Pet-friendly vacation rentals in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this beloved Dunedin favorite!

Villa at Harbor House "Villas by Christine"

Welcome to The Villa at Harbor House, located just steps from Safety Harbor’s Main Street, ranked the #10 Main Street by USA Today in 2025. Enjoy convenient walkable access to charming shops, dining, and pubs. This villa is perfect for solo travelers or couples, offering a queen bedroom, fully stocked kitchen, spacious living room, smart TVs, full laundry, and more. Pet-friendly ($100 fee). Beach gear included. For larger groups, consider booking Villa Key West or Villa Italia, steps away.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today! Please note that the minimum age requirement to book is 23.

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Cozy Retreat! Walk to Crystal Beach/Park

Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and three TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

Heart of Town Cottage with Hot Tub

Escape to a stylish designer cottage just one block from vibrant Main Street! Perfect for couples or small families, this private home offers a luxurious getaway. Enjoy a fully equipped kitchen, a dedicated workspace, and an incredible private backyard with a hot tub, fire pit, and gazebo. Experience upscale comfort in a prime, walkable location.

Cozy AF Medusa the Bus-Lux

Welcome to the Cozy AF Medusa: The Bus Lux! This one-of-a-kind school bus has been transformed into a luxurious tiny house, handcrafted with custom 3D-printed designs and Medusa-inspired decor. Every corner has been thoughtfully designed to tell a story, making your stay as immersive as it is unforgettable.