Southwest Florida Vacation Packages 2026 from $480

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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.

Luxuri Suites

South Beach

$480

per person

Sep 12 - Sep 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

6.8/10 (57 reviews)

Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

Casablanca Miami Beach

North Beach

$4,160

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (327 reviews)

Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on Jul 23, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,522

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$821

per person

Sep 9 - Sep 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,113 reviews)

Omni Fort Lauderdale Hotel

East Fort Lauderdale

Save 100% on your flight

$1,272

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (516 reviews)

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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

A clear turquoise sea, a sandy beach, and a rocky outcrop with palm trees.

North Captiva

Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.

A coastal cityscape with high-rise buildings, palm trees, and a clear blue sky.

South End

While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.

A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village

Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.

A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.

South Village

While visiting South Village, you might make a stop by sights like Safe Harbor Siesta Key and Crescent Beach.

Stay near popular Southwest Florida attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 reviews)

Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favorite.

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A beach with lifeguard towers, clear turquoise water, and people sunbathing.

Lido Beach

9.4/10 (6,329 reviews)

Lido Beach enchants with pristine white sands and calm waters along Sarasota's coast. Spend the day swimming in crystal-clear waters before strolling to nearby St. Armands Circle for upscale dining.

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A beach with white sand, turquoise water, and a rocky area in the foreground. There are palm trees and a building in the background.

Naples Beach

9.4/10 (6,040 reviews)

Pristine white sands and clear Gulf waters frame the historic Naples Pier, stretching 1,000 feet into the sea. Watch for dolphins while enjoying panoramic sunset views from this quintessential Florida beach.

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A crowded beach with people swimming and walking along the shore.

Venice Beach

9.2/10 (2,687 reviews)

Known as the "Shark Tooth Capital of the World," Venice Beach offers pristine sands and clear Gulf waters. Search for fossilized treasures along the shoreline or simply relax beneath the iconic sail-style pavilion.

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A bustling street with palm trees, a yellow building, and people walking.

Fifth Avenue South

9.4/10 (2,799 reviews)

Fifth Avenue South pulses as Naples' elegant heart, lined with upscale boutiques and art galleries. Stroll beneath swaying palms and enjoy ambient lighting and outdoor dining when the avenue truly comes alive.

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What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

$61

per adult

100% of travellers recommend

West Palm Beach Private Boat Cruise and Tour with a Captain

$290

per traveler

Scenic Hakuna Matata Sunset Cruise in West Palm Beach

$66

per adult

94% of travellers recommend

See all activities in Southwest Florida

Southwest Florida Hotel Deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$65 nightly

$73 total

Aug 9 - Aug 10

Total with taxes and fees

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Fully refundableReserve now, pay when you stay

$219 nightly

$245 total

Aug 16 - Aug 17

Total with taxes and fees

9.2/10 Wonderful! (3,156 reviews)

"Excellent"

Reviewed on Aug 7, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$179 nightly

$203 total

Aug 16 - Aug 17

Total with taxes and fees

9.4/10 Exceptional! (2,445 reviews)

"We had the best two night stay here this week. We were welcomed at check in, our room was ready early and gorgeous!! The hotel as a whole was beautifully decorated and so welcoming- coffee or water on offer in reception. Games and books on offer. Complimentary breakfast- which was great. Towels for ..."

Reviewed on Aug 7, 2026

See all 47,293 properties in Southwest Florida

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	65.7°F (18.7°C)	No Rain	Mostly Sunny	Average	Slightly High
February	67.1°F (19.5°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
March	70.3°F (21.3°C)	No Rain	Sunny	Slightly High	Slightly High
April	73.8°F (23.200000000000003°C)	Light Rain	Mostly Sunny	Average	Average
May	78.8°F (26.0°C)	Light Rain	Mostly Sunny	Average	Average
June	82.2°F (27.9°C)	Light Rain	Mostly Sunny	Average	Average
July	83.1°F (28.4°C)	Moderate Rain	Mostly Sunny	Slightly High	Average
August	83.5°F (28.6°C)	Moderate Rain	Mostly Sunny	Average	Slightly Low
September	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	78.6°F (25.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	73.0°F (22.8°C)	No Rain	Mostly Sunny	Slightly Low	Average
December	69.3°F (20.700000000000003°C)	No Rain	Mostly Sunny	Average	Average

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.