Sugarloaf Key Luxury Vacations
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Top Luxury vacation packages in Sugarloaf Key
- Cavalier Hotel South Beach
Sep 5 - Sep 9Cavalier Hotel South Beach + Flight
South Beach4 nights3.5 star property8.6/10 - Excellent (1,018 reviews)"Beautiful boutique hotel in Ann excellent location"Reviewed August 6, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - Casablanca Miami Beach
Sep 10 - Sep 14Casablanca Miami Beach + Flight
North Beach4 nights3.0 star property5.8/10 - (327 reviews)"Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No..."Reviewed July 23, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • 1 stop$9,469$4,160found 12 hours agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Oct 10 - Oct 14The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach4 nights5.0 star property8.0/10 - Very Good (1 review)"Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."Reviewed June 22, 2016Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop$14,117$6,755found 1 day agoper traveler - Luxuri Suites
Sep 7 - Sep 11Luxuri Suites + Flight
South Beach4 nights3.0 star property6.8/10 - (57 reviews)"Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work."Reviewed July 9, 2026Roundtrip • New York (EWR) - Miami (MIA)EWR - FLL • Nonstop MIA - EWR • Nonstop - Omni Fort Lauderdale Hotel
Oct 8 - Oct 12Omni Fort Lauderdale Hotel + Flight
East Fort Lauderdale4 nights4.0 star property9.6/10 - Exceptional (547 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • 1 stop
What to do in Sugarloaf Key
Private Luxury Sandbar Excursion
Marathon Backcountry Fishing Charter
Luxury Sandbar and Snorkeling trip in Key West
Top Luxury Sugarloaf Key Hotels
"The food was good! Definitely needs updating"
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views"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."
Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning Views"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!"
The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key West"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."
All you need to know about luxury vacations in Sugarloaf Key
What can I expect from a luxury Sugarloaf Key vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Sugarloaf Key vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.
How can I find all-inclusive luxury vacation packages in Sugarloaf Key?
By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.
Can I book a cheap Sugarloaf Key luxury vacation?
Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $347. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Sugarloaf Key?
Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.
Can I book a package in Sugarloaf Key with a luxury vacation home?
A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.
How can I find the best luxury vacation deals in Sugarloaf Key?
Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.
Can I book a luxury holiday in Sugarloaf Key with free cancellation and/or flexible dates?
Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.
Why should I book my luxury trip to Sugarloaf Key with Expedia?
A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.