Southwest Florida Pet-friendly Vacations 2026

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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

$1,017

per person

Dec 24 - Dec 28

found 15 hours ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.6/10 Exceptional! (1,842 reviews)

Great little place for what it costs. They have a morning shuttle to the beach, a nice pool, a great bar.

Reviewed on Oct 24, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,733

per person

Nov 24 - Nov 27

found 1 hour ago

Roundtrip flight included

Columbus (CMH) to Fort Myers (RSW)

9/10 Wonderful! (1,006 reviews)

The Westin Cape Coral Resort At Marina Village

Pelican

$1,381

per person

Nov 26 - Nov 28

found 18 hours ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

I would give great reviews but one thing that bothered me we prepaid for our stay at check out your are charged 40 dollars a day resort fee that was never mentioned. When I questioned it at check out was told nothing they can do and was like no big deal we stayed 6 nights that was 240 dollars I was a little upset was never mentioned at all … so please be aware of that fee they don’t tell you in advance.

Reviewed on Oct 19, 2026

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3 Night Pet-friendly vacations in Southwest Florida

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

The Westin Cape Coral Resort At Marina Village

Pelican

$1,051

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Reviewed on Oct 19, 2026

Compass by Margaritaville Hotel Naples

Central Naples

$1,376

per person

Dec 26 - Dec 29

found 21 hours ago

Roundtrip flight included

Flint (FNT) to Fort Myers (RSW)

9.6/10 Exceptional! (1,842 reviews)

Great little place for what it costs. They have a morning shuttle to the beach, a nice pool, a great bar.

Reviewed on Oct 24, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,733

per person

Nov 24 - Nov 27

found 1 hour ago

Roundtrip flight included

Columbus (CMH) to Fort Myers (RSW)

9/10 Wonderful! (1,006 reviews)

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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

$683

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Austin (AUS) to Tampa (TPA)

8.8/10 Excellent! (2,455 reviews)

Room was very clean, all furniture looked like new. Stuff was pleasant. Nice furnished room, living room and small kitchen. Love it

Reviewed on Oct 20, 2026

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$789

per person

Nov 23 - Nov 27

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

8.6/10 Excellent! (1,800 reviews)

Don’t trust the photos online; the shower curtain was disgusting and covered in mold, there was hair on the bed, and the TV was cracked down the middle—and they never replaced it. I do not recommend it.

Reviewed on Oct 24, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$688

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

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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 and cats (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).

8.8/10 Excellent! (289 reviews)

"Rooms were clean and Quiet. Enjoyed property"

Reviewed on Oct 23, 2026

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! (1,189 reviews)

"Awesome location, with a lot of extras. Comfy spacious suite with cold ac."

Reviewed on Oct 23, 2026

See all 48,200 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.