per night

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 107 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Sep 14 – 21

G$75,299 GYD per night

Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 222 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Aug 22 – 29

G$83,848 GYD per night

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 126 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Oct 1 – 8

G$68,095 GYD per night

Guest favorite

Home in Naval Air Station Key West

4.88 out of 5 average rating, 16 reviews

Coral Hammock Cozy Home

Coral Hammock is a gated community with a pool, clubhouse, and small gym. Short drive to everywhere in Key west including being 8-10 minutes from downtown and 4 minutes from the beach. Plenty of great restaurants right near the home like Hogfish bar and grill, El Siboney, Roostica, Perry’s, etc. The home had 3 bedrooms and 3 full bathrooms. Also has fully equipped kitchen and parking included. 2 parking spots in the community are included.

Oct 9 – 16

G$96,002 GYD per night

Guest favorite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Sep 27 – Oct 4

G$77,384 GYD per night

Superhost

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 46 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our cozy nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings relaxing and sipping your coffee or cocktails.

Feb 21 – 28

G$192,447 GYD per night