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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 $818

per person

Jul 23 - Jul 28

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (1,610 reviews)

I would like to see breakfast inckuded with our stay.

Reviewed on May 11, 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 $1,080

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Tampa (TPA)

8.8/10 Excellent! (1,610 reviews)

I would like to see breakfast inckuded with our stay.

Reviewed on May 11, 2026

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4 Night Cheap holidays in Southwest Florida

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

Fairways Inn of Naples

Palm River Estates

CA $651

per person

Jun 16 - Jun 20

found 22 hours ago

Roundtrip non-stop flight included

Detroit (DTT) to Fort Myers (RSW)

9.4/10 Exceptional! (1,296 reviews)

Everything was perfect except for the few hours they disconnected the power the day after we arrived and it was a bit uncomfortable with the heat. It took a FPL almost 5 hours to get there. Besides that, everything else was great!

Reviewed on May 10, 2026

Baymont by Wyndham Fort Myers Central

CA $825

per person

Jul 3 - Jul 7

found 8 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Fort Myers (RSW)

6.8/10 (1,056 reviews)

Shower hot water and pressure were awesome. The pool was inviting. I didn’t see any roaches in my room!

Reviewed on May 11, 2026

Naples Park Central Hotel

Old Naples

CA $757

per person

Jun 16 - Jun 20

found 22 hours ago

Roundtrip non-stop flight included

Detroit (DTT) to Fort Myers (RSW)

9.2/10 Wonderful! (1,006 reviews)

Continue to stay at this property since it’s so good

Reviewed on May 5, 2026

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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 ...

8.4/10 Very Good! (2,478 reviews)

Many of us stayed for my sisters wedding and were blocked together. The desk staff was very kind and accommodating when I asked to switch rooms to be near my sisters. My room had bottle caps behind the door and I didn’t have pillows for the second bed didn’t have pillowcases and I was only given ...

Reviewed on May 11, 2026

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! (5,344 reviews)

Great

Reviewed on May 12, 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 ...

8.8/10 Excellent! (1,148 reviews)

AC wasn't keeping up with the heat from outside and it was only 85°F outside. Instead of moving us to a different room, we were offered a fan for the room.

Reviewed on May 11, 2026

See all 47,015 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.