Southwest Florida Vacations from $324

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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

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Creekside Inn
Avi Lux Stay
The Retreat Collection at 1 Hotel & Homes South Beach
President Hotel Villa
Hotel AKA West Palm
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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

Stay near popular Southwest Florida attractions

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
$87 nightly
The price is $99 total per night from Nov 1 to Nov 2
$99 total
Nov 1 - Nov 2
Total with taxes and fees
Kompose Boutique Hotel
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $234 total per night from Nov 1 to Nov 2
$234 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (2,715 reviews)
"The rooms were clean. The lobby smelled amazing. The food at chill restaurant Margaritaville was great! Staff was helpful and friendly. Overall hotel was really beautiful."

Reviewed on Oct 29, 2026

Margaritaville Beach Resort Fort Myers
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $195 total per night from Nov 29 to Nov 30
$195 total
Nov 29 - Nov 30
Total with taxes and fees
9.4/10 Exceptional! (2,632 reviews)
"Our room was very clean and modern. The front desk, bartender and each employee we encountered were polite, friendly and helpful. Breakfast was very good. We loved the bar area and took our drinks outside to sit in the patio area. We will definitely be back. The hotels’ location to Anna Maria beaches ..."

Reviewed on Oct 28, 2026

Compass Hotel by Margaritaville Anna Maria Sound
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.

Find the Best Southwest Florida Vacation Packages

Things to do near Southwest Florida

Southwest Florida offers a perfect blend of beach relaxation and outdoor adventures for family vacations. Visitors can enjoy activities like airboat tours, exploring nature, and participating in local events such as restaurant week. Don't miss out on shopping at the local mall centers and hitting the golf courses for a fun-filled experience. Whether you're seeking relaxation or adventure, Southwest Florida has something for everyone.

Shopping

Experience shopping in Southwest Florida at Coconut Point Mall, just 7 miles away, offering entertainment and family vibes. For unique finds, visit the Flamingo Island Flea Market, 8 miles away, featuring local vendors. Don't miss Naples Marina and Excursions, 12 miles away, for gifts and souvenirs.

Recreation

Experience the vibrant atmosphere at JetBlue Park at Fenway South, where you can enjoy sports events and activities. For a relaxing day outdoors, play a round of golf at Old Corkscrew Golf Club, or have fun with family at GlowGolf's mini-golf course, perfect for all ages.

Adventure

Experience thrilling fun at Beach Bowl, an exciting arcadeAdventureZone located 15 miles from Southwest Florida, offering family-friendly adventures. For splashes and water slides, visit Sun N Fun Lagoon, a vibrant waterpark 12 miles away. Don’t miss Bowland Midpoint, another fantastic arcadeAdventureZone 20 miles from the area.

Nightlife

In Southwest Florida, experience vibrant nightlife in Fort Myers and Naples, where lively bars and clubs line the streets. Visit the renowned Times Square in Fort Myers Beach for beachfront fun or explore Naples' chic lounges and live music venues for a sophisticated evening out.

*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 a perfect destination for beach lovers and families seeking outdoor adventures. With highlights like Fort Myers Beach, the area offers stunning beaches and vibrant urban parks, making it ideal for a memorable family vacation. Explore a variety of attractions that cater to outdoor enthusiasts and beachgoers alike, ensuring a delightful experience in this beautiful region of the Sunshine State.

  • Florida Gulf Coast University: Experience the vibrant atmosphere of Florida Gulf Coast University, a modern institution located 5 miles from Southwest Florida. The campus combines beautiful architecture with city vibes, offering visitors a glimpse into student life and educational innovation.
  • Hertz Arena: Located 5 miles away, Hertz Arena is the go-to destination for family entertainment. This arena hosts a variety of events, from sports to concerts, ensuring a fun-filled experience for all ages in a lively environment.
  • Barefoot Beach: Just 12 miles from Southwest Florida, Barefoot Beach is a serene escape with stunning views and soft sands. Enjoy sunbathing, beachcombing, and the soothing sounds of the waves, perfect for relaxation and outdoor activities.

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.

