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

$709

per person

Jan 10 - Jan 15

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.6/10 Exceptional! (1,891 reviews)

Very enjoyable stay! We felt welcome right at check in. The room was clean, spacious and attractively decorated. Breakfast was very tasty. The hotel decor really makes you feel like you’re on a vacation in Florida.

Reviewed on Nov 10, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,684

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

The Westin Cape Coral Resort At Marina Village

Pelican

$1,650

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

first class property and staff

Reviewed on Nov 9, 2026

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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

$608

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,891 reviews)

Very enjoyable stay! We felt welcome right at check in. The room was clean, spacious and attractively decorated. Breakfast was very tasty. The hotel decor really makes you feel like you’re on a vacation in Florida.

Reviewed on Nov 10, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,271

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

9/10 Wonderful! (1,001 reviews)

The Westin Cape Coral Resort At Marina Village

Pelican

$1,559

per person

Jan 14 - Jan 17

found 2 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

first class property and staff

Reviewed on Nov 9, 2026

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See all available trips from Columbus to Southwest Florida

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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

$529

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

8.8/10 Excellent! (2,471 reviews)

Clean rooms, great staff, air condition, jumping, great parking available

Reviewed on Nov 10, 2026

Hyatt House Naples/5th Avenue

Old Naples

$938

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.2/10 Wonderful! (2,175 reviews)

Tween Waters Island Resort & Spa

$704

per person

Jan 10 - Jan 14

found 20 hours ago

Roundtrip flight included

Milwaukee (MKE) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Very relaxing.

Reviewed on Nov 10, 2026

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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).

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! (1,198 reviews)

"This was our first time here and we very much enjoyed it! Facility was very nice. Rooms were clean updated pool area was nice. I would recommend."

Reviewed on Nov 10, 2026

See all 47,961 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.