Top Pet-friendly vacation packages in Southwest Florida

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

Compass by Margaritaville Hotel Naples

Central Naples

$823

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

White Plains (HPN) to Fort Myers (RSW)

9.6/10 Exceptional! (1,891 reviews)

Excelente servicio

Reviewed on Nov 14, 2026

The Westin Cape Coral Resort At Marina Village

Pelican

$1,308

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip flight included

Columbus (LCK) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

Hyatt Regency Coconut Point Resort & Spa

$1,196

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Detroit (DTT) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

3 Night Pet-friendly vacations in Southwest Florida

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

Compass by Margaritaville Hotel Naples

Central Naples

$823

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

White Plains (HPN) to Fort Myers (RSW)

9.6/10 Exceptional! (1,891 reviews)

Excelente servicio

Reviewed on Nov 14, 2026

The Westin Cape Coral Resort At Marina Village

Pelican

$1,308

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip flight included

Columbus (LCK) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

Hyatt Regency Coconut Point Resort & Spa

$1,196

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Detroit (DTT) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

4 Night Pet-friendly vacations in Southwest Florida

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

Hibiscus Suites - Gateway to Siesta Key

$744

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Flint (FNT) to Tampa (TPA)

8.8/10 Excellent! (2,471 reviews)

Tween Waters Island Resort & Spa

$768

per person

Dec 16 - Dec 20

found 3 hours ago

Roundtrip non-stop flight included

Portland (PWM) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Hyatt House Naples/5th Avenue

Old Naples

$1,090

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (2,175 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

Top Pet-friendly Southwest Florida Hotels

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

20 min drive from Siesta Key Beach

This pet-friendly hotel welcomes dogs (fees apply).

9.2/10 Wonderful! (6,266 reviews)

"My husband and I stayed at Kompose for a week for our honeymoon. The hotel was clean, comfortable, and quiet. The staff were all friendly and the buffet breakfast was great. The convenient location near the airport is unbeatable and we will definitely stay again next time we visit Sarasota."

Reviewed on Nov 14, 2026

Cottages at Siesta Key Inn

1105 Point of Rocks Rd Siesta Key FL

29 min walk from Siesta Key Beach

This pet-friendly hotel welcomes dogs (fees apply).

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

13 min walk from Siesta Key Beach

Stay at this resort in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...

9.2/10 Wonderful! (1,199 reviews)

"Only complaint is that there was not enough storage for clothes."

Reviewed on Nov 13, 2026

See all 48,065 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.