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.

The Perry Hotel Naples

Save 100% on your flight

$483

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Everyone i was nice

Reviewed on Aug 20, 2026

Innovation Hotel

Save 100% on your flight

$919

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (632 reviews)

All was excellent..!!

Reviewed on Aug 18, 2026

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,082

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (7 reviews)

Landing Apartments Fort Myers near Olympia Pointe

Save 100% on your flight

$716

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

Wiggins Pass Chalet

$648

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (281 reviews)

Overall it was an awesome stay.

Reviewed on Aug 16, 2026

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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

$1,457

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! (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

Save 100% on your flight

$2,187

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (28 reviews)

Best luxury hotel in Naples

Reviewed on Aug 15, 2026

The Ritz-Carlton Naples, Tiburón

$1,656

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Perry Hotel Naples

Save 100% on your flight

$429

per person

Oct 5 - Oct 8

found 19 hours ago

Roundtrip flight included

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

9.6/10 Exceptional! (992 reviews)

Everyone i was nice

Reviewed on Aug 20, 2026

Bellasera Resort

Old Naples

Save 100% on your flight

$708

per person

Oct 5 - Oct 8

found 19 hours ago

Roundtrip flight included

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

9.6/10 Exceptional! (2,310 reviews)

Very clean, and accessible

Reviewed on Aug 16, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$552

per person

Oct 29 - Nov 1

found 3 hours ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.4/10 Exceptional! (100 reviews)

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4 Night Romantic vacations in Keewaydin Island

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

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$577

per person

Nov 10 - Nov 14

found 4 hours ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.8/10 Exceptional! (1,283 reviews)

They have a sunset cruise and a very nice mall. It's a great place.

Reviewed on Aug 18, 2026

Manasota Key Resort

Save 100% on your flight

$702

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Fort Myers (RSW)

9.4/10 Exceptional! (307 reviews)

The property need update!!

Reviewed on Aug 16, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$809

per person

Nov 2 - Nov 6

found 9 hours ago

Roundtrip flight included

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

8.6/10 Excellent! (1,005 reviews)

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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 $429. 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?