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 $873

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (1,747 reviews)

Very comfortable bed and bedding. Quick overnight stay before flight home.

Reviewed on Aug 10, 2026

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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 $980

per person

Nov 5 - Nov 8

found 13 hours ago

Roundtrip non-stop flight included

Syracuse (SYR) to Tampa (TPA)

8.8/10 Excellent! (1,747 reviews)

Very comfortable bed and bedding. Quick overnight stay before flight home.

Reviewed on Aug 10, 2026

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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 $658

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8.6/10 Excellent! (2,645 reviews)

DoubleTree by Hilton Sarasota Bradenton Airport

CA $873

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (1,747 reviews)

Very comfortable bed and bedding. Quick overnight stay before flight home.

Reviewed on Aug 10, 2026

Quality Inn Fort Myers Cape Coral

CA $1,221

per person

Sep 11 - Sep 15

found 1 day ago

Roundtrip flight included

Abbotsford (YXX) to Fort Myers (RSW)

7.6/10 Good! (390 reviews)

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Cheap Hotels in Southwest Florida

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 ...

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 ...

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 47,330 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.