Southwest Florida Romantic Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
- Tween Waters Island Resort & Spa
Jan 8 - Jan 10Tween Waters Island Resort & Spa + Flight
Captiva2 nights3.0 star property8.8/10 - Excellent (1,002 reviews)Roundtrip • New York (JFK) - Fort Myers (RSW)JFK - RSW • Nonstop RSW - JFK • Nonstop$596$447found 20 hours agoper traveler - voco Sarasota by IHG
Jan 31 - Feb 5voco Sarasota by IHG + Flight
Central Sarasota5 nights3.5 star property9.0/10 - Wonderful (1,002 reviews)Roundtrip • Islip (ISP) - Tampa (TPA)ISP - TPA • 1 stop TPA - ISP • 1 stop$1,038$644found 6 hours agoper traveler - LaPlaya Beach & Golf Resort - A Noble House Resort
Jan 10 - Jan 14LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach4 nights4.5 star property9.0/10 - Wonderful (1,001 reviews)"Overall, worth the stay. The place could use some updates."Reviewed November 5, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • Nonstop PGD - PSM • Nonstop - Cedar Cove Resort and Cottages
Dec 10 - Dec 15Cedar Cove Resort and Cottages + Flight
Holmes Beach5 nights3.0 star property9.4/10 - Exceptional (622 reviews)Roundtrip • New York (LGA) - Tampa (TPA)LGA - TPA • Nonstop TPA - LGA • Nonstop$1,371$886found 22 hours agoper traveler - Olde Marco Island Inn and Suites
Jan 14 - Jan 19Olde Marco Island Inn and Suites + Flight
Olde Marco5 nights3.0 star property9.0/10 - Wonderful (1,001 reviews)"This apartment like room was perfect. It had a full kitchen, dinning room amd livingroom. A bathreem in each bedroom and great food right out the door. We loved our stay."Reviewed November 8, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)PSM - PGD • Nonstop RSW - BOS • 1 stop
Discover the most popular places to visit in Southwest Florida
What to do in Southwest Florida
Palm Beach: Sightseeing Catamaran Cruise
$61
per adult
92% of travelers recommend
West Palm Beach Enjoy Sunset on a Tiki Cruise
$69
per adult
0% of travelers recommend
Your Vacation, Your Experience, Your Snorkeling at Your Pace
$110
per adult
98% of travelers recommend
Top Romantic Southwest Florida Hotels
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse21.4 mi from Southwest Florida
9.2 out of 10, Wonderful, (58 reviews)
9.2/10
Wonderful
(58 reviews)
"We loved our stay! The property is walking distance to the beach with a very nice bike path all the way there. There are also several business just around the corner - ice cream shop, breakfast, souvenir store, restaurant. We loved it. The cottage was spacious and the AC was very effective. The shower is small, but you can see that from the listing pictures. It was close to everything and we thought great value for the price. Would definitely stay again!"
$328 nightly
The price is $347
$347 total
Nov 9 - Nov 10
Total with taxes and fees
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!21.4 mi from Southwest Florida
9.6 out of 10, Exceptional, (55 reviews)
9.6/10
Exceptional
(55 reviews)
"Loved this place! So private and cute! We walked to Wickies for breakfast and lunch and did Mudbugs for dinner! Best beaches were Blind Pass and Tarpon Bay! Make sure to use the code for a discount for Adventures in Paradise Shelling tours!"
$266 nightly
The price is $283
$283 total
Nov 16 - Nov 17
Total with taxes and fees
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes26.6 mi from Southwest Florida
9.0 out of 10, Wonderful, (24 reviews)
9.0/10
Wonderful
(24 reviews)
"Enjoyed our stay. Perfect sized cottage for the two of us. Wish the bathroom had a shelf for cosmetic bags and dop kits, but we managed. Liked the beach access and parking pass even though it was a long walk from the parking lot to the beach. Communication with the owners was very was good. No dishwasher, no laundry facilities, no hair dryer but towels and beach chairs (too low for us old folks) were provided. Umbrella would have been nice. Lots of the island things to do were within...
$366 nightly
The price is $384
$384 total
Nov 15 - Nov 16
Total with taxes and fees
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!21.4 mi from Southwest Florida
9.0 out of 10, Wonderful, (77 reviews)
9.0/10
Wonderful
(77 reviews)
$272 nightly
The price is $289
$289 total
Nov 9 - Nov 10
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
Old Floridian cottage in Historic Gulf Village39.9 mi from Southwest Florida
9.8 out of 10, Exceptional, (61 reviews)
9.8/10
Exceptional
(61 reviews)
"Yes Tom was welcoming and helpful."
$231 nightly
The price is $260
$260 total
Dec 1 - Dec 2
Total with taxes and fees
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.19.6 mi from Southwest Florida
9.8 out of 10, Exceptional, (86 reviews)
9.8/10
Exceptional
(86 reviews)
"This quaint lovely cottage is exactly as described, pictured, comfortable, very clean & delightfully decorated in a Florida ranch country vibeDeer going through at dusk, the sweetest ranch dog came by to wag hi So peaceful & sereneThank you Host Beverly"
$235 nightly
The price is $255
$255 total
Nov 9 - Nov 10
Total with taxes and fees
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!26.6 mi from Southwest Florida
9.2 out of 10, Wonderful, (45 reviews)
9.2/10
Wonderful
(45 reviews)
$414 nightly
The price is $434
$434 total
Nov 10 - Nov 11
Total with taxes and fees
Lovers Key Resort Fort Myers Beach High floor Stunning Views Pool balcony
Lovers Key Resort Fort Myers Beach High floor Stunning Views Pool balcony19.8 mi from Southwest Florida
10.0 out of 10, Exceptional, (64 reviews)
10/10
Exceptional
(64 reviews)
"We have stayed at Lovers Key Resort several times and it is always amazing. This stay was no exception. Sandra's condo was very clean and well stocked with everything you could possibly need. The view from the balcony was amazing and we enjoyed watching the dolphins and manatees every evening."
$289 nightly
The price is $320
$320 total
Nov 9 - Nov 10
Total with taxes and fees
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.
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.
How 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 $447. 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?