Southwest Florida Romantic Vacations
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Top Romantic vacation packages in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
Naples Bay Resort & Marina
Oyster Bay
Price was $701, price is now $591 per person
$591
per person
May 27 - May 30
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
Room was amazing, Every staff member was professional, knowledgeable, and very friendly….particularly the shuttle drivers! They were outstanding.
Reviewed on Apr 26, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,936, price is now $1,102 per person
$1,102
per person
May 27 - May 31
found 5 hours ago
Roundtrip flight included
New York (NYC) to Fort Myers (RSW)
9/10 Wonderful! (1,007 reviews)
Great boutique resort. Had the perfect babymoon.
Reviewed on Apr 25, 2026
Pink Shell Beach Resort and Marina
Price was $1,042, price is now $828 per person
$828
per person
May 27 - May 31
found 20 hours ago
Roundtrip flight included
Cincinnati (CVG) to Fort Myers (RSW)
9.4/10 Exceptional! (1,319 reviews)
Wonderful stay overall. Breakfast buffet was tasty, staff was always attentive, abundant wait staff, beautiful views, adults only pool, and although a resort, didn’t feel penned in.
Reviewed on Apr 24, 2026
Bellasera Resort
Old Naples
Price was $911, price is now $796 per person
$796
per person
Jun 27 - Jun 30
found 4 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Fort Myers (RSW)
9.6/10 Exceptional! (2,267 reviews)
Highly recommend! Super clean and nicely decorated. Great location — walk 5th Ave!
Reviewed on Apr 12, 2026
Inn on Fifth
Old Naples
Price was $699, price is now $615 per person
$615
per person
May 27 - May 30
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
9.4/10 Exceptional! (1,002 reviews)
Everything was perfect but the night supervisor Susana was very rude. Apparently she doesn’t like her job. All the other staff members were very helpful and very attentive.including Armand the concierge who provided a very good service. I hope the management can hire people who actually likes the job and has the correct attitude. Susana seems to be very unhappy with her work but also with her life.
Reviewed on Apr 20, 2026
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See all available trips from Columbus to Southwest Florida
View all trips5* Romantic vacations in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Sarasota
Central Sarasota
Price was $774, price is now $704 per person
$704
per person
May 27 - May 29
found 8 hours ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Professional, friendly and knowledgeable staff. I was impressed to see many of the same staff from my visit four years ago, including vallet, Bellman, food service, and concierge. This says that the Ritz Carlton treats their employees well and in turn their customer service is top notch.
Reviewed on Apr 17, 2026
Sundial Beach Resort & Spa
Mid Island
Price was $1,322, price is now $1,200 per person
$1,200
per person
Jun 27 - Jul 1
found 9 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Fort Myers (RSW)
8.6/10 Excellent! (2,627 reviews)
Very family oriented resort. Lots of daily art activities and games at main pool.
Lots of shells ( think quantity over quality), good to bring water shoes if swimming in gulf.
Room cleaning is every 3 days but you can ask the resort for anything you need.
There is one quieter pool for more of an adult atmosphere.
Overall, the resort was nice for a two bedroom, two bath with kitchen stay.
Be sure to stop by Marketplace for a coffee and the wonderful staff inside.
The island itself seems to be short- staffed and flustered.
Reviewed on Apr 25, 2026
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See all available trips from Columbus to Southwest Florida
View all trips3 Night Romantic vacations in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
Naples Bay Resort & Marina
Oyster Bay
Price was $701, price is now $591 per person
$591
per person
May 27 - May 30
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
Room was amazing, Every staff member was professional, knowledgeable, and very friendly….particularly the shuttle drivers! They were outstanding.
Reviewed on Apr 26, 2026
Pink Shell Beach Resort and Marina
Price was $914, price is now $744 per person
$744
per person
Jun 27 - Jun 30
found 3 hours ago
Roundtrip flight included
New York (NYC) to Fort Myers (RSW)
9.4/10 Exceptional! (1,319 reviews)
Wonderful stay overall. Breakfast buffet was tasty, staff was always attentive, abundant wait staff, beautiful views, adults only pool, and although a resort, didn’t feel penned in.
