Keewaydin Island Romantic Vacations 2026

Top Romantic vacation packages in Keewaydin Island

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

Landing Apartments Fort Myers near Olympia Pointe

$588

per person

Nov 11 - Nov 16

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

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! (1,163 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 22 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,004 reviews)

Landing Furnished Apartments Immokalee Road - Naples

Rural Estates

Save 100% on your flight

$827

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

8.4/10 Very Good! (5 reviews)

Landing Apartments Fort Myers - River District

Fort Myers River District

$661

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

7.6/10 Good! (8 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

$1,150

per person

Dec 17 - Dec 21

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

$7,156

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (38 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.

Landing Apartments Fort Myers near Olympia Pointe

$524

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

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! (1,163 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

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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 18 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (432 reviews)

The Lighthouse Resort Inn & Suites

$932

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,790 reviews)

NOT FAMILY FRIENDLY. But is a great place. Music last until 12 both nights. Tiki bar was Tiking. Tiki bar is nice. Room was clean, cold( great for Florida heat). Night stands need to be replaced. Very small. Shower was hot, when needed. Colby was wonderful!! Answered all of my questions, and was very friendly. Would stay again.

Reviewed on Oct 4, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,013

per person

Dec 29 - Jan 2

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,004 reviews)

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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?