Southwest Florida Vacation Packages 2026 from $535

Southwest Florida flight + hotel vacation packages

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

District 225 - Rooftop Pool - Gym - Parking - Downtown Miami

Downtown Miami

Save 100% on your flight

$535

per person

Jan 18 - Jan 22

found 22 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

A full-service spa, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free apartment. Business travelers can take advantage of the free WiFi in public areas. Free parking, a communal living room, and express check-out are also offered.

Avi Lux Stay

East Fort Lauderdale

$751

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free aparthotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and luggage storage are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,531

per person

Dec 7 - Dec 11

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.

Broadway Suites Downtown by RocketStay

Coral Way

Save 100% on your flight

$808

per person

Jan 3 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This apartment features a terrace, laundry facilities, and free self parking. Business travelers can take advantage of the express check-in. A garden and express check-out are also provided.

1 Hotel South Beach

South Beach

$3,001

per person

Jan 17 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.

Top Southwest Florida hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$79 total

Oct 28 - Oct 29

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

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

$210 nightly

$234 total

Oct 27 - Oct 28

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

$171 nightly

$194 total

Nov 4 - Nov 5

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

Compass by Margaritaville Hotel Naples

4805 Tamiami Trl N Naples FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$151 total

Oct 29 - Oct 30

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

Hyatt Vacation Club at Coconut Cove, Bonita Springs

11800 Coconut Cove Drive Bonita Springs FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$189 total

Oct 28 - Oct 29

Total with taxes and fees

3 outdoor pools, a lazy river, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Pool

Hot Tub

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$184 total

Nov 3 - Nov 4

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

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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.

See properties

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 $535. 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.