
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

Cabin 3 - Nasturtium Nest
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. We look forward to seeing you on the Farm!

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.

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.

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!

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!

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!

Private apartment perfectly located in Citrus park
A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

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!

Tropical Oasis Retreat w/ Heated Pool
Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

Mins to Beach/Studio Home/walk to dwtn/FreeParking
✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.
Popular amenities for Oldsmar pet-friendly home rentals
Pet-friendly house rentals

The House of Relaxation

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

Lakefront home near beaches w/ waterview, pets ok

Our Gemini Place: Comfort & Charm in Old Tarpon

Home away from Home

Clearwater House!Near the beach!Newly renovated!

Cozy Retreat! Walk to Crystal Beach/Park

Modern Private Estate | Central to Tampa & Beaches
Pet-friendly home rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Entire house in Tampa w/ Heated POOL!

The Pearl at Ridgewood Park

Downtown Dunedin B&B - Rustic Cabin Studio with He

Luxury Beach Bungalow | Walk to Dining & Sunset

Private pool suite in heart of Tarpon Springs!

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

Mermaid cottage
Private, pet-friendly home rentals

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

Flat Bay Dr

Palm Harbor Renovated Hideaway!

Lovely Sunrise

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

Suite Sunshine - An Artist's Delight

Cozy Quiet Apt| Washer/Dryer | Minutes to Airport

Palm Harbor Retreat | 2BR/2BA Near Gulf Coast Fun
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $210 CAD | $229 CAD | $228 CAD | $220 CAD | $218 CAD | $205 CAD | $203 CAD | $205 CAD | $202 CAD | $211 CAD | $225 CAD | $214 CAD |
| 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 $41 CAD per night before taxes and fees

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

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

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Oldsmar vacation rentals include wifi 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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- Hotel rooms Oldsmar
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- Rentals with pools Oldsmar
- House rentals Oldsmar
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- Rentals with a patio Oldsmar
- Pet-friendly rentals Pinellas County
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- Anna Maria Island
- Raymond James Stadium
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