Ten Thousand Islands Luxury Vacations

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Flight and Luxury hotel deals in Ten Thousand Islands

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

CA $914
per person
Sep 16 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.8/10 Excellent! (9 reviews)
Great pool,comfortable room.

Reviewed on Mar 27, 2026

The Perry Hotel Naples

The Perry Hotel Naples

CA $1,294
per person
Oct 24 - Oct 29
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
Bellasera Resort

Bellasera Resort

Old Naples
CA $969
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (2,310 reviews)
Very nice

Reviewed on Aug 12, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $1,468
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,012 reviews)
Shell Island Beach Club

Shell Island Beach Club

East End
CA $1,469
per person
Oct 24 - Oct 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (24 reviews)
Great place to stay on the beach! Woman at the front desk was rude!

Reviewed on Jun 7, 2026

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5* Luxury holidays in Ten Thousand Islands

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

Sundial Beach Resort & Spa

Mid Island
CA $1,898
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (2,680 reviews)
Great place

Reviewed on Aug 14, 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
CA $3,572
per person
Oct 24 - Oct 29
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.6/10 Exceptional! (28 reviews)
The Ritz-Carlton Naples, Tiburón

The Ritz-Carlton Naples, Tiburón

CA $2,498
per person
Oct 24 - Oct 29
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.2/10 Wonderful! (675 reviews)
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3 Night Luxury holidays in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $831
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,012 reviews)
Bellasera Resort

Bellasera Resort

Old Naples
CA $969
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (2,310 reviews)
Very nice

Reviewed on Aug 12, 2026

The Perry Hotel Naples

The Perry Hotel Naples

CA $1,347
per person
Nov 6 - Nov 9
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
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4 Night Luxury holidays in Ten Thousand Islands

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

CA $767
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (3,145 reviews)
Always a great stay! Especially as a solo traveler!

Reviewed on Aug 14, 2026

The Perry Hotel Naples

The Perry Hotel Naples

CA $1,584
per person
Nov 4 - Nov 8
just found
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
Casa Ybel Resort

Casa Ybel Resort

Mid Island
CA $1,054
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (397 reviews)
Loved the location & the beach The only negative is that you need to pay a lot of money for the beach chairs Beautiful sunsets

Reviewed on Aug 14, 2026

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Plan the perfect luxury Ten Thousand Islands vacation with Expedia

What are some benefits when booking luxury Ten Thousand Islands vacations?

When you book a luxury Ten Thousand Islands vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Ten Thousand Islands?

If you're looking for something luxurious in Ten Thousand Islands, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $767, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 25. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Ten Thousand Islands. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Ten Thousand Islands?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Ten Thousand Islands.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Ten Thousand Islands. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Ten Thousand Islands?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Ten Thousand Islands or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Ten Thousand Islands. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

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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.