Southwest Florida Vacation Packages 2026 from $751

Southwest Florida flight + hotel vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$751

per person

Jan 12 - Jan 17

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 Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,023

per person

Jan 28 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel 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.

501 First Studio Balcony by Palermo Home

Downtown Miami

$769

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool is featured at this apartment, along with valet parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Henrosa Hotel

South Beach

$769

per person

Jan 9 - Jan 16

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.

The Club - Pool - Gym - Parking - Heart of Brickell

Brickell

$880

per person

Feb 2 - Feb 7

found 22 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

This apartment's 2 outdoor pools and 24-hour gym are among the featured amenities. Free self parking and luggage storage are also offered on site.

Top Southwest Florida hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$78 total

Dec 8 - Dec 9

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, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$237 total

Nov 29 - Nov 30

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 4 bars/lounges and beach bar for drinks.

Pool

Spa

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$191 total

Nov 22 - Nov 23

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

The Westin Sarasota

100 Marina View Drive Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$261 total

Nov 22 - Nov 23

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Pool

Spa

Compass by Margaritaville Hotel Naples

4805 Tamiami Trl N Naples FL

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$162 total

Nov 22 - Nov 23

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$233 total

Nov 29 - Nov 30

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

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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.

Stay near popular Southwest Florida attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 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.

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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 $751. 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.