
Keystone Pet-friendly Vacations
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Top Pet-friendly vacation packages in Keystone
Price found within the past 48 hours. Click for updated prices.





Wyndham Grand Clearwater Beach
Price was $1,362, price is now $920 per person
$920
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (4,000 reviews)
Just a grand place to stay at, the staff was friendly and helpful, the lobby area is amazing to hang out in, rooms and view were great and the best part of course is the location, which is absolutely central in Clearwater beach. An overall enjoyable stay with lots of nice photographs.
Reviewed on Nov 14, 2026
5* Pet-friendly vacations in Keystone
Price found within the past 48 hours. Click for updated prices.


The Gemma by Brightwild
Price was $5,875, price is now $5,184 per person
$5,184
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (7 reviews)
The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.
Reviewed on Jul 30, 2026

The St. Regis Longboat Key Resort
Price was $3,821, price is now $3,499 per person
$3,499
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (105 reviews)
I loved everything about the St.Regis, except that they didn’t give us an upgrade. It was very clear that the hotel was not even close to full.
Reviewed on Nov 12, 2026
3 Night Pet-friendly vacations in Keystone
Price found within the past 48 hours. Click for updated prices.



La Tortuga Historic Downtown Pass A Grille
Pass-a-Grille
Price was $1,413, price is now $990 per person
$990
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (37 reviews)
This property does not have a front desk concierge and the owners were extremely difficult to reach. I complained last week and still have not had a response other than an automated response.
We felt unsafe with some of the other guests on the property who appeared to be heavily intoxicated to the point we were ready to stay elsewhere and move our belongings. We ubered out for the evening. I’ve given the owners a fair amount of time to respond and am sorry to have to give a low rating. Towels were soiled and damp in the bathroom upon arrival and depending on which room you get, there are many steps to carry your luggage This was not clearly stated on the description.
Reviewed on Nov 11, 2026
4 Night Pet-friendly vacations in Keystone
Price found within the past 48 hours. Click for updated prices.



Cedar Cove Resort and Cottages
Price was $2,388, price is now $1,599 per person
$1,599
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (614 reviews)
What a treat for us Minnesotans!!! Special place to stay. Clean, comfy, and cozy! We stayed in the Violet Cottage. Staff allowed us to hang for a bit on the beach (plus parking for our rental) after check-out. There is even a shower available for this exact purpose, which is extra handy and appreciated. Thank you! We hope to be back some day!
Reviewed on Nov 9, 2026
Top Pet-friendly Keystone Hotels

4 Bedroom House with a Pool! 15 minutes from the TPA Airport!
Odessa FL
Stay at this vacation home in Odessa. Enjoy laundry facilities and air conditioning. Popular attractions Northdale Golf Course and Brooker Creek Headwaters Nature ...
9.2/10 Wonderful! (25 reviews)
"Great host! Eric went above and beyond to make our stay amazing. This would be my first choice anytime I am in this area again. The pool was wonderful. Very quiet and peaceful neighborhood. The host lives nearby and responded immediately to anything we needed. Best host ever!"
Reviewed on Sep 3, 2026

Feed Horses at Breakfast - Private Gated Cottage
Odessa FL
Stay at this cottage in Odessa. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Old McMicky's Farm and Crescent Lake are located ...
9.8/10 Exceptional! (80 reviews)
"The owner was very responsive, had a rotten step on the stairs, I asked him to replace it since it was a safety issue, and he replaced the board the next day. Also had a missing piece of wire to block off the area under the porch to prevent dogs from getting in. He put something up when he did the ..."
Reviewed on Oct 25, 2026

The Robins Nest|Lakefront Home w/ Pool & Theater
Odessa FL
Stay at this vacation home in Odessa. Enjoy private pools, a water park, and a garden. Popular attractions Lake Rogers Park and Old Memorial Golf Club are located ...
10/10 Exceptional! (3 reviews)
"Amazing stay , with amazing accommodations!Host stayed in touch when needed ! Beautiful home inside and out . 10/10 highly recommended !"
Reviewed on Aug 11, 2026
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

Starlite Infinity Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend

Clearwater Beach: Dolphin & Island Sandbar Cruise
$28
per adult
96% of travellers recommend

1.5-hour Dolphin Sightseeing Cruise from Tampa
$31
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















