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.

Wiggins Pass Chalet

Save 100% on your flight

$575

per person

Sep 16 - Sep 23

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (281 reviews)

Overall it was an awesome stay.

Reviewed on Aug 16, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$899

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

The Perry Hotel Naples

$1,050

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$872

per person

Sep 16 - Sep 23

found 1 day ago

Roundtrip flight included

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

9.8/10 Exceptional! (7 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$867

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (87 reviews)

Only thing was the parking wasn't adequate for size of the hotel, other than that it was beautiful.

Reviewed on Aug 17, 2026

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5* Romantic vacations in Keewaydin Island

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

The Ritz-Carlton Naples, Tiburón

$1,176

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (675 reviews)

Sundial Beach Resort & Spa

Mid Island

$1,349

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,680 reviews)

This place was amazing. My son loved it, we had a wonderful time.

Reviewed on Aug 16, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

$1,577

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (28 reviews)

Best luxury hotel in Naples

Reviewed on Aug 15, 2026

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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

$683

per person

Oct 24 - Oct 27

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (975 reviews)

The Perry Hotel Naples

$1,050

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Shell Island Beach Club

East End

$789

per person

Oct 17 - Oct 20

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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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4 Night Romantic vacations in Keewaydin Island

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

South Seas

$722

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip flight included

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

8.4/10 Very Good! (1,004 reviews)

Good time, very nice mini vacation, property had a few water issues but staff responded prompt, be aware everything closes early. We ate at Harborside and food was very good, staff was very nice.

Reviewed on Aug 17, 2026

The Perry Hotel Naples

Save 100% on your flight

$896

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Tween Waters Island Resort & Spa

$871

per person

Oct 29 - Nov 2

found 2 hours ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Clean and quiet rooms, right on the beach.

Reviewed on Aug 16, 2026

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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.

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 $575. 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.

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?