
Pet-friendly holiday 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

Taste Of Florida-10 mi from Tampa Airport
Welcome to our Taste of Florida! This wonderful, private little Coastal gem (nestled in Beautiful Carrollwood and only 10 miles from the airport) is perfectly located and equipped for vacationers, business travelers and those who just want to get away from the hustle and bustle. Whether you are visiting any of the nearby premier hospitals, theme parks, outlet malls or college campuses, this private in-law suite studio is sure to allow you to relax during your stay in the Tampa Bay Area.

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.

Relaxing beach gateway
Kick back and relax in this calm, stylish space.Only 5 miles from Clearwater beach! Newly renovated spacious studio with brand new bathroom and kitchenette! Spacious studio featuring 1 king bed, a fully equipped kitchenette , free 1 parking spot, high speed internet, flat screen TV. Quiet area located 5 min away from downtown Clearwater and steps away from beautiful park. There is also a dog park 5 minutes away. No smoking No parties Pets allowed 2 parking spot available

Charming Guest House in Tampa
Welcome to your cozy getaway in Tampa! Our guest house combines comfort and style, perfect for any traveler—whether visiting for leisure or work. Relax in a thoughtfully designed space featuring a peaceful bedroom, modern bathroom, and private patio ideal for morning coffee or unwinding in the evening. Nestled in a quiet neighborhood, you’re just minutes away from Tampa’s top attractions, dining spots, and beaches. Book your stay and let us make your visit truly memorable!

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 and experience the tranquility of country living!

Modern and Comfortable One Bedroom Studio
Welcome to our beautifully renovated studio, just 10 minutes from Tampa International Airport. Enjoy a private entrance, fully equipped kitchen, high-speed internet, Smart TV, a comfortable full-size bed, and a stylish bathroom. Perfectly located about 11 miles away from Tampa Downtown. Also Pet Policy: $65 for one pet; additional fees for more. Host Interaction: We're available for any needs or requests. Additional Details: Check-in: 3 PM Check-out: 11 AM

Cottage on Pinellas Bike Trail
This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

Cabin 1 - Marigold Moments
Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay.

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!

Luxe Apartment | Water Views | Covered Balcony
Upscale, comfortable suite located within central Safety Harbor. This beautiful apartment is great for a quick getaway or a longer vacation rental. Located steps away from Bayshore Blvd which borders Tampa Bay and a 10-minute walk to Main Street Safety Harbor. Beautifully professionally designed contemporary and comfy décor. Easily walk to many restaurants, breweries, and shops!

Downtown Dunedin B&B - Rustic Cabin Studio with He
Welcome to our STUDIO Rustic Cabin located in Downtown Dunedin & within easy walking distance to restaurants, breweries, shopping & everything Dunedin has to offer! Dunedin Stadium, home of Spring Training for the Toronto Blue Jays is just 1 mile away...easily walkable!
Popular amenities for Oldsmar pet-friendly home rentals
Pet-friendly house rentals

The Jungalow SOHO - Pool/Hot Tub

House of Relaxation

Boho Bungalow close to Downt- SOHO - Hyde P- TIA

SeaSalt Gray Cottage 1 - few miles to beaches

Rooms with a Pool

Home away from Home

NICE 1 BR/1 BA (+ 2BA W/D). 5 min DT, 10 beach!

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Pet-friendly home rentals with a pool

Luxury Beach Cottage | Walk to Dining & Sunset

The Pearl at Ridgewood Park

Beach or Relax | Heated Pool home/Spa | Pets OK

Lovely Condo minutes from beach & King bed

Seminole Heights Riverside Paradise w/Pool

Private apartment perfectly located in Citrus park

SHEEK and Glam- heated pool Updated! 3 mi to beach

Mermaid cottage
Private, pet-friendly home rentals

Comfy Guesthouse # 2 - 4 miles to Clearwater Beach

Flat Bay Dr

Charming Studio | Outdoor Kitchen | Free Parking

Private Beach Retreat

Lovely Sunrise

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

Suite Sunshine - An Artist's Delight

Modern Vintage Retreat | Walk downtown
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $221 AUD | $241 AUD | $240 AUD | $231 AUD | $230 AUD | $215 AUD | $214 AUD | $215 AUD | $212 AUD | $258 AUD | $215 AUD | $211 AUD |
| 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 holiday rentals that are pet-friendly in Oldsmar

Total holiday rentals
Explore 70 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $43 AUD per night before taxes and fees

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

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Oldsmar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Pet-friendly rentals Pinellas County
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club
- Fred Howard Park




