Southwest Florida Vacations 2026 from CA $1,009

Southwest Florida flight + hotel packages

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

The Penguin Hotel

South Beach

CA $1,009

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Creekside Inn

CA $1,381

per person

Jun 6 - Jun 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.

Casablanca Miami Beach

North Beach

CA $1,991

per person

Jun 12 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Book a stay at this beach aparthotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and laundry facilities. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $13,172

per person

May 12 - May 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

Book a stay at this 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.

Carillon Miami Wellness Resort

North Beach

CA $1,300

per person

Jun 15 - Jun 18

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Book a stay at this luxury hotel in Miami Beach. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Top Southwest Florida hotels deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free cancellation

Reserve now, pay when you stay

CA $261

CA $362 total

May 7 - May 8

includes taxes & fees

Book a stay at this spa 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

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free cancellation

Reserve now, pay when you stay

CA $130

CA $164 total

Apr 9 - Apr 10

includes taxes & fees

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Mote Marine Laboratory & Aquarium are located nearby.

Pool

Hot tub

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free cancellation

CA $104

CA $117 total

May 3 - May 4

includes taxes & fees

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lido Beach and Mote Marine Laboratory & Aquarium are located nearby.

Pool

Parking included

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

1538 Cape Coral Pkwy E Cape Coral FL

Free cancellation

CA $134

CA $149 total

May 4 - May 5

includes taxes & fees

Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dolphin Marina and Cape Coral Bridge are located nearby.

Pool

Breakfast included

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free cancellation

Reserve now, pay when you stay

CA $248

CA $319 total

Apr 12 - Apr 13

includes taxes & fees

Stay at this 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 Coquina Beach are located nearby.

Pool

Breakfast included

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

CA $367

CA $480 total

Apr 28 - Apr 29

includes taxes & fees

Book a stay at this 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 Crescent Beach Family Park are located nearby.

Pool

Spa

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See all available properties in Southwest Florida

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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(77 reviews)

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

Lido Beach

4.5/5(47 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.

Venice Beach

4.5/5(31 reviews)

If a restful vacation is part of your travel plans, Venice Beach might be the perfect place to seek out during your trip to Venice.

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.