Holiday houses in Sugarloaf Key

4.93 out of 5 average rating, 129 reviews

Cottage in Cudjoe Key

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.

Tiny home in Big Pine Key

4.81 out of 5 average rating, 195 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Top Guest favourite

Houseboat in Stock Island

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

4.8 out of 5 average rating, 271 reviews

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

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!

Top Guest favourite

Condo in Key West

4.97 out of 5 average rating, 100 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.97 out of 5 average rating, 159 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.

4.83 out of 5 average rating, 264 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!

4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

"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."

4.9 out of 5 average rating, 107 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

4.84 out of 5 average rating, 126 reviews

Apartment in Marathon

Knight's Key Suites Deluxe King Room w/ Kitchen

One-of-a-kind place accommodations located next to the 7-Mile Bridge. These rooms feature one king bed that can accommodate up to two people. The room comes equipped with a kitchen. Perfect for long or short-term stays! Knights Key Suites will be performing some concrete work to the exterior facade and adding new railings, the work will be done September 3, 2024- October 10, 2024 Monday-Friday 9:00am- 5:00pm

4.87 out of 5 average rating, 246 reviews

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath PANORAMIC Ocean Views 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, HUGE SKY Deck Rooftop Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Other great holiday rentals in Sugarloaf Key

5 out of 5 average rating, 3 reviews

Apartment in Key West

Sandbar Suite | 2 bedroom near the waterfront

TjRating, 5 stars3 weeks ago

This is a top tier Airbnb for anyone looking to have a good time in key west. It is right by a bunch of great restaurants and about a 2 minute walk from the heart of duval street. It was very clean and the host was very responsive! I will be coming back for sure!

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars2 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

4.98 out of 5 average rating, 42 reviews

Boat in Key West

Waterfront & Heated Pool - Awai's Floating Villa

ChelseaRating, 5 stars1 week ago

We stayed from Sunday to Friday and had an incredible time! The location was perfect—just a short drive to all the excitement of Key West, yet tucked away enough to feel peaceful and relaxing. The houseboat was spotless, cozy, and a perfect fit for our family of four. It had everything we needed for a comfortable stay. The resort itself was stunning, and the pool was the perfect way to unwind after a full day of exploring. The neighbors were so friendly, and the entire community had such a welcoming vibe. We would absolutely recommend this spot to anyone looking for a unique and relaxing getaway—and we’re already planning our next visit!

Home in Summerland Key

5 out of 5 average rating, 4 reviews

A month in paradise pool home.

LOUISERating, 5 stars10 months ago

We spent a month at this beautiful home. From open water the view, to the boating access, the amazing sunset and the pool, the place was perfect for us! We love the lower keys and this was the ideal place to spend a month. Tracy was always responsive answering any questions we had. I can't recommend enough. We hope to return in the future!

5 out of 5 average rating, 4 reviews

Home in Key Largo

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars2 weeks ago

Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

5 out of 5 average rating, 11 reviews

Apartment in Key West

Heron Hideaway

AllisonRating, 5 stars3 days ago

Great place to stay while in Key West far enough from Duval to be quiet yet close enough to walk to wherever you want to go. Very responsive host. The accommodations were just as pictured and described. I would recommend this place.

Houseboat in Key West

4.74 out of 5 average rating, 190 reviews

Deluxe Bungalow

BradleyRating, 5 stars3 days ago

Aqua lodges were exactly as described and just what we needed. The value was great and we had a blast staying there. Marina restaurant was really good too.