Romantic Vacations in Keewaydin Island 2026

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Flight and Romantic hotel deals in Keewaydin Island

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

Landing Apartments Fort Myers near Olympia Pointe

CA $914

per person

Sep 16 - Sep 23

found 20 hours 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

CA $1,294

per person

Oct 24 - Oct 29

found 6 hours ago

Roundtrip flight included

Hamilton (YHM) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

The hotel, accommodation, and service were excellent. The trip to the island was spectacular; that excursion, included with the stay, was very unique.

Reviewed on Aug 14, 2026

Bellasera Resort

Old Naples

CA $969

per person

Oct 2 - Oct 5

found 5 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

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

East End

CA $1,469

per person

Oct 24 - Oct 31

found 7 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* Romantic holidays in Keewaydin Island

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

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

Coquina Sands

CA $3,572

per person

Oct 24 - Oct 29

found 6 hours ago

Roundtrip flight included

Hamilton (YHM) to Fort Myers (RSW)

9.6/10 Exceptional! (28 reviews)

The Ritz-Carlton Naples, Tiburón

CA $2,498

per person

Oct 24 - Oct 29

found 6 hours ago

Roundtrip flight included

Hamilton (YHM) to Fort Myers (RSW)

9.2/10 Wonderful! (675 reviews)

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3 Night Romantic holidays in Keewaydin Island

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

CA $831

per person

Oct 1 - Oct 4

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

Bellasera Resort

Old Naples

CA $969

per person

Oct 2 - Oct 5

found 5 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

CA $1,347

per person

Nov 6 - Nov 9

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

The hotel, accommodation, and service were excellent. The trip to the island was spectacular; that excursion, included with the stay, was very unique.

Reviewed on Aug 14, 2026

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4 Night Romantic holidays in Keewaydin Island

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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

CA $767

per person

Sep 17 - Sep 21

found 20 hours 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

CA $1,203

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

The hotel, accommodation, and service were excellent. The trip to the island was spectacular; that excursion, included with the stay, was very unique.

Reviewed on Aug 14, 2026

Marco Beach Ocean Suites

South End

CA $1,937

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.8/10 Excellent! (1,458 reviews)

Everything was excellent

Reviewed on Aug 13, 2026

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What are some of the benefits of booking a romantic Keewaydin Island vacation?

When booking a romantic Keewaydin Island vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Naples.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Keewaydin Island destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Keewaydin Island?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $767 and can enjoy savings of up to 25 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Keewaydin Island?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Keewaydin Island certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Keewaydin Island.

Can I book a romantic Keewaydin Island vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Keewaydin Island search.

Can I book a romantic trip to Keewaydin Island that is fully refundable?

Several romantic Keewaydin Island vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.