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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 $1,271

per person

Jun 14 - Jun 18

found 7 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

8.8/10 Excellent! (1,569 reviews)

We love the hotel super clean and comfortable

Reviewed on Mar 23, 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 $989

per person

Apr 30 - May 3

just found

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

8.8/10 Excellent! (1,569 reviews)

We love the hotel super clean and comfortable

Reviewed on Mar 23, 2026

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4 Night Cheap holidays in Southwest Florida

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

Quality Inn Fort Myers Cape Coral

CA $567

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Fort Myers (RSW)

7.4/10 Good! (240 reviews)

The room smelled from cat urine and the tile floor was sticky

Reviewed on Mar 22, 2026

Holiday Inn Fort Myers - Downtown Area by IHG

Midtown

CA $718

per person

Apr 23 - Apr 27

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Fort Myers (RSW)

7.6/10 Good! (1,005 reviews)

Fabulous desk reception. The entire place is under reconstruction. We had a great room but had to listen to the construction noise the whole time. Service at breakfast was super also.

Reviewed on Mar 18, 2026

Fairways Inn of Naples

Palm River Estates

CA $576

per person

Jun 1 - Jun 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9.4/10 Exceptional! (1,227 reviews)

The host was friendly and very accommodating. We came in late and called ahead of time. The room was clean and comfortable.

Reviewed on Mar 19, 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! (2,375 reviews)

The pool was great, the staff was lovely, the floors were slightly dirty

Reviewed on Mar 23, 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! (5,173 reviews)

Nice hotel near airport. Clean, friendly. Enjoyed the heated pool & hot tub very much. Breakfast also very good.

Reviewed on Mar 24, 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! (1,127 reviews)

The rooms were a bit dated. Great staff, not so great breakfast

Reviewed on Mar 23, 2026

See all 46,913 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.