Southwest Florida Vacation Packages 2025/2026 from $477

Southwest Florida flight + hotel vacation packages

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

Casa Boutique Hotel

South Beach

$477

per person

Nov 11 - Nov 18

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 coffee shop, and dry cleaning are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,689

per person

Nov 15 - Nov 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.

Cavalier Hotel South Beach

South Beach

$539

per person

Nov 11 - Nov 18

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.

Henrosa Hotel

South Beach

Save 100% on your flight

$480

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.

President Villa

South Beach

Save 100% on your flight

$508

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free full breakfast each morning. 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

$77 nightly

$88 total

Sep 9 - Sep 10

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.

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

Free Cancellation

Reserve now, pay when you stay

$214 nightly

$238 total

Sep 9 - Sep 10

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.

Margaritaville Beach Resort Fort Myers

251 Crescent Street, Fort Myers Beach, FL

$165 nightly

$185 total

Sep 9 - Sep 10

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.

Lani Kai Beachfront Resort

1400 Estero Blvd, Fort Myers Beach, FL

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$129 total

Sep 16 - Sep 17

Total with taxes and fees

This hotel features 2 beach bars, a bar/lounge, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.

Sunseeker Resort Charlotte Harbor

5500 Sunseeker Way, 785, Punta Gorda, FL

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$196 total

Oct 2 - Oct 3

Total with taxes and fees

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this luxury 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.

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd, Marco Island, FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$204 total

Sep 15 - Sep 16

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this resort. Spend a day at the beach parasailing, or relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas.

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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

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

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

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 $477. 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.