Reviewed on Apr 24, 2026
The Ritz-Carlton, Sarasota
Central Sarasota
Price was $1,294, price is now $1,082 per person
$1,082
per person
Jun 27 - Jun 30
found 2 hours ago
Roundtrip flight included
Washington (DCA) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Professional, friendly and knowledgeable staff. I was impressed to see many of the same staff from my visit four years ago, including vallet, Bellman, food service, and concierge. This says that the Ritz Carlton treats their employees well and in turn their customer service is top notch.
Reviewed on Apr 17, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southwest Florida
View all trips4 Night Romantic vacations in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,936, price is now $1,102 per person
$1,102
per person
May 27 - May 31
found 5 hours ago
Roundtrip flight included
New York (NYC) to Fort Myers (RSW)
9/10 Wonderful! (1,007 reviews)
Great boutique resort. Had the perfect babymoon.
Reviewed on Apr 25, 2026
Turtle Beach Resort
Save 100% on your flight
Price was $1,755, price is now $1,226 per person
$1,226
per person
May 27 - May 31
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
8.8/10 Excellent! (344 reviews)
Enjoyed our quiet and comfortable stay at Turtle Beach Resort. The staff were warm, attentive, and proactive.
The property is charming and secluded, at the end of a key and right on the edge of a serene bay with shared amenities like the pool, grill, kayaks, fishing gear, and hammocks. There are several restaurants within walking distance and a shuttle that takes you into town for even more options.
The room itself had a rustic beach cabin feel, with a well-stocked kitchen area and bathroom.
Reviewed on Apr 23, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southwest Florida
View all tripsHow to find a romantic Southwest Florida vacation
How can I find the best Southwest Florida 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 Southwest Florida 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 Southwest Florida?
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 Southwest Florida?
Put a price on love with stunning deals for duos starting at just $591. Prices and availability are subject to change. Additional terms may apply.
Can I book Southwest Florida 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 Southwest Florida?
To book a loved-up break in Southwest Florida, 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 Southwest Florida 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 Southwest Florida 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?
Top Romantic Southwest Florida Hotels
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
Al fresco dining, a hot tub, and luxury bedding await couples visiting this romantic resort. The property also offers 3 outdoor pools, a bar, and a beachfront ...
9.4/10 Exceptional! (1,330 reviews)
Couples like: beachfront dining, hot tub, on the beach
Travelers say...
Wonderful stay overall. Breakfast buffet was tasty, staff was always attentive, abundant wait staff, beautiful views, adults only pool, and although a resort, didn’t feel penned in.
Reviewed on Apr 24, 2026
Sundial Beach Resort & Spa
1451 Middle Gulf Drive Sanibel FL
A spa, ocean-view dining, and a garden await visiting couples at this upscale aparthotel. The property also offers a hot tub, pool cabanas, and a waterfront ...
8.6/10 Excellent! (2,633 reviews)
Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub
Travelers say...
Long wait to get checked in. Then we didn’t like the room so we paid to upgrade. Again took a long time and once we got to the room it was not clean, stains on carpets, light bulbs out, mold around showers. Not what we expected. There was a wedding going on so it was also very busy with those guests. ...
Reviewed on Apr 25, 2026
Turtle Beach Resort
9049 Midnight Pass Road Siesta Key FL
A garden, free pool cabanas, and private dining await couples visiting this romantic hotel. The property also offers a terrace, an outdoor pool, and a waterfront ...
8.8/10 Excellent! (345 reviews)
Enjoyed our quiet and comfortable stay at Turtle Beach Resort. The staff were warm, attentive, and proactive. The property is charming and secluded, at the end of a key and right on the edge of a serene bay with shared amenities like the pool, grill, kayaks, fishing gear, and hammocks. There are ...
Reviewed on Apr 23, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
