Southwest Florida Vacation Packages

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Your Southwest Florida Vacation

Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.

Top Southwest Florida Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Deerfield Beach Resort & Spa

Embassy Suites by Hilton Deerfield Beach Resort & Spa

3.5 out of 5
Price was CA $1,488, price is now CA $828 per person
CA $828
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (1,043 reviews)
Excelente en todo para volver siempre

Reviewed on Sep. 1, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $2,346, price is now CA $1,081 per person
CA $1,081
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,211 reviews)
Clean, great staff and dining. Super friendly crew

Reviewed on Sep. 2, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $2,389, price is now CA $1,145 per person
CA $1,145
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (946 reviews)
The only thing I liked about this hotel is the food was delicious.

Reviewed on Sep. 3, 2025

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 $22,154, price is now CA $10,969 per person
CA $10,969
per person
Nov 13 - Nov 16
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $8,130, price is now CA $4,428 per person
CA $4,428
per person
Oct 15 - Oct 22
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,278 reviews)
Everything was excellent

Reviewed on Sep. 2, 2025

Where to stay in Southwest Florida

Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida
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North Captiva

Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.

Find hotels in North Captiva

Ready to book your vacation to Southwest Florida?

 

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Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $65 per night from Sep 7 to Sep 8
CA $65
CA $89 total
Sep 7 - Sep 8
includes taxes & fees
Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is CA $225 per night from Sep 10 to Sep 11
CA $225
CA $319 total
Sep 10 - Sep 11
includes taxes & fees
Naples Grande Beach Resort
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 $180 per night from Sep 9 to Sep 10
CA $180
CA $255 total
Sep 9 - Sep 10
includes taxes & fees
Margaritaville Beach Resort Fort Myers
See all 43,868 properties in Southwest Florida
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

Siesta Key Beach

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.

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

What to do in Southwest Florida

Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

CA $70
per adult
92% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

CA $151
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
snorkeling

Experience Peanut Island Adventures

CA $69
per adult
Experience Peanut Island Adventures
See all activities in Southwest Florida

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.