Cheap Vacations in Southwest Florida 2026

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Flight and Cheap hotel deals in Southwest Florida

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

DoubleTree by Hilton Sarasota Bradenton Airport

CA $1,110

per person

Nov 30 - Dec 4

found 1 day ago

Roundtrip flight included

Saskatoon (YXE) to Tampa (TPA)

8.8/10 Excellent! (1,788 reviews)

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3 Night Cheap holidays in Southwest Florida

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

DoubleTree by Hilton Sarasota Bradenton Airport

CA $734

per person

Oct 31 - Nov 3

found 10 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (1,788 reviews)

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4 Night Cheap holidays in Southwest Florida

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

Golden Host Resort - Sarasota

North Trail

CA $543

per person

Nov 20 - Nov 24

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

8.6/10 Excellent! (2,675 reviews)

Amazing staff! Very helpful all around amazing stay

Reviewed on Sep 28, 2026

Quality Inn Fort Myers Cape Coral

CA $677

per person

Nov 1 - Nov 5

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

7.6/10 Good! (431 reviews)

AC didn't stay on long enough

Reviewed on Sep 28, 2026

Americas Best Value Inn Ft. Myers

CA $704

per person

Nov 1 - Nov 5

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

7.6/10 Good! (1,241 reviews)

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Cheap Hotels in Southwest Florida

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

20 min drive from Siesta Key Beach

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 ...

9.2/10 Wonderful! (6,072 reviews)

"The set up of the room is unusual would have preferred an actual bathroom instead of a toilet closest and a shower closet the sunk was right beside the one bed. There are 2 elevators but only one running so was squished in the elevator once with two massive towel bins. The light in our shower wasn't ..."

Reviewed on Sep 28, 2026

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

18 min drive from Siesta Key Beach

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 ...

8.6/10 Excellent! (2,686 reviews)

"Amazing staff! Very helpful all around amazing stay"

Reviewed on Sep 28, 2026

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL

17 min drive from Siesta Key Beach

Stay at this hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular ...

See all 47,615 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.