Keewaydin Island Romantic Vacations 2026

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Top Romantic vacation packages in Keewaydin Island

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

Doubletree by Hilton Fort Myers at Bell Tower Shops

Villas

Save 100% on your flight

$577

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,180 reviews)

Overall great place for the value. I love the location and the walkability to restaurants and bars. This was my 2nd time staying here and I wouldn't mind staying every time we come to Fort Myers. The pool is nice too.

Reviewed on Aug 22, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,196

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,048 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$825

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (975 reviews)

Wiggins Pass Chalet

Save 100% on your flight

$777

per person

Nov 9 - Nov 16

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (281 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$821

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,009 reviews)

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5* Romantic vacations in Keewaydin Island

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

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

$1,782

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,680 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

$1,832

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (28 reviews)

The Ritz-Carlton Naples, Tiburón

$2,248

per person

Nov 9 - Nov 16

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.2/10 Wonderful! (675 reviews)

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3 Night Romantic vacations in Keewaydin Island

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

Hyatt Vacation Club at Coconut Cove, Bonita Springs

$543

per person

Sep 23 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (975 reviews)

The Perry Hotel Naples

$703

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,048 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$613

per person

Oct 26 - Oct 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (1,009 reviews)

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4 Night Romantic vacations in Keewaydin Island

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

Tween Waters Island Resort & Spa

Save 100% on your flight

$721

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,004 reviews)

The property is very nice. Its pools are very clean and the customer service is really good. The front desk is very nice, the lady who attended to us. We really felt at home. Thank you very much.

Reviewed on Aug 24, 2026

The Perry Hotel Naples

Save 100% on your flight

$800

per person

Nov 10 - Nov 14

found 17 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,048 reviews)

Casa Ybel Resort

Mid Island

$842

per person

Nov 4 - Nov 8

found 24 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

8.8/10 Excellent! (397 reviews)

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See all available trips from Columbus to Keewaydin Island

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How can I find the best Keewaydin Island vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Keewaydin Island romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .

How can I plan a great romantic trip to Keewaydin Island?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Keewaydin Island?

Put a price on love with stunning deals for duos starting at just $543. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.

Can I book Keewaydin Island spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

What’s the best time of year for a romantic vacation in Keewaydin Island?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

How can I book romantic weekend getaway packages in Keewaydin Island?

To book a loved-up break in Keewaydin Island, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Keewaydin Island with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Keewaydin Island romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?