
Pet-friendly vacation rentals in Oldsmar
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Oldsmar
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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

Villa Key West "Villas by Christine"
Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

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!

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.

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!

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 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.

Entire Guest House near Tampa airport
Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

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.

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.

Walk to Main St and Waterfront, Mins to Beaches
Experience modern coastal luxury at this designer 2-bedroom, first-floor cottage in Downtown Dunedin. Steps from Main Street and a short stroll to waterfront sunsets, shops, restaurants, and nightlife. Minutes to Honeymoon Island, Caladesi Island, and Clearwater Beach. Beautifully designed and fully stocked for families, pets, and beach days. Treat yourself to the perfect coastal getaway at Barefoot Parrot Cottages.
Popular amenities for Oldsmar pet-friendly home rentals
Pet-friendly house rentals

Harbor Breeze Hideaway 4/2 King size bed!

3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

Modern Pet-Friendly Beach House w/ Heated Pool & S

Oceanfront Escape | Private Beach | Cozy & Quiet

Rooms with a Pool

2 Bed 2 Bath Remodeled House Palm Harbor

Serenity Bungalow Downtown

Peaceful Hideaway
Pet-friendly home rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

ST Urban Oasis heated pool

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Mermaid cottage

Oldsmar fully furnished home/ pet friendly
Private, pet-friendly home rentals

Casual, relaxing 2/2 SFH remodeled, in Dunedin.

"Blue Heron" Charming walkable downtown bungalow

House in Oldsmar near Clearwater / Tampa Hot tub*

Dunedin 2BR 2 bath NewBuild

Suite Sunshine - An Artist's Delight

Gulf View on Bay: Newly Renovated

Waterfront Gem Near Clearwater • Swim Spa + Nature

Paradise Palms- Pet Friendly home with Game Room!
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 632 | ﺩ.ﺇ 731 | ﺩ.ﺇ 742 | ﺩ.ﺇ 591 | ﺩ.ﺇ 588 | ﺩ.ﺇ 551 | ﺩ.ﺇ 547 | ﺩ.ﺇ 551 | ﺩ.ﺇ 544 | ﺩ.ﺇ 569 | ﺩ.ﺇ 606 | ﺩ.ﺇ 577 |
| 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 |
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 ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 2,170 verified reviews to help you choose

Family-friendly vacation rentals
40 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!
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- Family-friendly rentals Oldsmar
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- House rentals Oldsmar
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- Hotel rooms Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with a hot tub Oldsmar
- Pet-friendly rentals Pinellas County
- Pet-friendly rentals Florida
- Pet-friendly rentals United States
- Anna Maria Island
- Raymond James Stadium
- Weeki Wachee Springs
- Anna Maria Island Beach
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