Southwest Florida Vacation Packages 2025 from $194

Southwest Florida flight + hotel vacation packages

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

Broadmore Miami Beach

North Beach

Save 100% on your flight

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. A coffee shop, a terrace, and luggage storage are also on offer.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Sep 6 - Sep 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. Valet parking, a terrace, and express check-out are also offered.

Miami accommodations BeachFront

South Beach

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel includes a communal living room and a virtual front desk.

Ocean Club Treasure Island Hotel

per person

Jul 18 - Jul 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Henrosa Hotel

South Beach

Save 100% on your flight

per person

Aug 5 - Aug 10

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.

Top Southwest Florida hotels deals

Lani Kai Beachfront Resort

1400 Estero Blvd, Fort Myers Beach, FL

Free Cancellation

Reserve now, pay when you stay

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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.

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

Free Cancellation

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A full-service spa, 3 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 kayaking.

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free Cancellation

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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.

Sunseeker Resort Charlotte Harbor

5500 Sunseeker Way, 785, Punta Gorda, FL

Free Cancellation

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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.

Hyatt House Naples/5th Avenue

1345 5th Avenue South, Naples, FL

Free Cancellation

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A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the outdoor pool and free buffet breakfast each morning.

Pool

Hot Tub

Margaritaville Beach Resort Fort Myers

251 Crescent Street, Fort Myers Beach, FL

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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

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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)

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 $194. 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.