Southwest Florida Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tampa Intl. Airport (TPA)

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Frequently asked questions

How do vacation package prices compare across popular destinations in Southwest Florida?
For a week-long Southwest Florida vacation package, Fort Myers typically has the lowest prices, while Marco Island tends to be the highest. A week-long trip typically costs around $950 per adult in Fort Myers, around $1,000 in Sarasota, around $1,200 in Fort Myers Beach, around $1,300 in Naples, and around $1,600 in Marco Island.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Southwest Florida vacation package?
When you bundle, you can save up to 30%*. To save money on a Southwest Florida package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Southwest Florida vacation package?
A Southwest Florida vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like Sarasota, Fort Myers, or Naples.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
Which destinations in Southwest Florida offer the best-value vacation package deals?
Fort Myers, Sarasota, Cape Coral, Naples, and Fort Myers Beach are some of the top destinations for cheap Southwest Florida vacation package deals. For an affordable weekend getaway, Fort Myers is often among the most budget-friendly options, with package prices starting around $400 per adult. For notable bundle savings, Fort Myers is also among the best options, with flight-and-hotel bundles saving around $210 per adult for a two-week trip.

Browse cheap vacation packages in Southwest Florida on Expedia to compare current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
When is the best time to visit the top destinations in Southwest Florida?
The best time for a Southwest Florida vacation package depends on which destination you choose, as peak seasons and events can vary slightly across the region.

Naples is busiest in March and December. In March, average temperatures are around 70°F with highs of 77°F, and you can experience the Collier Fair. December sees average temperatures of 69°F with highs of 75°F. If you'd prefer fewer crowds, September is quieter, with average temperatures around 82°F and highs of 88°F.

Siesta Key sees its highest demand in July and March. July has average temperatures around 83°F with highs of 87°F, while March offers average temperatures of 68°F with highs of 74°F. For a quieter trip, January is a good option, with average temperatures around 63°F and highs of 68°F.

Fort Myers Beach is most popular in March and April. March has average temperatures around 70°F with highs of 76°F, and April sees average temperatures of 75°F with highs of 80°F. If you prefer fewer visitors, September is quieter, with average temperatures around 82°F and highs of 87°F.

Fort Myers is busiest in March and February. In March, average temperatures are around 66°F with highs of 79°F. February, with average temperatures around 67°F and highs of 75°F, also hosts events like the Edison Festival of Lights and Artfest Fort Myers. For fewer crowds, August is quieter, with average temperatures around 83°F and highs of 88°F.
What package types are available across the top destinations in Southwest Florida?
Southwest Florida offers a diverse range of vacation package types across its popular destinations like Sarasota, Naples, Fort Myers, Fort Myers Beach, and Marco Island:
  • Family: In Sarasota, the Kompose Boutique Hotel, rated 8.7 out of 10 by travelers, features family rooms and a hot tub, with travelers frequently praising its delicious food.
  • Couples: Naples offers options like the 4-star Inn on Fifth, rated 8.9 out of 10 by travelers, which provides a spa and hot tub, and travelers often highlight its spacious rooms.
  • Budget: In Fort Myers, the Comfort Inn & Suites Fort Myers Airport, rated 8.2 out of 10 by travelers, includes free breakfast and an indoor pool, with travelers frequently mentioning the spacious rooms.
  • Beach: Marco Island features the 4-star Hilton Marco Island Beach Resort and Spa, rated 8.5 out of 10 by travelers, which offers a hot tub and kitchen, and travelers often praise its beautiful location.
  • Pet-friendly: Fort Myers Beach has options like The Lighthouse Resort Inn & Suites, rated 8.2 out of 10 by travelers, providing a kitchen and outdoor pool, with travelers frequently praising the super clean rooms.
Which destinations should I consider for a Southwest Florida vacation?
When planning a Southwest Florida vacation, your ideal destination depends on your travel style and what you're looking for in a package:
  • For couples or families seeking a mix of upscale beaches and city amenities: Naples offers a blend of outdoor activities, family-friendly attractions, and urban experiences, with packages often catering to couples and those seeking a luxurious stay.
  • For beach-focused family trips: Siesta Key is known for its stunning beaches and outdoor activities, making it a strong choice for families and couples looking for a relaxing beach getaway.
  • For a tranquil island escape: Marco Island provides a primarily beach-oriented experience with plenty of outdoor activities, popular for both couples and families seeking a serene setting.
  • For lively beach fun and value: Fort Myers Beach is a popular package base, offering abundant beach activities and family-friendly options, often with budget-friendly choices.
Is Southwest Florida better suited for a beach vacation or a cultural trip?
Southwest Florida is primarily a beach and outdoor destination, making it an excellent choice for a beach vacation. Its coastline is renowned for its beautiful sandy shores, such as Naples Beach, Marco Beach, and Barefoot Beach, offering ample opportunities for sunbathing, swimming, and water sports.

