Gasparilla Island Luxury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top Luxury holiday packages in Gasparilla Island
- Matanzas Inn Bayside Resort and Marina
15 Oct - 21 OctMatanzas Inn Bayside Resort and Marina + Flight
Fort Myers Beach6 nights3.0 star property9.4/10 - Exceptional (1,004 reviews)Return • London (LON) - Fort Myers (RSW)LHR - MIA • 2 stops MIA - LHR • 1 stop£884£712found 1 day agoper traveller - Casa Ybel Resort
15 Oct - 21 OctCasa Ybel Resort + Flight
Mid Island6 nights2.5 star property8.8/10 - Excellent (400 reviews)"Great place to stay. Always check your invoice because they had extra charges on my bill and place a huge hold on CC for deposit and takes time for return. It could be the bank too. They also charged me by error and refunded but still haven’t received after few days.the amenities were great and the beach! Also entrance with wood little bridge really scared us. I believe they fixed while we were there. Lots of bugs !! Maybe property should clean up trees and fumigate because we were bit by..."Reviewed August 5, 2026Return • London (LON) - Fort Myers (RSW)LHR - MIA • 2 stops MIA - LHR • 1 stop£1,342£945found 1 day agoper traveller - The Perry Hotel Naples
15 Oct - 21 OctThe Perry Hotel Naples + Flight
Naples6 nights4.5 star property9.6/10 - Exceptional (999 reviews)"We would definitely book this hotel again!"Reviewed August 6, 2026Return • London (LON) - Fort Myers (RSW)LHR - MIA • 2 stops MIA - LHR • 1 stop£1,318£934found 1 day agoper traveller - Marriott Sanibel Harbour Resort & Spa
15 Oct - 21 OctMarriott Sanibel Harbour Resort & Spa + Flight
Punta Rassa6 nights4.0 star property8.6/10 - Excellent (1,013 reviews)"Very clean, the room is very spacious and comfortable and the staff is super friendly, I recommend 100%"Reviewed August 5, 2026Return • London (LON) - Fort Myers (RSW)LHR - MIA • 2 stops MIA - LHR • 1 stop£1,234£963found 1 day agoper traveller - Lani Kai Beachfront Resort
15 Oct - 21 OctLani Kai Beachfront Resort + Flight
Fort Myers Beach6 nights3.5 star property8.8/10 - Excellent (1,865 reviews)"Room was in need of updating. Tiny pillows on a King bed is just wrong."Reviewed August 6, 2026Return • London (LON) - Fort Myers (RSW)LHR - MIA • 2 stops MIA - LHR • 1 stop£1,020£826found 1 day agoper traveller
Discover the most popular places to visit in Gasparilla Island
Top Luxury Gasparilla Island Hotels
The Palmetto Inn
The Palmetto Inn
Boca Grande Hotel - King Room
Boca Grande Hotel - King Room
Boca Grande Hotel - Economy King Room
Boca Grande Hotel - Economy King Room"very nice"
Boca Grande Hotel - Queen Room
Boca Grande Hotel - Queen Room"Host was very welcoming and informative about great restaurants on the island. "
Boca Grande Hotel - ADA Queen Room
Boca Grande Hotel - ADA Queen Room"Great place. The nicest receptionist ever, parking permit for the whole stay in town. Nice mini market next to the hotel, beds were really good. "
All you need to know about luxury holidays in Gasparilla Island
What can I expect from a luxury Gasparilla Island holiday?
Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.
How can I find all-inclusive luxury holidays in Gasparilla Island?
Tick the all-inclusive and 5-star filters to find the crème de la crème of Gasparilla Island holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.
Can I book a cheap luxury holiday to Gasparilla Island?
A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Gasparilla Island starting at £712. Prices and availability are subject to change. Additional terms may apply.
Are there luxury spa holidays in Gasparilla Island?
For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Gasparilla Island spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.
What should I look for when booking a luxury family holiday in Gasparilla Island?
Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.
Can I book luxury last-minute holidays to Gasparilla Island?
You can wangle a top-notch luxury holiday in Gasparilla Island for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!
Can I book a luxury holiday in Gasparilla Island with free cancellation and/or flexible dates?
If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.
Why should I book my luxury travel to Gasparilla Island with Expedia?
Nobody does luxury quite like Expedia. With so many gorgeous properties in Gasparilla Island to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.