Southwest Florida Vacation Packages 2026/2026 from $616

Southwest Florida flight + hotel vacation packages

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

Flow Miami Hotel

Downtown Miami

$616

per person

Jan 8 - Jan 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This apartment features an outdoor pool and a 24-hour gym. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.

Hawks Cay Resort

$739

per person

Feb 11 - Feb 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

Cavalier Hotel South Beach

South Beach

$806

per person

Jan 31 - Feb 7

found 1 day 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.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$846

per person

Jan 27 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

President Hotel Villa

South Beach

$674

per person

Jan 31 - Feb 7

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.

Top Southwest Florida hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$112 total

Dec 14 - Dec 15

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.

Pool

Hot Tub

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Free Cancellation

$401 nightly

$446 total

Dec 21 - Dec 22

Total with taxes and fees

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Family-friendly amenities include a waterslide and kid-friendly dining, along with tennis lessons.

Pool

Hot Tub

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$204 total

Dec 15 - Dec 16

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.

Pool

Hot Tub

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

$212 nightly

$237 total

Dec 15 - Dec 16

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.

Pool

Spa

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$182 total

Dec 10 - Dec 11

Total with taxes and fees

This smoke-free hotel features 3 restaurants, 3 beach bars, and 6 bars/lounges. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and perks like free WiFi.

Pool

Free WiFi

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$200 total

Dec 15 - Dec 16

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.

Pool

Breakfast included

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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

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

4.5/5(1,425 reviews)

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.

Lido Beach

4.5/5(1,225 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(1,234 reviews)

You can browse for the perfect souvenirs at St. Armands Circle during your visit to Sarasota. Stroll along the beautiful beaches 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 $616. 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.