While beaches are a major draw, the region also offers city and urban attractions. Destinations like Naples feature areas such as Fifth Avenue South for shopping and dining, and you can find cultural sites like the Holocaust Museum of Southwest Florida. A Southwest Florida vacation package can easily be tailored to combine relaxing beach days with engaging city experiences.
Which airports serve the main destinations in Southwest Florida?
For a Southwest Florida vacation, the primary gateway is Southwest Florida International Airport (RSW) in Fort Myers, which offers convenient access to many popular destinations in the region. Travelers can also consider flying into Tampa International Airport (TPA) to the north, or Miami International Airport (MIA) to the southeast, both of which are larger hubs that provide additional flight options and serve as good starting points for a scenic drive to Southwest Florida.
What are the top things to do across the destinations in Southwest Florida?
A Southwest Florida vacation offers a variety of activities across its many destinations, from relaxing on pristine beaches to exploring local attractions:

Browse and book things to do in Southwest Florida on Expedia.
Are there family vacation packages in Southwest Florida with kid-friendly amenities?
Yes, Southwest Florida offers a variety of family vacation packages with kid-friendly amenities across its destinations:
  • In Naples, the 4-star Naples Bay Resort & Marina, rated 8.9 out of 10 by travelers, provides family rooms and a hot tub, with travelers often praising its amazing pool.
  • Fort Myers Beach features the 3.5-star Lani Kai Beachfront Resort, rated 8.2 out of 10 by travelers, which includes family rooms and a game room, and travelers frequently highlight its beautiful facilities.
  • In Siesta Key, The Capri at Siesta, rated 9.2 out of 10 by travelers, offers family rooms and a kitchenette, with travelers often praising its perfect overall experience.
  • Fort Myers has options like Stay Well Inn & Suites, which includes family rooms and an indoor pool, and travelers frequently praise the spacious rooms.
What luxury vacation packages are available in Southwest Florida?
Southwest Florida offers a selection of luxury vacation packages, featuring high-end resorts in its most sought-after destinations:

Most Southwest Florida vacation packages pair the hotel with flights. Browse luxury vacation packages in Southwest Florida on Expedia to compare options.
When should I book vacation packages for the top destinations in Southwest Florida?
Booking times for a Southwest Florida vacation package vary by destination, with most travelers booking around 3 to 7 weeks before departure.

Travelers tend to book trips to these destinations most often from February to May, and in July. If you're planning a spontaneous getaway, Expedia also offers last-minute Southwest Florida vacation packages.
How many days do you need for a Southwest Florida vacation?
Most Southwest Florida vacation packages last around 4 days, but the ideal trip length depends on where you're going and what you'd like to experience.

Sarasota, known for its beaches and family-friendly attractions, is well-suited for a trip of around 4 days, with week-long stays being the most popular choice, allowing time to enjoy Siesta Key Beach.

Fort Myers, also a beach destination with family-friendly activities, typically sees trips of around 4 days, where weekend and week-long stays are both popular, giving you time to visit places like JetBlue Park at Fenway South.

Naples, a popular beach destination with outdoor activities, is often visited for around 4 days, with most travelers opting for week-long trips to explore its beautiful coastline, including Naples Beach.
Can I change or cancel my Southwest Florida vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Southwest Florida vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Southwest Florida vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Southwest Florida vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Southwest Florida?
To find last-minute vacation packages to Southwest Florida, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Southwest Florida vacation packages?
Free cancellation on a Southwest Florida vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Southwest Florida vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Southwest Florida getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Southwest Florida vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.