Title: Keewaydin Island Romantic Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6337231/0b8ef5b6-2083-4cdb-97c8-d4b5fcbc1cee.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Keewaydin Island Romantic Vacations ## Book a Romantic Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Romantic vacation packages in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Hyatt Vacation Club at Coconut Cove, Bonita Springs](https://images.trvl-media.com/lodging/1000000/1000000/991200/991114/fedffc57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Coconut Cove, Bonita Springs $828 per person May 22 - May 25 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The pools and Lazy river was awesome. Condos a little outdated but nice Reviewed on Mar 3, 2026 ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples Save 100% on your flight $979 per person May 6 - May 13 found 21 hours ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Such a beautiful hotel! Both the rooftop and outside pool were heated and absolutely delightful! They have a boat that will take you down the river and drop you off at Barefoot Beach. You can stay as long as you like as boat comes back every hour. The food at the rooftop restaurant (The Tigress) was one of the best dinners we’ve had in a long time! Highly recommend this hotel! Will be coming back! Reviewed on Mar 4, 2026 ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/0ef86cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa Save 100% on your flight $890 per person May 21 - May 26 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) Unfortunately we had the unpleasant experience of staying at the Captiva Tower. So, no the pool was not enjoyable because of the sewer smell coming from the parking lot. I spoke to management and they did apologize for the lack of service, amenities and cleanliness of Captiva Tower and did refund some of our money. So, staff are great at the front desk. Reviewed on Mar 3, 2026 ![Bellasera Resort](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/0dfad72d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bellasera Resort Old Naples Save 100% on your flight $1,465 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (2,246 reviews) Love it, best in the area Reviewed on Mar 5, 2026 ![Hilton Naples](https://images.trvl-media.com/lodging/1000000/450000/448200/448199/a9bd1057_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Naples Park Shore Save 100% on your flight $967 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (1,376 reviews) Very nice hotel? Quite and clean room. Me and my wife enjoyed our stay Reviewed on Feb 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-06/2026-04-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic vacations in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Sundial Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/2000/1939/f4e5c65a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island Save 100% on your flight $1,253 per person May 21 - May 26 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.6/10 Excellent! (2,600 reviews) The room was good condition, we enjoyed the pickleball courts. The food was pricey and just so so quality. Reviewed on Mar 1, 2026 ![The Ritz-Carlton, Naples](https://images.trvl-media.com/lodging/1000000/20000/10500/10494/a86bcec0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Naples Pelican Bay Save 100% on your flight $6,539 per person Apr 19 - Apr 26 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (467 reviews) Loved everything about this hotel, the people, the room, the amenities, all of it was top notch. No complaints whatsoever. Reviewed on Jan 23, 2026 ![The Ritz-Carlton Naples, Tiburón](https://images.trvl-media.com/lodging/1000000/790000/788300/788295/a653a1be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton Naples, Tiburón $4,310 per person Apr 19 - Apr 26 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Fort Myers (RSW) 9.4/10 Exceptional! (620 reviews) Very nice accomodations. Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-06/2026-04-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic vacations in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Hilton Naples](https://images.trvl-media.com/lodging/1000000/450000/448200/448199/a9bd1057_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Naples Park Shore $511 per person May 15 - May 18 found 16 hours ago Roundtrip flight included New York (JFK) to Fort Myers (RSW) 9.2/10 Wonderful! (1,376 reviews) Very nice hotel? Quite and clean room. Me and my wife enjoyed our stay Reviewed on Feb 27, 2026 ![Hyatt Vacation Club at Coconut Cove, Bonita Springs](https://images.trvl-media.com/lodging/1000000/1000000/991200/991114/fedffc57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Coconut Cove, Bonita Springs $828 per person May 22 - May 25 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The pools and Lazy river was awesome. Condos a little outdated but nice Reviewed on Mar 3, 2026 ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples $974 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Such a beautiful hotel! Both the rooftop and outside pool were heated and absolutely delightful! They have a boat that will take you down the river and drop you off at Barefoot Beach. You can stay as long as you like as boat comes back every hour. The food at the rooftop restaurant (The Tigress) was one of the best dinners we’ve had in a long time! Highly recommend this hotel! Will be coming back! Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-06/2026-04-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic vacations in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Courtyard by Marriott Fort Myers Cape Coral](https://images.trvl-media.com/lodging/1000000/30000/22400/22386/ffbd89e9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Fort Myers Cape Coral $284 per person May 15 - May 19 found 8 hours ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.2/10 Very Good! (1,002 reviews) Staff was great and pool was relaxing. Reviewed on Mar 4, 2026 ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/0ef86cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa Save 100% on your flight $656 per person May 15 - May 19 found 8 hours ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) Unfortunately we had the unpleasant experience of staying at the Captiva Tower. So, no the pool was not enjoyable because of the sewer smell coming from the parking lot. I spoke to management and they did apologize for the lack of service, amenities and cleanliness of Captiva Tower and did refund some of our money. So, staff are great at the front desk. Reviewed on Mar 3, 2026 ![Hilton Marco Island Beach Resort and Spa](https://images.trvl-media.com/lodging/1000000/20000/17600/17575/65dd4041_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Marco Island Beach Resort and Spa South End Save 100% on your flight $704 per person May 27 - May 31 just found Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9/10 Wonderful! (1,714 reviews) We had an excellent stay! The property is very nice. Great beach, pool, restaurant, etc. The property is nicely located across the street from several very nice restaurants and retail. Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-06/2026-04-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Keewaydin Island vacation #### 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 $284\. 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? ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://expedia.com/Keewaydin-Island-Hotels.d6337231.Travel-Guide-Hotels)[ Vacation Rentals in Keewaydin Island ](https://expedia.com/Keewaydin-Island-Vacation-Rentals.d6337231.Travel-Guide-VacationRentals)[ Car Rentals in Keewaydin Island ](https://expedia.com/Car-Rentals-In-Keewaydin-Island.d6337231.Car-Rental-Guide)[ Keewaydin Island Vacations ](https://expedia.com/Keewaydin-Island.d6337231.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app