Southwest Florida Vacations from $385

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Your Southwest Florida Vacation

Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.

The Latest Southwest Florida vacation packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
Riverside Hotel
Park Central South Beach
The Retreat Collection at 1 Hotel & Homes South Beach
President Villa
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Where to stay in Southwest Florida

Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Aug 24 to Aug 25
$87 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (4,258 reviews)
Everything was perfect. Great value.
"Everything was perfect. Great value."

Reviewed on Aug 22, 2025

Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$197 nightly
The price is $219 total per night from Sep 1 to Sep 2
$219 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,721 reviews)
"Amazing hospitality and service. Location to the beach is not the best."

Reviewed on Aug 23, 2025

Naples Grande Beach Resort
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $222 total per night from Aug 24 to Aug 25
$222 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (1,372 reviews)
Relaxing long weekend
"Another great stay. The suites are great and had plenty of room and comforts. The concierge was definitely nice to be able to access, as were the sodas and snacks. I do wish Harbor Yards wasn’t so plastic-crazy. The weekends seem to attract many younger people with day passes, so keep that in mind ..."

Reviewed on Aug 20, 2025

Sunseeker Resort Charlotte Harbor
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.

Things to do near Southwest Florida

Southwest Florida is perfect for a family vacation, offering stunning beaches and a variety of outdoor adventures. Enjoy activities like airboat tours, golfing at scenic courses, and exploring local shopping malls. Don't miss out on Restaurant Week to savor the region's culinary delights. Whether you’re seeking relaxation or excitement, Southwest Florida has something for everyone.

Shopping

Discover Coconut Point Mall, just 7 miles away, offering a vibrant mix of entertainment and shopping. Visit Flamingo Island Flea Market, 8 miles away, for unique finds and local goods. Don't miss Naples Marina and Excursions, located 12 miles away, perfect for gifts and souvenirs.

Recreation

Experience the energy at JetBlue Park at Fenway South, where you can catch a game and soak in the vibrant sports atmosphere. For outdoor relaxation, Old Corkscrew Golf Club offers beautiful views and a challenging course. Enjoy family fun at GlowGolf, a mini-golf adventure filled with excitement.

Adventure

At Sun N Fun Lagoon, enjoy thrilling water slides and a lazy river, perfect for family fun and adventure. Beach Bowl offers exciting arcade games and bowling, ensuring a lively atmosphere for all ages. Bowland Midpoint combines bowling with arcade excitement, making it a fantastic spot for family bonding.

Nightlife

Southwest Florida's nightlife buzzes with energy. Visit The Blue Martini for vibrant cocktails and live music. For dancing, check out Club A, known for its DJ sets. Don’t miss the rooftop bar at the Hotel Indigo for stunning views and relaxed vibes to end your night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Southwest Florida

Southwest Florida is perfect for beach and outdoor family vacations, featuring popular attractions like Fort Myers Beach and urban parks. With a mix of modern colleges and universities nearby, visitors can enjoy a variety of experiences tailored to outdoor enthusiasts and beach lovers alike. Explore the best beaches and local attractions to make the most of your time in this beautiful region.

  • Florida Gulf Coast University: Experience the vibrant atmosphere of this modern university, just 5 miles from Southwest Florida. With its contemporary architecture and lively campus life, you can enjoy a taste of city vibes while exploring the beautiful grounds and engaging with students and faculty.
  • Hertz Arena: Located 5 miles away, this entertainment hub offers a family-friendly environment filled with exciting events. Whether it's a concert, hockey game, or family show, Hertz Arena is a great place to create lasting memories with loved ones.
  • Barefoot Beach: Just 12 miles from Southwest Florida, this stunning beach is perfect for sunbathing, swimming, and shell collecting. With its pristine sandy shores and tranquil waves, Barefoot Beach provides a serene escape for beach lovers.

Best time to go to Southwest Florida

The best time to visit Southwest Florida can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Southwest Florida falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature around Southwest Florida falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No RainMostly SunnyAverageSlightly High
February67.1°F (19.5°C)No RainMostly SunnySlightly HighSlightly High
March70.3°F (21.3°C)No RainSunnySlightly HighSlightly High
April73.8°F (23.200000000000003°C)Light RainMostly SunnyAverageAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Moderate RainMostly SunnySlightly HighAverage
August83.5°F (28.6°C)Moderate RainMostly SunnyAverageSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnySlightly LowSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No RainMostly SunnySlightly LowAverage
December69.3°F (20.700000000000003°C)No RainMostly SunnyAverageAverage

Tips to save on your trip to Southwest Florida

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Southwest Florida during the low season (August to October) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.