Southwest Florida Vacations 2025 from CA $864

Southwest Florida flight + hotel packages

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

Sunrise in Miami Suites

South Beach

Save 100% on your flight

per person

Jun. 22 - Jun. 27

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Miami (MIA)

Stay at this hotel in Miami Beach. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Jun. 12 - Jun. 17

found 1 day 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 Miami Beach Boardwalk are located nearby.

Ocean Club Treasure Island Hotel

per person

May 25 - May 31

found 14 hours ago

Roundtrip flight included

Toronto (YYZ) 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.

The Landon Bay Harbor - Miami Beach

Save 100% on your flight

per person

Jun. 24 - Jul. 1

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

Stay at this 3.5-star business-friendly hotel in Bay Harbor Islands. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Miami Beach Boardwalk and Aventura Mall are located nearby.

Hawks Cay Resort

Save 100% on your flight

per person

Jun. 21 - Jun. 28

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.

Top Southwest Florida hotels deals

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

CA $490

CA $600 total

includes taxes & fees

May 4 - May 5

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

Lani Kai Beachfront Resort

1400 Estero Blvd, Fort Myers Beach, FL

Free cancellation

Reserve now, pay when you stay

CA $217

CA $286 total

includes taxes & fees

Apr 21 - Apr 22

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.

Margaritaville Beach Resort Fort Myers

251 Crescent Street, Fort Myers Beach, FL

CA $412

CA $515 total

includes taxes & fees

Apr 27 - Apr 28

Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Times Square are located nearby.

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free cancellation

Reserve now, pay when you stay

CA $266

CA $332 total

includes taxes & fees

Apr 21 - Apr 22

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.

Sunseeker Resort Charlotte Harbor

5500 Sunseeker Way, 785, Punta Gorda, FL

Free cancellation

Reserve now, pay when you stay

CA $341

CA $444 total

includes taxes & fees

Apr 20 - Apr 21

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

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free cancellation

Reserve now, pay when you stay

Get rates

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 Bradenton Beach and Cortez Beach are located nearby.

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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 $864. 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.