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.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was CA $2,771, price is now CA $1,357 per person
CA $1,357
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy free WiFi, a private beach, and 3 bars/lounges. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was CA $6,029, price is now CA $2,735 per person
CA $2,735
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and a rooftop terrace. 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
Price was CA $18,886, price is now CA $8,710 per person
CA $8,710
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $5,004, price is now CA $2,402 per person
CA $2,402
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 4-star historic resort in Miami Beach. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
Maison Felix

Maison Felix

2 out of 5
North Beach
Price was CA $6,018, price is now CA $3,029 per person
CA $3,029
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy a 24-hour front desk, daily housekeeping, and a garden. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area 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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Free cancellation
The price is CA $281 per night
CA $281
CA $382 total
Nov 25 - Nov 26
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 Naples Zoo at Caribbean Gardens are located nearby.
Pool
Hot tub
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $196 per night
CA $196
CA $281 total
Oct 29 - Oct 30
includes taxes & fees
Stay at this 4-star 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.
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is CA $211 per night
CA $211
CA $306 total
Oct 31 - Nov 1
includes taxes & fees
Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
Pool
Spa
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $167 total
Nov 5 - Nov 6
includes taxes & fees
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
11800 Coconut Cove Drive, Bonita Springs, FL
Free cancellation
The price is CA $175 per night
CA $175
CA $250 total
Nov 11 - Nov 12
includes taxes & fees
Stay at this 4-star golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
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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

If a restful vacation is part of your travel plans, Venice Beach might be the perfect place to seek out during your trip to 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 $1,357. 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