We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Sugarloaf Key Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    AU$202 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Sugarloaf Key is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 57 Rentals in Sugarloaf Key
    Sort by:
    Default
    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 27
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Stylish, dog-friendly condo with shared pool, hot tub, and complimentary shuttle1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!1 / 26
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also welcome to join you for...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and the fresh ocean air of...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!1 / 26
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire complex for our wedding. While my husband and I did not stay in this particular cottage we did see the interior and this was used as my "bridal...
    Reviewed 22 May 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with...
    See all reviews
    About this property
    Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Cheery beach getaway near local attractions, w/shared pool & easy beach access1 / 56
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Terrace
    • Parking
    • Internet Access
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed 12 May 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
    See all reviews
    About this property
    Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick five minute walk...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue waters, warm winds, and the Florida sun await when you book a stay in this delightful two-bedroom condo with a private patio and heated community pool! Conveniently located just a few minutes from the Key West International Airport, this rental is part of the beautifully landscaped Sunset...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed 13 March 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
    See all reviews
    About this property
    Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two blocks from Fort Zachary Taylor...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Sugarloaf Key rentals sent straight to your email!
    Get the List
    Cute, dog-friendly condo w/ free shuttle, private patio, shared pool and hot tub1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Parking
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay cool on your next trip to Key West with a stay at this delightful condo with a private balcony, a shared pool, and a complimentary shuttle between the rental and many of Key West's popular attractions. Located just minutes away from beaches, marinas, scuba shops, and the Key West...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private heatedpool, luxurious patio area, covered...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Dog-friendly condo w/private hot tub & shared pool - walk to Duval St!1 / 30
    (36)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 March 2016
    My husband and I stayed at this condo for 2 nights with another couple. The location was great. Although we were near the main street, this unit (R9) was quiet (except for the...
    Reviewed 20 January 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    See all reviews
    About this property
    Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens, this Duval Square condo...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise awaits when you book your next Florida vacation at this lovely two-bedroom condo on the sunny shores of Key West. With lush tropical landscaping and exclusive resort amenities like a pool, hot tub, and tennis courts, you'll never want to leave! This rental is located in the upscale resort...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Quiet, dog-friendly getaway in a residential neighborhood with a shared pool1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this cottage but our guests had rave reviews and I...
    Reviewed 6 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
    See all reviews
    About this property
    Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Grill
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed for a small nightly fee....
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd prefer some shopping and...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Parking
    • Terrace
    • Patio
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed 11 November 2014
    This place was perfect for what we were looking for:Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
    See all reviews
    About this property
    Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana Foster's Guest House,...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Patio
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West home is waiting for you and your group of up to nine to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner at Salute, then...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    Welcoming, budget-friendly studio w/ shared heated pool & home comforts1 / 25
    (1)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2016
    If you stay here.. take your bags and lock the vehicle. I had my bag stolen from car as we took some bags to the room upon check in. Had to buy new clothes and lost cash and...
    See all reviews
    About this property
    See the best of Key West without breaking the bank when you book this cozy main-floor studio, which includes access to a shared heated pool and an unbeatable location in the heart of the city. Famous Duval Street - home to nightclubs, restaurants, stores, and more - is just two blocks away, as is...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Dog-friendly condo w/ scenic views, shared pool & hot tub, balcony & parking1 / 25
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2016
    My boyfriend and I checked in with another couple for a little under a week. The room was clean and was located within 5 miles of Duval Street. We all had a great time!
    Reviewed 31 May 2016
    We booked this with friends through trip advisor and really enjoyed our 1 night stay, rooms were spacious and comfortable with all mod cons and there was a great pool area.
