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.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

$524

per person

Dec 4 - Dec 7

found 3 hours ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.2/10 Wonderful! (3,389 reviews)

The Perry Hotel Naples

Save 100% on your flight

$642

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$4,161

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Bellasera Resort

Old Naples

Save 100% on your flight

$1,970

per person

Dec 29 - Jan 2

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (2,333 reviews)

The Bellasera never fails! I have been coming here annually for several years now. The grounds are beautiful and always well maintained. The rooms are comfortable and accommodating for parties of all sizes. The rooms add the convenience of home with the kitchens, dining area, and washer/dryer. The pool and jacuzzi are nice when it's not so crowded. There is a workout facility and restaurant on the property and beach is about a mile away. The hotel provides umbrellas and chairs for use at the beach as well as bicycle rentals. The location is great because there are plenty of restaurants and shops in walking distance or a short drive away. If you're looking for an upscale, quiet getaway in Naples, Fl; this is it! I'm a 40+ Golden Girl, living my life like it's Golden. Bellasera provides a Golden experience for singles, couples, and families of all ages.

Reviewed on Oct 3, 2026

Landing Apartments Fort Myers near Olympia Pointe

$585

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (9 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

$822

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,638

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

New York (LGA) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The Ritz-Carlton, Naples

Pelican Bay

$4,358

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (519 reviews)

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3 Night Romantic vacations in Keewaydin Island

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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

$524

per person

Dec 4 - Dec 7

found 3 hours ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.2/10 Wonderful! (3,389 reviews)

The Perry Hotel Naples

Save 100% on your flight

$642

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Sundial Beach Resort & Spa

Mid Island

$822

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keewaydin Island

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4 Night Romantic vacations in Keewaydin Island

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

Casa Ybel Resort

Mid Island

Save 100% on your flight

$657

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (439 reviews)

The Perry Hotel Naples

Save 100% on your flight

$1,020

per person

Dec 9 - Dec 13

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,013

per person

Dec 29 - Jan 2

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Don't see what you're looking for?

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 $524. 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?