Southwest Florida Vacations 2025 from CA $1,009

Southwest Florida flight + hotel packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Jul 18 - Jul 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Stay at this 3.5-star beach hotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Aug 22 - Aug 27

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Ocean Club Treasure Island Hotel

per person

Jul 19 - Jul 26

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

Stay at this 4-star beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Barsala At The Wayland Condos

Save 100% on your flight

per person

Aug 9 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star aparthotel in St. Petersburg. Enjoy free WiFi, a fitness center, and in-room washers/dryers. Popular attractions Tropicana Field and Salvador Dali Museum are located nearby.

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

Save 100% on your flight

per person

Aug 24 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Miami (MIA)

Stay at this 4-star luxury hotel in Fort Lauderdale. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.

Top Southwest Florida hotels deals

Lani Kai Beachfront Resort

1400 Estero Blvd, Fort Myers Beach, FL

Free cancellation

Reserve now, pay when you stay

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Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Times Square are located nearby.

Pool

Free WiFi

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

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Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Naples Zoo at Caribbean Gardens are located nearby.

Pool

Hot tub

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free cancellation

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Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Cortez Beach and Coquina Beach are located nearby.

Pool

Breakfast included

Sunseeker Resort Charlotte Harbor

5500 Sunseeker Way, 785, Punta Gorda, FL

Free cancellation

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Stay at this 4.5-star luxury resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.

Pool

Hot tub

Margaritaville Beach Resort Fort Myers

251 Crescent Street, Fort Myers Beach, FL

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Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Times Square are located nearby.

Pool

Spa

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free cancellation

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Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Pool

Kitchen

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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.

Popular places to visit

Siesta Key Beach

4.5/5(75 reviews)

Nothing says vacation like spending a lazy day at Siesta Key Beach, a popular beach in Siesta Key. Amble around this quaint area's seaside or experience its live music.

Lido Beach

4.5/5(46 reviews)

Nothing says vacation like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.

St. Armands Circle

4.5/5(49 reviews)

When you visit St. Armands Circle, a favorite shopping spot in Sarasota, you can find the perfect gifts to bring home. Stroll along the seaside or discover the area's beautiful sunsets.

Frequently asked questions

How much are vacation packages to Southwest Florida?

Vacation packages, which include hotels and flights in Southwest Florida, start from as little as CA $1,009. Turn your travel dreams into reality and secure your trip with Travelocity today.

Where can I get the best vacation package deals for Southwest Florida?

For the best Southwest Florida package deal, turn to Travelocity. Pick from as many as 400 airlines and 1,000,000 properties around the world to create your ultimate adventure — it couldn’t be simpler.

Why should I purchase my Southwest Florida vacation bundle via Travelocity?

The three S’s — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you’ll always get the best deal available.

Can I save on my Southwest Florida car rental if I combine it with a hotel or flight?

Absolutely. And our Southwest Florida vacation packages are the ideal way to do it. With only a few clicks you can save cash as well as time by combining your bookings. Pick up the keys to your rental car and do your vacation your way. Looking for things to do? Throw some tours or experiences into your package and save on those too.

Which airport is best for Southwest Florida?

Southwest Florida is serviced by two main hubs — Southwest Florida Intl. Airport (RSW) and Naples Municipal Airport (APF).

What is there to do in Southwest Florida?

Southwest Florida boasts hidden gems around every corner, but be sure you plan a visit to both Salvador Dali Museum and Raymond James Stadium during your stay. These two attractions are popular with visitors.