    See all reviews
    About this property
    Pamper yourself with a stay in this luxurious and sunny Key West condo. Surrounded by beautiful tropical landscaping, and boasting resort amenities like a pool, hot tub, tennis courts and a private balcony with views of the Salt Ponds Preserve, this comfortable rental will have you relaxed and...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury and convenience combine in this recently renovated one-bedroom, one-bathroom condo in Key West. You'll love the shared pool, full kitchen, and various entertainment close to all the excitement of downtown! Sitting on the uppermost floor of a building surrounded by palm trees, you'll...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Grill
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sip a mug of coffee on the balcony as you take in views of the Florida sunrise at this superb Key West condo. Complete with luxurious amenities like a community pool and hot tub, a private parking space, and a dog-friendly policy, this wonderful vacation rental is sure to delight. The condo is...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Grill
    • Balcony
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2015
    We found the unit was as advertised, and clean, quiet, and comfortable. Most things worked well, though one of the locks on the door didn't work, and the lock on the patio door...
    See all reviews
    About this property
    Get your next great vacation started with this dog-friendly Florida home! All of Key West's most amazing sights are yours to experience, with plenty of amenities awaiting you at home. Courtesy Shuttle available to condo from airport and ferry terminal. Soak in the shared hot tub, or swim in the...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style during your visit to Key West - this home offers a private parking spot, an upstairs deck, dog-friendly accommodations, and plenty of space for your group to relax. Enjoy a full kitchen, free WiFi, and a pull-out bed at Duval Delight. At this home, you're on the end of historic Duval...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Parking
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly home in Key West offers swimming, sunshine, and access to sandy shores. Courtesy Shuttle available to condo from airport and ferry terminal. A free, off-street parking spot is available with your rental. Resort amenities like a shared pool and hot tub let you spend your...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2014
    We had a great night at sunrise suites. It is not central, so you have to get a taxy to go downtown. Because you have a sunset drink, wine with dinner and one before going...
    See all reviews
    About this property
    Watch the sunset from the comfort of your private balcony at this lovely Key West condo. You'll also be treated to superb resort amenities like a shared pool and hot tub, tennis courts, and lush tropical landscaping, making this rental a sure bet for a luxurious Caribbean getaway. This condo is...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful views, resort amenities, and a dog-friendly policy await when you book your stay at this charming condo on the eastern shore of Key West! Located within the upscale Sunrise Suites Resort community, this excellent rental is perfectly situated for you to explore Key West by day and relax...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Hot Tub
    • Balcony
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it...
    See all reviews
    About this property
    Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember. Located in the upscale Sunrise Suites...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Sunny tropical condo with a shared pool, close to all of the beachside action1 / 28
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Parking
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 November 2012
    Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St...
    Reviewed 7 February 2011
    Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
    See all reviews
    About this property
    Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no shortage of attractions to...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Studio condo w/ entertainment, full kitchen & private parking - central location1 / 21
    (27)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2015
    Loved this condo for our Keys getaway!! This place was perfect for our 5 day getaway and it's just 2 blocks from Duval. Very easy check in process took maybe 5 min at the most...
    Reviewed 20 August 2015
    We have stayed at Courtney's Place and another place farther down on Duval in the past. Hibiscus is closer to the "action" on Duval. Hibiscus is a unit for 2 people...
    See all reviews
    About this property
    Relaxation will come easy at this studio condo in Key West. With a calming interior, entertainment, and an awesome location with a private parking spot (with off-street parking) close to all the action, this getaway will be one to remember! Located in a historic building just one block from...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Lovely room in historic bed & breakfast w/ shared pool & a semi-private balcony1 / 24
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    Clean, nice neighborhood. Lot's of Florida Key charm. Great location and close to Duvall street and far enough away to enjoy a quiet evening by the pool. Street parking can...
    See all reviews
    About this property
    Get the most out of your vacation days when you book this charming room at the historic Curry House Bed and Breakfast. With room for two and access to a shared pool, this vacation rental is perfect for a quick weekend getaway, a weeklong romantic retreat, and everything in between! When you stay...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!1 / 24
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    Reviewed 13 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking.Cons - across...
    See all reviews
    About this property
    Located right in the heart of Key West, this tastefully-appointed, tropical sanctuary comes with a private swimming pool, enclosed yard, and room for up to six guests. The family dog is also welcome to join you for an additional nightly fee. Take a stroll down to Duval Street and enjoy the many...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 May 2016
    Sandy and her team at Curry House are friendly, helpful and welcome you to the B & B with a warm smile and they give you a hug when you leave. I went with my partner and our...
