Southwest Florida Vacations from ¥279,539

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The Latest Southwest Florida Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Boulan South Beach

Boulan South Beach

South Beach
¥279,539
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,017 reviews)
EAST Miami

EAST Miami

Brickell
¥526,712
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Miami (MIA)
9.2/10 Wonderful! (4,177 reviews)
The Penguin Hotel

The Penguin Hotel

South Beach
¥388,128
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Miami (MIA)
8.4/10 Very Good! (1,996 reviews)
Hotel is showing some aging and the breakfast at the other / sister hotel was a zoo

Reviewed on Oct 12, 2026

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

Downtown Miami
¥471,390
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Miami (MIA)
9/10 Wonderful! (2,636 reviews)
The hotel looks nice but cleaning and painting needs to be done especially on the lobby area on the way to the elevator the walls were very dirty and so was that carpet .

Reviewed on Oct 11, 2026

President Hotel

President Hotel

South Beach
¥370,274
per person
Dec 26 - Dec 31
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Miami (MIA)
8.4/10 Very Good! (2,812 reviews)
The experience was great!

Reviewed on Oct 12, 2026

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 person carrying a child on their shoulders on a bridge with a view of greenery and a clear sky.

Central Naples

If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.

A wooden pier extending into calm waters at dusk, with two illuminated structures at the end.

East Naples

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

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.

Find the Best Southwest Florida Vacation Packages

Things to do near Southwest Florida

Shopping

Coconut Point Mall, located 11.3km from Southwest Florida, offers a vibrant shopping experience with various businesses and entertainment options. For unique finds, visit the Flamingo Island Flea Market, 12.9km away, or explore Naples Marina and Excursions, just 19.3km from the area.

Recreation

Experience the energetic atmosphere at JetBlue Park at Fenway South, where you can enjoy baseball games and local sports events. For a peaceful day outdoors, head to Old Corkscrew Golf Club, surrounded by nature, or indulge in luxury at Bonita Bay East, a private club offering upscale amenities and relaxation.

Adventure

Experience thrilling water slides and wave pools at Sun N Fun Lagoon, located 19.3km from Southwest Florida. For arcade excitement, visit Beach Bowl, 24.1km away, or Bowland Midpoint, 32.2km away, where family-friendly games and adventurous vibes await.

Nightlife

Southwest Florida's nightlife is vibrant and diverse. Visit the lively bars at Fort Myers Beach for beachfront fun, or enjoy upscale cocktails at Naples’ elegant lounges. For dancing, check out clubs in downtown Fort Myers, where the energy keeps you moving all night long.

*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 lovers and families seeking outdoor adventures. With its stunning beaches, urban parks, and modern colleges, there are plenty of attractions to explore. Popular destinations include Fort Myers Beach and various other local sites that cater to those looking for a memorable family experience. Whether you're searching for the best beaches or exciting activities, Southwest Florida offers something for every traveler.

  • Florida Gulf Coast University: This modern university, located 8.0km from Southwest Florida, offers a vibrant campus atmosphere with a blend of academic excellence and city vibes. Explore its beautiful grounds and enjoy the energetic environment that fosters creativity and learning.
  • Florida Southwestern State College: Situated 22.5km from Southwest Florida, this institution features a contemporary campus that radiates city vibes. It's a great place to soak in the local culture and observe the spirited student life in action.
  • Hertz Arena: Just 8.0km away, Hertz Arena is a lively entertainment venue that hosts various events, from concerts to sports. Experience the family-friendly atmosphere and enjoy the excitement of live performances in this dynamic space.

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Southwest Florida.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Southwest Florida.
  • 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 Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
¥6,803
¥11,086 total
Oct 19 - Oct 20
includes taxes & fees
Kompose Boutique Hotel
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
¥25,519
¥36,397 total
Oct 26 - Oct 27
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
¥25,646
¥33,452 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (2,607 reviews)
"Breakfast was outstanding, clean and very friendly staff all around."

Reviewed on Oct 12, 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 47,554 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.

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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An aerial view of a city intersection with a central green space surrounded by roads and buildings.

St. Armands Circle

9.4/10 (5,556 reviews)
This elegant open-air marketplace blends upscale shopping with European charm, surrounded by historic Ringling statues. Browse over 130 boutiques and dine al fresco at sidewalk cafés overlooking Circle Park.
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A beach with a lifeguard tower, a parked car, and people relaxing under umbrellas.

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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The Mall at the University Town Center with a modern building, palm trees, and a clear sky.

Mall at University Town Center

9.0/10 (2,156 reviews)
The Mall at UTC offers a premier shopping experience with over 140 stores from luxury boutiques to popular brands. Enjoy upscale dining options in a spacious, climate-controlled environment with modern architecture.
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A beach with palm trees, a clear blue sky, and a building complex in the background.

Vanderbilt Beach

9.2/10 (2,388 reviews)
Vanderbilt Beach dazzles with powdery white sand and crystal-clear Gulf waters perfect for shell collecting. Arrive before sunset to witness the sky's dramatic transformation.
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What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

¥9,585
per adult
92% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

¥17,255
per adult
98% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
Narrated Boat Tour - Palm Beach Celebrity Homes and Local History

Narrated Boat Tour - Palm Beach Celebrity Homes and Local History

¥13,962
per adult
100% of travellers recommend
Narrated Boat Tour - Palm Beach Celebrity Homes and Local History
See all activities in Southwest Florida

Frequently asked questions

How much does a Southwest Florida vacation package cost?
Less than you might think — from just ¥279,539, in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your getaway to Southwest Florida is just a few clicks away.
How do I get a cheap travel package to Southwest Florida?
Browse and book everything in the one place with our Southwest Florida vacation packages. We have incredible bargains on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you'll have the flexibility to mix and match all you want.
Where should I stay in Southwest Florida?
You can't go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.
What are the top hotels in Southwest Florida?
Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travelers.
How far in advance should I book my Southwest Florida vacation?
Get rewarded with the widest variety at the cheapest prices by booking your vacation to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream vacation!
What does an Expedia Southwest Florida travel package include?
That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida vacation looks like, you're sure to save!
What should I know before booking a Southwest Florida travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.
If I'm not able to travel, can I cancel my Southwest Florida vacation package?
It's hard to predict what the future holds, so it's good to know that you can cancel or change your Southwest Florida vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

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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.