"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
"We had a fantastic stay in August! The location was perfect—right on the water, with kayaks available. The bedrooms were comfortable and all had great views. Our favorite place was the tiki for morning coffee and afternoon cocktails. It was the first vacation we had in a few years, and relaxation was fulfilled by the Hemingway House and Key West!We did spend some time figuring out the HVAC system. One thermostat seemed to be the main one while the second acted as a satellite."
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
"Location was amazing. Lots of great local restaurants and food markets nearby. Property was gorgeous, very private, and spacious interiors. Beds were so comfortable! Friendly staff and the pool was a 10 out of 10!! I will be back. "
"Great location, layout of house beautiful. House run down, furniture old. Nails on the walls. Wallpaper coming up / torn. Cabinets dirty. No vaccum for getting sand up, especially for crawling baby. Not a swimming beach. Disappointed, not exceptional as marketed"
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All-inclusive Sugarloaf Key holidays: everything you need to know
Can I book Sugarloaf Key all-inclusive holidays with airfare and meals?
Use the all-inclusive filter to find amazing all-inclusive package holidays to Sugarloaf Key, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.
Why should I book a Sugarloaf Key adults-only all-inclusive holiday?
If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Sugarloaf Key and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.
Can I book last minute all-inclusive holidays to Sugarloaf Key?
Last-minute breaks are a great way to find very cheap all-inclusive holidays to Sugarloaf Key. If you can be flexible with your holiday dates, browse our best Sugarloaf Key deals and use the all-inclusive filter to add everything that makes your hols perfect.
Can I book a cheap all-inclusive Sugarloaf Key trip?
There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Sugarloaf Key. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.
What should I look for when booking a 5-star all-inclusive holiday to Sugarloaf Key?
All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.
What should I consider when booking a Sugarloaf Key all-inclusive family holiday?
If you’re holidaying with tots in tow, book an all-inclusive Sugarloaf Key package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.
How can I find the best deals on all-inclusive holidays to Sugarloaf Key in 2026/2027?
There are great all-inclusive deals galore in Sugarloaf Key. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.
Can I book an all-inclusive Sugarloaf Key package with free cancellation and/or flexible dates?
Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.
Why should I book an all-inclusive Sugarloaf Key package holiday with Expedia?
With a huge range of all-inclusive Sugarloaf Key trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.