    See all reviews
    About this property
    A fun-filled Key West getaway for two starts with this lovely room in the historic Curry House Bed & Breakfast. Cozy and comfortable, the room includes access to a shared pool as well as a semi-private balcony, which faces the street toward the front of the home. Curry House is located in a quiet...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Yes, it's located 2-3 blocks South of Duval Street, nearer the Southern-most point end, and it was walkable to everywhere for us, and better on bikes, but I just couldn't get...
    Reviewed 8 October 2014
    The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors...
    See all reviews
    About this property
    This dog-friendly Key West gem offers a palm-covered patio and grill area, a kitchenette, free WiFi, and street parking! Plus, you're walking distance from the beach, historic landmarks, and local dining. Walk a half mile to the beach and enjoy Key West's legendary white sand and turquoise water!...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Enquiry
    Cottage w/ shared pool, private hot tub, & street parking - Dogs OK!1 / 27
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Terrace
    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2016
    This quaint villa was perfect for our party of 2 (might be a bit crowded for 4 adults, but for 2 kids it should be just fine!) The 1/1 was well appointed with everything we...
    Reviewed 22 September 2015
    We loved our stay here. It was decorated nicely, clean, and quiet. Housekeeping came in daily and did a good job. I liked the setup of the condo a lot; a nice, spacious...
    See all reviews
    About this property
    Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least...
    Reviewed 23 December 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style...
    See all reviews
    About this property
    Absolutely ideal for a romantic getaway for two, this cozy studio offers a well-equipped kitchenette, a furnished deck, and access to a shared swimming pool at the heart of a beautifully-maintained tropical courtyard. Located just a block from Duval Street, the hottest street in Key West,...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy and compact, this recently renovated attic room in the historic Curry House Bed & Breakfast is perfect for two guests traveling on a budget. This room includes access to the shared backyard pool, air conditioning, and typical home comforts - everything you need for the vacation of a lifetime....
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Internet Access
    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2014
    Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each...
    See all reviews
    About this property
    Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to join you...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
    See all reviews
    About this property
    Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. Courtesy Shuttle available to condo from airport and ferry terminal. A private parking spot is...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Spacious main-floor suite w/ private patio & easy access to shared heated pool!1 / 9
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2016
    Very private room with a nice patio, only steps away from the pool, which unfortunately we didn't get to use much as there was some kind of work being done in the pool area...
    See all reviews
    About this property
    One of the most in-demand rooms at the Garden House Bed & Breakfast, the Royal Poinciana feels secluded thanks to its private patio and its quiet location at the end of the house. It's perfect for a couple on a romantic retreat or a solo traveler hoping to enjoy some peace and solitude on their Key...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for a romantic getaway to Key West, this cozy, tropical-themed studio offers a shared swimming pool, outdoor seating and dining areas, a sun deck, and convenient access to exciting destinations like Duval Street, marinas, historic landmarks, and local beaches. The Garden House offers private,...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Key West paradise with shared pool - close to shops, restaurants, and beaches1 / 30
    (1)Terrible
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for a romantic getaway or a small family vacation for four, this adorable Key West studio with side-by-side beds offers a shared, heated pool, outdoor seating and dining areas, and a well-maintained courtyard. This home also offers private parking for an additional fee. Just a couple of...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Make Enquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're planning a Key West vacation for yourself or your sweetheart, you can't go wrong with this charming suite in the heart of the city. Whether you're lounging by the shared pool, soaking up the sun on the semi-secluded second-floor sun deck, or relaxing in your room, you're sure to enjoy...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Balcony
    • Parking
    • Terrace
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your family, friends, dog (for a small nightly fee) and golf clubs along for a stay in this lovely two-bedroom, one-and-a-half-bathroom home! A great location near the golf course, along with plenty of amenities (including a shared pool), ensure this will be a vacation to remember. Your new...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while...
    Reviewed 2 December 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
    See all reviews
    About this property
    Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you right in the middle of the action while surrounding you with relaxation, this home offers room for two and street parking for convenience. Located just a block from the...
    View all property information
    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    1
    List your property
    Owner log in