Southwest Florida Pet-friendly Vacations

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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

Compass by Margaritaville Hotel Naples

Central Naples
CA $1,194
per person
Oct 30 - Nov 6
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (1,819 reviews)
The Westin Cape Coral Resort At Marina Village

The Westin Cape Coral Resort At Marina Village

Pelican
CA $1,329
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
My husband and I chose this resort as our monthly get away. It is the sister hotel of the Currant Hotel. Our stay was very pleasurable and relaxing. This was our first stay here. I had read the reviews prior to staying here, and of course everyone cannot be pleased. I would suggest for younger couples with small children, that this resort isn't very child friendly due to not seeing any amenities for small children, teenagers will be fine. Our valet attendant who was a middle-aged Middle Eastern gentleman was absolutely amazing! This man truly valued his job. He stated he had been working for around eight months, and that his son was also an employee at the Resort. The food was decent, but I didn't understand how they would allow the restaurant to run out of shrimp on a Saturday at 1 p.m. The drinks were also good, not to strong, but worth the money. The only concern that I do have, is that housekeeping tried to enter our room after the doorbell was rang, but we had the latch lock on. When we opened the door there was no one there, and we didn't see a housekeeping cart or anything. I was left wondering who trying to get into our room being a key was used. My husband called the front desk and informed them what had happened. They promised to check into the inquiry and call back. The front desk called and confirmed that it was a housekeeper who badge showed that she/he had swiped our room door. Why would she come into our room if she didn't have any supplies.

Reviewed on Sep 29, 2026

Hyatt Regency Coconut Point Resort & Spa

Hyatt Regency Coconut Point Resort & Spa

CA $1,652
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
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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

Compass by Margaritaville Hotel Naples

Central Naples
CA $855
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,819 reviews)
Hyatt Regency Coconut Point Resort & Spa

Hyatt Regency Coconut Point Resort & Spa

CA $1,652
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
The Westin Cape Coral Resort At Marina Village

The Westin Cape Coral Resort At Marina Village

Pelican
CA $1,052
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
My husband and I chose this resort as our monthly get away. It is the sister hotel of the Currant Hotel. Our stay was very pleasurable and relaxing. This was our first stay here. I had read the reviews prior to staying here, and of course everyone cannot be pleased. I would suggest for younger couples with small children, that this resort isn't very child friendly due to not seeing any amenities for small children, teenagers will be fine. Our valet attendant who was a middle-aged Middle Eastern gentleman was absolutely amazing! This man truly valued his job. He stated he had been working for around eight months, and that his son was also an employee at the Resort. The food was decent, but I didn't understand how they would allow the restaurant to run out of shrimp on a Saturday at 1 p.m. The drinks were also good, not to strong, but worth the money. The only concern that I do have, is that housekeeping tried to enter our room after the doorbell was rang, but we had the latch lock on. When we opened the door there was no one there, and we didn't see a housekeeping cart or anything. I was left wondering who trying to get into our room being a key was used. My husband called the front desk and informed them what had happened. They promised to check into the inquiry and call back. The front desk called and confirmed that it was a housekeeper who badge showed that she/he had swiped our room door. Why would she come into our room if she didn't have any supplies.

Reviewed on Sep 29, 2026

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4 Night Pet-friendly holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

CA $748
per person
Nov 1 - Nov 5
found 10 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
8.6/10 Excellent! (1,790 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
CA $1,099
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

CA $1,080
per person
Nov 4 - Nov 8
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (2,452 reviews)
Suite was spotless, Casey (hostess & admin/ office, attendant) was extremely accommodating, Brian also). They provide everything one could need, friendly, cheerful. I highly recommend this hotel suite for anyone. I'm sure to be back.

Reviewed on Sep 28, 2026

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Pet-friendly Hotels in Southwest Florida

Kompose Boutique Hotel

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 ...
Kompose Boutique Hotel
Compass Hotel by Margaritaville Anna Maria Sound

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! (2,598 reviews)
"The hotel was very nice, the service was very good, and the breakfast was excellent; the only thing I didn't like was that the pool wasn't clean."

Reviewed on Sep 29, 2026

Compass Hotel by Margaritaville Anna Maria Sound
Cottages at Siesta Key Inn

Cottages at Siesta Key Inn

1105 Point of Rocks Rd Siesta Key FL
  • 29 min walk from Siesta Key Beach
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Siesta Key Beach and Lido Beach are located ...
8.8/10 Excellent! (276 reviews)
"there is someone at the desk sometimes but they can’t really help with much, other than check in and check out. they don’t have towels or anything like that you have to wait for house keeping"

Reviewed on Sep 27, 2026

Cottages at Siesta Key Inn
See all 47,615 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.

Things to do

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

CA $85
per adult
92% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Craft Beer and Wine Sunset Cruise in Palm Beach

Craft Beer and Wine Sunset Cruise in Palm Beach

CA $83
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Palm Beach: Floatilla Party Cruise

Palm Beach: Floatilla Party Cruise

CA $144
per adult
Palm Beach: Floatilla Party Cruise
See all activities in Southwest Florida

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.