
Pet-friendly vacation rentals in Oldsmar
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Oldsmar

Total vacation rentals
Explore 70 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at €17 per night before taxes and fees

Verified guest reviews
Over 2,060 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Oldsmar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated pet-friendly home rentals in Oldsmar
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Wonderful family friendly home in Dunedin FL
Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.
4.92 out of 5 average rating, 284 reviews
Heated saltwater pool|Spacious 4BR/3BA|
Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches. Happy holidays from our family to yours
4.96 out of 5 average rating, 134 reviews
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
4.96 out of 5 average rating, 202 reviews
Lakefront home near beaches w/ waterview, pets ok
Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!
4.93 out of 5 average rating, 131 reviews
Modern Paradise home near Clearwater Dunedin Beach
Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.
4.88 out of 5 average rating, 125 reviews
Walk Downtown and to Waterfront, Mins to Beaches
Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and indulgent stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s gorgeous waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.
4.97 out of 5 average rating, 390 reviews
Harbor Breeze Hideaway 4/2 King size bed!
Welcome to our beautiful city of Clearwater and to our unique Mid-Century modern style home. Centrally located within 20 minutes driving to the famous and award-winning Clearwater beach and 20 min driving to Tampa international airport. Easy access to local restaurants, bars, stores, super markets and mall. This comfortable home features unique design and layout with Mid-century modern furniture and decor, free Wi-Fi, smart TV’s, tile flooring; sleeps up to 10 people and has free parking.
4.98 out of 5 average rating, 106 reviews
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.
4.73 out of 5 average rating, 117 reviews
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.
4.91 out of 5 average rating, 236 reviews
Heated Pool 4 bed 7 miles to Honeymoon Island.
This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and 3 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.
4.94 out of 5 average rating, 201 reviews
Chic|Pool|PuttingGreen|Beaches
Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.
4.77 out of 5 average rating, 106 reviews
Hot Tub, Heated Pool, 2 Master Suites, Beach
Minutes from the beach is this fully renovated home with brand-new furniture. Enjoy an extra-large backyard with a hot tub, heated pool & plus a bonfire pit! Relax in the sunny Florida sunroom or park in the private double garage. Located in a quiet neighborhood, just minutes from Honeymoon Island and shopping centers. Strict no parties or events policy. Perfect for families and small groups seeking a peaceful, luxury getaway.
4.84 out of 5 average rating, 149 reviewsPopular amenities for Oldsmar pet-friendly home rentals
Pet-friendly house rentals

Dream Retro, Pets Welcome-fenced, near beaches
5.0 out of 5 average rating, 119 reviews
3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!
4.93 out of 5 average rating, 104 reviews
Cozy Retreat! Walk to Crystal Beach/Park
4.93 out of 5 average rating, 158 reviews
Peaceful Pet friendly 2 BR cottage with hot tub.
4.9 out of 5 average rating, 173 reviews
Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade
4.94 out of 5 average rating, 116 reviews
Modern Private Estate | Central to Tampa & Beaches
4.98 out of 5 average rating, 48 reviews
beautiful home oldsmar near to the beach
4.91 out of 5 average rating, 34 reviews
Modern Tropical Oasis • Heated Pool & Firepit
4.96 out of 5 average rating, 51 reviewsPet-friendly home rentals with a pool

Stunning South Tampa 6 Bedroom House
4.87 out of 5 average rating, 141 reviews
Cozy Tampa Home with Large Heated Pool
4.95 out of 5 average rating, 161 reviews
Family/Group Getaway w/ Pool Near Clearwater Beach
4.94 out of 5 average rating, 292 reviews
Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl
4.99 out of 5 average rating, 126 reviews
Angelita's Lake Home 3br3ba w/heated pool
4.99 out of 5 average rating, 100 reviews
Tampa | Heated Pool • Waterfront • Pet Friendly
4.82 out of 5 average rating, 104 reviews
Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr
4.95 out of 5 average rating, 136 reviews
Guest Favorite Waterview- 2 bed/2 bath apt w/pool
4.89 out of 5 average rating, 35 reviewsPrivate, pet-friendly home rentals

Luxe Apartment - Partial Water View - XL Balcony
4.98 out of 5 average rating, 124 reviews
Cabin 3 - Nasturtium Nest
4.96 out of 5 average rating, 118 reviews
Farm and lake stay at Maison de L'eau Douce
4.99 out of 5 average rating, 352 reviews
Paradise Palms- Pet Friendly home with Game Room!
4.88 out of 5 average rating, 66 reviews
Waterfront Gem Near Clearwater • Swim Spa + Nature
4.98 out of 5 average rating, 49 reviews
Luxe Harbor Haven: 5 bd Near Beaches, MLB + Golf
5.0 out of 5 average rating, 29 reviews
Heated Pool, Putting Green, Sleeps 6
4.9 out of 5 average rating, 41 reviews
Cozy Hen House Retreat
4.77 out of 5 average rating, 35 reviewsWhen is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €148 | €171 | €174 | €151 | €123 | €141 | €128 | €129 | €127 | €133 | €142 | €135 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
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