House vacation rentals in Lower Sugarloaf Key

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Top-rated house rentals in Lower Sugarloaf Key

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Guest favorite

Home in Key West

4.95 out of 5 average rating, 306 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.

Guest favorite

Home in Homestead

4.92 out of 5 average rating, 122 reviews

Charming 2BR Oasis with 2 Parking Spaces

Escape to your private oasis in a peaceful neighborhood! Enjoy the entire space, including your own entrance and easy self check-in with a lock box holding two keys. This beautifully split duplex features 2 cozy bedrooms, 1 bathroom, and a comfortable sectional that converts into a bed. The kitchenette is fully stocked with everything you need for home-cooked meals. Located just 40 minutes from Miami and 25 minutes from the Florida Keys and National Parks it’s the perfect home away from home!

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 105 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.

Guest favorite

Home in Key Largo

4.99 out of 5 average rating, 147 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 176 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Guest favorite

Home in Upper Sugarloaf Key

4.91 out of 5 average rating, 66 reviews

Lighthouse - Bungalows Sugarloaf Beach Key West

THE BEST TIME OF THE YEAR TO VISIT IS NOW!!!! TEMPERATURE IS AMAZING AND SEAWEED IS AT A MINIMUM. 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.

Guest favorite

Home in Marathon

4.94 out of 5 average rating, 157 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! 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!!

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 138 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.

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 119 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.

Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 243 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!

Guest favorite

Home in Cudjoe Key

4.92 out of 5 average rating, 155 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."

Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 108 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!