Southwest Florida Vacations 2026 from CA $966

Southwest Florida flight + hotel packages

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

The W - Bayshore Unit 1003

East Fort Lauderdale

CA $966

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

Stay at this apartment in Fort Lauderdale. Enjoy free WiFi, 12 outdoor pools, and valet parking (surcharge). Popular attractions Las Olas Beach and Fort Lauderdale Beach are located nearby.

Creekside Inn

CA $1,309

per person

May 27 - Jun 2

found 11 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.

Miami Downtown Condos

Downtown Miami

CA $1,405

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

Book a stay at this luxury condo in Miami. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Popular attractions Bayside Marketplace and Kaseya Center are located nearby.

Casablanca Miami Beach

North Beach

CA $1,673

per person

Jun 19 - Jun 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

Book a stay at this beach aparthotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and laundry facilities. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.

President Hotel Villa

South Beach

CA $1,032

per person

Jul 9 - Jul 12

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.

Top Southwest Florida hotels deals

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free cancellation

CA $102

CA $115 total

May 3 - May 4

includes taxes & fees

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lido Beach and Mote Marine Laboratory & Aquarium are located nearby.

Pool

Parking included

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free cancellation

Reserve now, pay when you stay

CA $199

CA $292 total

May 22 - May 23

includes taxes & fees

Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.

Pool

Hot tub

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

Free cancellation

Reserve now, pay when you stay

CA $290

CA $398 total

May 4 - May 5

includes taxes & fees

Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions South Marco Beach and Winterberry Beach are located nearby.

Pool

Hot tub

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free cancellation

Reserve now, pay when you stay

CA $228

CA $296 total

May 4 - May 5

includes taxes & fees

Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

Pool

Breakfast included

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free cancellation

Reserve now, pay when you stay

CA $84

CA $111 total

Apr 30 - May 1

includes taxes & fees

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Mote Marine Laboratory & Aquarium are located nearby.

Pool

Hot tub

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

Free cancellation

Reserve now, pay when you stay

CA $218

CA $242 total

Apr 27 - Apr 28

includes taxes & fees

Book a stay at this family-friendly hotel in Naples. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Popular attractions Paradise Coast Sports Compex and Swamp Buggy Races are located nearby.

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.

Popular places to visit

Siesta Key Beach

Nothing says vacation like spending a lazy day at Siesta Key Beach, a popular beach in Siesta Key. Amble around this relaxing area's seaside or experience its live music.

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

Nothing says vacation like spending a lazy day at Venice Beach, a popular beach in 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 CA $966. 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.