Ten Thousand Islands Beach Vacations 2026

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Top Beach vacation packages in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.

Landing Apartments Fort Myers near Olympia Pointe

Save 100% on your flight

$528

per person

Nov 7 - Nov 13

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

The Perry Hotel Naples

Save 100% on your flight

$811

per person

Dec 1 - Dec 5

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Shutter never works, rooftop bar staff is horrible

Reviewed on Sep 24, 2026

Wiggins Pass Chalet

Save 100% on your flight

$873

per person

Dec 1 - Dec 8

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (285 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,088

per person

Dec 1 - Dec 8

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,008 reviews)

Shell Island Beach Club

East End

Save 100% on your flight

$1,302

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

This well-equipped apartment overlooks the grounds and swimming pool with views of the beach just yards away. Fully restored after the devastation from hurricane Ian 4 years ago it’s in great shape and we had a wonderful stay. The staff work tirelessly to keep the place as it should be and nothing was too much trouble. I can’t recommend it highly enough.

Reviewed on Sep 6, 2026

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5* Beach vacations in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.

Sundial Beach Resort & Spa

Mid Island

$1,288

per person

Nov 29 - Dec 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Beautiful room. Easily accessible to pool and beach.

Reviewed on Sep 26, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$4,911

per person

Dec 1 - Dec 8

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Excellent!

Reviewed on Sep 23, 2026

The Ritz-Carlton, Naples

Pelican Bay

$4,332

per person

Dec 1 - Dec 8

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (513 reviews)

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3 Night Beach vacations in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$602

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

The view from our balcony was amazing, room was clean and beds were comfy. Staff were friendly. Just check your final bill carefully as we were charged for fees not previously disclosed.

Reviewed on Sep 25, 2026

The Perry Hotel Naples

$1,108

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Shutter never works, rooftop bar staff is horrible

Reviewed on Sep 24, 2026

Sundial Beach Resort & Spa

Mid Island

$967

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Beautiful room. Easily accessible to pool and beach.

Reviewed on Sep 26, 2026

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4 Night Beach vacations in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.

Tween Waters Island Resort & Spa

Save 100% on your flight

$671

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

The Perry Hotel Naples

Save 100% on your flight

$811

per person

Dec 1 - Dec 5

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Shutter never works, rooftop bar staff is horrible

Reviewed on Sep 24, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,099

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Fort Myers (RSW)

9/10 Wonderful! (1,008 reviews)

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How do I book the best Ten Thousand Islands beach vacation packages?

Life’s a beach when you dive into our brilliant Ten Thousand Islands beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Ten Thousand Islands?

A rental steps from the shore creates an amazingly affordable Ten Thousand Islands beach vacation. Seaside sojourns during low season start from $528. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Ten Thousand Islands?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Ten Thousand Islands beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Ten Thousand Islands vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Ten Thousand Islands beach vacation deals?

Sort your search results by deals to delight in amazing Ten Thousand Islands beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Ten Thousand Islands beach trip with free cancellation and/or flexible dates?

Just like the Ten Thousand Islands tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Ten Thousand Islands beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Ten Thousand Islands. (OK, maybe not that last part.)

Top Beach Ten Thousand Islands Hotels

Extraordinary view, unlike any other on Marco Island! Direct access & unique wildlife

Marco Island FL

39 min drive from Gulf Coast Visitor Center

Make the most of this fantastic location, as you'll be not far from the beach with a vacation at this vacation home.

9.2/10 Wonderful! (64 reviews)

Travelers like: close to beach, private pool

Travelers say...

"Really this is a wonderful house, location and host. The only thing I would add is that the house need some small repairs but overall 5 stars."

Reviewed on Jun 21, 2026

Waterfront 3-BR, 2-BA Pet Friendly Vacation Rental 5 mi to Marco Island

Marco Island FL

34 min drive from Gulf Coast Visitor Center

Watch the sunset on the beach in Goodland, as you'll be not far from the beach with a holiday at this vacation home. Beach towels and sun loungers are just a ...

Stunning Estate Minutes to 10,000 Islands ~ Luxurious Waterfront w/Pool, Spa, Outdoor Living & More

Marco Island FL

40 min drive from Gulf Coast Visitor Center

Stay at this vacation home in Marco Island. Enjoy free WiFi, private pools, and patios. Popular attractions Marco Beach and Otter Mound Preserve are located ...

10/10 Exceptional! (2 reviews)

Great Experience

"This was our first vacation using iTrip. Everything was above and beyond our expectations. From the welcome basket, to the friendly reminders about trash and recycling and occasionally checking in to see how everything was on the property. There even was a bin of fire wood, log starter and lighter ..."

Reviewed on Apr 14, 2026

See all 6,443 properties in Ten Thousand Islands

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.