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.
Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was CA $2,967, price is now CA $1,650 per person
CA $1,650
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this family-friendly aparthotel in Bay Harbor Islands. Enjoy free WiFi, private pools, and a rooftop terrace. Popular attractions Aventura Mall and Miami Beach Boardwalk 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 $24,921, price is now CA $12,661 per person
CA $12,661
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this 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.
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 $3,709, price is now CA $1,970 per person
CA $1,970
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a private beach, and 3 bars/lounges. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Tideline Palm Beach Ocean Resort and Spa

Tideline Palm Beach Ocean Resort and Spa

4 out of 5
Price was CA $6,566, price is now CA $3,557 per person
CA $3,557
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Fort Lauderdale (FLL)
Book a stay at this beach hotel in Palm Beach. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Worth Beach and Worth Avenue are located nearby.
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Price was CA $4,497, price is now CA $2,499 per person
CA $2,499
per person
Feb 22 - Feb 28
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Book a stay at this luxury resort in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Little Conch Key and Walkers Island 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
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 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 $518 per night
CA $518
CA $644 total
Dec 16 - Dec 17
includes taxes & fees
Book a stay at this 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 Punta Gorda FL
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $283 total
Jan 9 - Jan 10, 2026
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
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 $223 per night
CA $223
CA $319 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this 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
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Free cancellation
Reserve now, pay when you stay
The price is CA $197 per night
CA $197
CA $251 total
Dec 17 - Dec 18
includes taxes & fees
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
Pool
Free WiFi
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 $211 per night
CA $211
CA $277 total
Dec 16 - Dec 17
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 Coquina Beach and Bean Point Beach are located nearby.
Pool
Breakfast included
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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

4.5/5(75 reviews)

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

4.5/5(46 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.

Lido Beach
St. Armands Circle showing a statue or sculpture

St. Armands Circle

4.5/5(49 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.

St. Armands Circle

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 $1,650. 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