Southwest Florida Vacation Packages 2026 from $429

Southwest Florida flight + hotel vacation packages

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

The Penguin Hotel

South Beach

$429

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, a terrace, and a garden are also offered.

Cavalier Hotel South Beach

South Beach

$533

per person

Apr 25 - Apr 30

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

President Hotel

South Beach

$456

per person

Apr 25 - Apr 30

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features an outdoor pool and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and a garden are also offered.

President Hotel Villa

South Beach

$456

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and luggage storage are also offered.

Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$435

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.

Top Southwest Florida hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$197 nightly

$223 total

Feb 15 - Feb 16

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$110 nightly

$125 total

Feb 17 - Feb 18

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$245 total

Mar 10 - Mar 11

Total with taxes and fees

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

$384 nightly

$429 total

Feb 16 - Feb 17

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 4 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, beach bar, and concierge services.

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$258 nightly

$292 total

Feb 16 - Feb 17

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking. Free WiFi in public areas, a snack bar/deli, and a communal living room are also on offer.

Sanibel Island Beach Resort

1231 Middle Gulf Dr Sanibel FL

Free Cancellation

Reserve now, pay when you stay

$452 nightly

$502 total

Mar 5 - Mar 6

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy perks like free self parking.

Don't see what you're looking for?

See all available properties in Southwest Florida

View all properties

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

Lido Beach

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.

Siesta Key Public Beach showing a sandy beach

Siesta Key Beach

The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

Mall at University Town Center

You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.

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 $429. 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.