Southwest Florida Vacation Packages 2026 from $655

Southwest Florida flight + hotel vacation packages

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

Creekside Inn

$655

per person

May 24 - May 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

Casablanca Miami Beach

North Beach

$3,725

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Pelican Hotel

South Beach

Save 100% on your flight

$715

per person

May 19 - May 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. 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. Valet parking, a business center, and limo/town car service are also offered.

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$871

per person

Jun 14 - Jun 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.

Top Southwest Florida hotels deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$226 nightly

$253 total

Apr 21 - Apr 22

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$75 nightly

$85 total

May 3 - May 4

Total with taxes and fees

This hotel features an outdoor pool and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Pool

Parking included

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$102 total

Apr 15 - Apr 16

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

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$229 total

Apr 21 - Apr 22

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

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

1538 Cape Coral Pkwy E Cape Coral FL

Free Cancellation

$105 nightly

$117 total

Apr 19 - Apr 20

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

$290 nightly

$324 total

Apr 21 - Apr 22

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

Don't see what you're looking for?

See all available properties in Southwest Florida

View all properties

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

Siesta Key Beach

4.5/5(1,449 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(1,237 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(1,257 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 $655. 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.