Pet-friendly Vacations in Southwest Florida 2026

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Flight and Pet-friendly hotel deals in Southwest Florida

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

Compass by Margaritaville Hotel Naples

Central Naples

CA $1,234

per person

Sep 18 - Sep 20

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Fort Myers (RSW)

9.6/10 Exceptional! (1,696 reviews)

Great ATMOSPHERE

Reviewed on Aug 14, 2026

The Westin Cape Coral Resort At Marina Village

Pelican

CA $1,314

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Kalispell (FCA) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Hyatt Regency Coconut Point Resort & Spa

CA $2,557

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

The staff

Reviewed on Aug 14, 2026

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3 Night Pet-friendly holidays in Southwest Florida

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

Compass by Margaritaville Hotel Naples

Central Naples

CA $796

per person

Oct 2 - Oct 5

found 7 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

9.6/10 Exceptional! (1,696 reviews)

Great ATMOSPHERE

Reviewed on Aug 14, 2026

Hyatt Regency Coconut Point Resort & Spa

CA $1,367

per person

Oct 2 - Oct 5

found 7 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

The staff

Reviewed on Aug 14, 2026

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See all available trips from Columbus to Southwest Florida

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4 Night Pet-friendly holidays in Southwest Florida

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

Quality Inn Fort Myers Cape Coral

CA $581

per person

Oct 22 - Oct 26

found 7 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

7.6/10 Good! (396 reviews)

NEVER STOP BY IT AGAIN I CHECK IN SATURDAY TO CHECK OUT FRIDAY 08/15 EVERYONE. IN FRONT DESK SAID SOMEONE WIL BE TAKING CARE A SMALL PROBLEM TV DOESN'T WORK I DID A REPORT TWO TIMES A DAY BY THE END NOT BODY FIXED IT THAT WAY I MOVING TO AN OTHER HOTEL WHICH TAKE CARE ME

Reviewed on Aug 14, 2026

Tween Waters Island Resort & Spa

CA $1,268

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Was able to watch the dolphins in the morning from the balcony. Short walk across the street to the beach and they have umbrellas and chairs to rent. Would definitely come back.

Reviewed on Aug 13, 2026

The Lighthouse Resort Inn & Suites

CA $955

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Fort Myers (RSW)

8.6/10 Excellent! (1,747 reviews)

We had a great time at the Lighthouse. The room we were in was a little worn, flooring in living room area needs to be replaced as well as the counter tops. However, these things did not affect our stay and we did enjoy ourselves.

Reviewed on Aug 14, 2026

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Pet-friendly 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! (5,837 reviews)

"No microwaves in the room. They have one in the lobby but very inconvenient. Other than that a great place for a good price"

Reviewed on Aug 14, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

41 min drive from Siesta Key Beach

Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

9.4/10 Exceptional! (2,464 reviews)

"Great 👍"

Reviewed on Aug 14, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

1 hour drive from Siesta Key Beach

Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (3,197 reviews)

"Always a great stay! Especially as a solo traveler!"

Reviewed on Aug 14, 2026

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.