Chokoloskee Island Beach Holidays

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Top flight + Beach hotel deals in Chokoloskee Island

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Fort Myers near Olympia Pointe

Landing Apartments Fort Myers near Olympia Pointe

£539
per person
2 Jan - 7 Jan
found 1 day ago
Return flight included
New York (NYC) to Fort Myers (RSW)
8.8/10 Excellent! (9 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
£1,565
per person
28 Dec - 2 Jan
found 16 hours ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.6/10 Exceptional! (1,182 reviews)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
£1,495
per person
2 Jan - 7 Jan
found 1 day ago
Return flight included
New York (NYC) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

£1,308
per person
28 Dec - 2 Jan
found 16 hours ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.4/10 Exceptional! (123 reviews)
Landing Apartments Fort Myers - River District

Landing Apartments Fort Myers - River District

Fort Myers River District
£561
per person
2 Jan - 7 Jan
found 1 day ago
Return flight included
New York (NYC) to Fort Myers (RSW)
7.6/10 Good! (8 reviews)
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5* Beach holidays in Chokoloskee Island

Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
£1,646
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
8.6/10 Excellent! (2,703 reviews)
Gotta get rid of the sand chiggers.

Reviewed on 17 Oct 2026

The Ritz-Carlton, Naples

The Ritz-Carlton, Naples

Pelican Bay
£4,061
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.2/10 Wonderful! (520 reviews)
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Find your perfect Chokoloskee Island beach holiday

How can I book the best beach holidays in Chokoloskee Island?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Chokoloskee Island beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in Chokoloskee Island?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Chokoloskee Island beach holidays, which start from £539. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in Chokoloskee Island?

Enjoy out-of-season seclusion on a beach holiday to Chokoloskee Island during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in Chokoloskee Island with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a Chokoloskee Island beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute Chokoloskee Island beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in Chokoloskee Island. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find Chokoloskee Island beach holidays which are all inclusive?

A beach holiday to Chokoloskee Island is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a Chokoloskee Island beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a Chokoloskee Island beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Chokoloskee Island on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.