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.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$442

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (121 reviews)

Beautiful property and amenities. Clean rooms, great food.

Reviewed on Sep 27, 2026

The Perry Hotel Naples

Save 100% on your flight

$933

per person

Dec 15 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

Every room needs a microwave

Reviewed on Sep 28, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$545

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,006 reviews)

Great place friendly staff.

Reviewed on Sep 27, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$1,135

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

This well-equipped apartment overlooks the grounds and swimming pool with views of the beach just yards away. Fully restored after the devastation from hurricane Ian 4 years ago it’s in great shape and we had a wonderful stay. The staff work tirelessly to keep the place as it should be and nothing was too much trouble. I can’t recommend it highly enough.

Reviewed on Sep 6, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$535

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

The view from our balcony was amazing, room was clean and beds were comfy. Staff were friendly. Just check your final bill carefully as we were charged for fees not previously disclosed.

Reviewed on Sep 25, 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

$845

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Beautiful room. Easily accessible to pool and beach.

Reviewed on Sep 26, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,647

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (38 reviews)

The Ritz-Carlton Naples, Tiburón

$1,359

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (681 reviews)

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3 Night Romantic vacations in Keewaydin Island

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

Landing Apartments Fort Myers near Olympia Pointe

$557

per person

Dec 3 - Dec 6

found 19 hours 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

The Perry Hotel Naples

$773

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

Every room needs a microwave

Reviewed on Sep 28, 2026

Bellasera Resort

Old Naples

$886

per person

Dec 16 - Dec 19

found 19 hours ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.6/10 Exceptional! (2,328 reviews)

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4 Night Romantic vacations in Keewaydin Island

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

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$396

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,003 reviews)

We had a great stay! The check in was easy and the hotel had plenty of parking. The hotel is centrally located with a short walk to restaurants and 5-10 minute walk to the beach. There also is a restaurant with outdoor seating overlooking the harbor where we had a nice dinner on Saturday night.

Reviewed on Sep 28, 2026

Casa Ybel Resort

Mid Island

Save 100% on your flight

$514

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (432 reviews)

Good

Reviewed on Sep 28, 2026

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$450

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 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 $396. 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?