Book Exclusive Southwest Florida Vacation Packages

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Southwest Florida flight + hotel packages

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

Pelican Hotel

4 out of 5
South Beach
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 3.5-star beach hotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Stay at this 3-star apartment in Miami Beach. Enjoy free WiFi, a 24-hour fitness center, and an in-room coffeemaker. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 3.5-star apartment in Miami. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions Kaseya Center and Bayside Marketplace are located nearby.

Top Southwest Florida hotels deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
Pool
Hot tub
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Free cancellation
The price is CA $194 per night
CA $194
CA $276 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Fifth Avenue South are located nearby.
Pool
Hot tub
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $208 per night
CA $208
CA $293 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this 4.5-star luxury 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
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
202 North Tamiami Trail, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $196 per night
CA $196
CA $260 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
Pool
Breakfast included
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $231 per night
CA $231
CA $294 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Coquina Beach and Anna Maria Beach are located nearby.
Pool
Breakfast included
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $174 per night
CA $174
CA $193 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. Popular attractions Fifth Avenue South and Naples Pier 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

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.

Siesta Key Beach
Lido Beach

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.

Lido Beach
Venice Beach

Venice Beach

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

Venice Beach

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 $390. 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.

Photos of local treasures

Browse Southwest Florida vacation photos for more inspiration

Fort Myers Beach which includes a beach as well as a large group of people
Burroughs Home showing a house and a garden
Delnor-Wiggins Pass State Park featuring a sandy beach as well as a couple
Naples which includes shopping and signage
Fort Myers which includes heritage architecture