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

$676

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (292 reviews)

The Perry Hotel Naples

Save 100% on your flight

$978

per person

Dec 9 - Dec 13

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

$1,220

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$693

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,013 reviews)

This was an amazing place to stay. The staff was amazing. The rooms were clean and the amenities were great. we will definitely be returning.

Reviewed on Oct 6, 2026

Landing Apartments near Edison Park Historic District

Fort Myers River District

Save 100% on your flight

$795

per person

Dec 8 - Dec 15

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (6 reviews)

Todo bien

Reviewed on Jul 14, 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

$1,034

per person

Dec 9 - Dec 13

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

$3,143

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The Ritz-Carlton Naples, Tiburón

$3,451

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (684 reviews)

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3 Night Romantic vacations in Keewaydin Island

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

Landing Furnished Apartments Immokalee Road - Naples

Rural Estates

Save 100% on your flight

$488

per person

Dec 7 - Dec 10

just found

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

8.4/10 Very Good! (5 reviews)

The Perry Hotel Naples

Save 100% on your flight

$813

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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

$1,558

per person

Jan 2 - Jan 5

found 1 day ago

Roundtrip flight included

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

9/10 Wonderful! (1,003 reviews)

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4 Night Romantic vacations in Keewaydin Island

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

Olde Marco Island Inn and Suites

Olde Marco

Save 100% on your flight

$740

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

The Old Marco Inn has a very coastal feel. And the small shopping courtyard is really coll The Boardroom Tavern is a fun place to hang out for music and a drink.

Reviewed on Oct 4, 2026

The Perry Hotel Naples

Save 100% on your flight

$978

per person

Dec 9 - Dec 13

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

$1,220

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 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 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 $488. 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?