Holiday rentals in Oldsmar
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oldsmar
Guests agree: these stays are highly rated for location, cleanliness and more.
Modern Private Estate | Central to Tampa & Beaches
Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!
Sunny Oasis: Villa Retreat
Welcome to a stunning 2-bedroom, 2-bathroom villa nestled in the heart of sunny Florida! Whether you're seeking a relaxing beach getaway or exploring all that Florida has to offer, this villa is your perfect destination. Located 15-20 minutes from the beach in a prime location, you'll find a plethora of dining, shopping, and entertainment options nearby, ensuring there's something for everyone to enjoy. Book your stay today and experience the ultimate in comfort, convenience, and coastal charm.
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
Guest Favorite Waterview- 2 bed/2 bath apt w/pool
This 2 bed 2 bath condo is located in a quiet peaceful golf course neighborhood yet minutes from shopping & AMC theatre! Enjoy amazing sunsets and wonderful water view of large pond from the spacious balcony. Pool is just steps away from condo. Honeymoon Island Park 8 miles, beaches 16 miles. Enjoy your stay w/ complimentary wifi & many other amenities! Please let us know how to make your stay as comfortable as possible. Message w/ any questions we may be able to accommodate shorter stays.
Cozy 4BR Retreat|Near Busch Garden beach & TPA
Welcome to our beautiful newly built 2022 two-story home, perfect for families, business travelers, or group getaways. This spacious home features: ✔ 4 comfortable bedrooms ✔ 3.5 bathrooms ✔ Sleeps up to 8 guests ✔ Fully equipped modern kitchen ✔ Private patio with BBQ grill ✔ Fast WiFi ✔ Free parking Located in a peaceful neighborhood, only: 📍20 mins to Tampa Airport 📍30 mins to Clearwater Beach and Honeymoon Island beach 📍35 mins to Busch garden 📍Near shopping, restaurants & parks
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.
Oceanfront Escape | Private Beach | Cozy & Quiet
Hosted by Lala Premier Properties, Beauty on the Beach! Whether you're on vacation with the family, or traveling for work, this is your perfect home away from home! A 15 minute drive to westshore mall and other fun activities. A 30-minute drive to Bush Gardens, Adventure Island, Curtis Hixon Park, Downtown Tampa, Amalie Arena, Florida Aquarium, Cruise ports, Hyde Park, Ybor City, Channelside and the University of Tampa. A 20-minute drive to the Airport and International Mall.
Clearwater Studio Getaway
Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!
Palm Harbor Pet-Friendly Retreat Near Honeymoon Is
This newly renovated and peaceful Duplex-home in Palm Harbor offers a spacious layout perfect for families to gather and relax. Centrally located, it is just a short distance from popular Cities, restaurants, bars, shopping malls, and more. Only twelve minutes from the famous city of Dunedin and Tarpon Springs, 25 minutes to the renowned Clearwater Beach, and 20 minutes to Tampa International Airport, making it an ideal spot for both relaxation and adventure
A perfect Lake House get away
Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team
Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport
Louisa's Cottage
This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.
Popular amenities for Oldsmar holiday rentals
Other great holiday rentals in Oldsmar
Beach Style Villa Near Dunedin & Honeymoon Island
Sunny's Retreat
Quiet Safety Harbor Retreat Near Clearwater Beach
Cozy Private 2BR FL condo
Cozy 3/2 residential with free parking on premises
Coastal Cottage | Top 1% Airbnb Worldwide
2 Bed 2 Bath Remodeled House Palm Harbor
Peaceful Hideaway
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $242 SGD | $251 SGD | $259 SGD | $210 SGD | $205 SGD | $199 SGD | $199 SGD | $212 SGD | $190 SGD | $201 SGD | $212 SGD | $214 SGD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Oldsmar?
Accommodations near waterfront parks and in quiet residential neighborhoods are often preferred by visitors seeking a relaxing atmosphere. Many guests also look for stays that provide convenient access to local restaurants and recreation areas.
What are the best things to do in Oldsmar with kids?
Oldsmar has parks with playgrounds, shaded picnic areas, and walking trails where children can explore nature. Kids often enjoy interactive exhibits at local nature centers, as well as seasonal family-friendly events hosted around town.
What are some of the best things to do in Oldsmar?
Oldsmar has nature trails, waterfront parks, and local markets to explore. Outdoor recreation, birdwatching, and discovering nearby arts venues are frequently suggested by guests and residents alike.
How is the weather in Oldsmar?
Oldsmar generally has mild winters around 53–74°F (12–23°C) and warm, humid summers near 77–91°F (25–33°C) with frequent afternoon showers. Rain tends to increase from late spring through early fall, while winter and spring see more sunshine.
When is the best time to visit Oldsmar?
Late fall through spring is often recommended for warm days and lower rainfall, with temperatures generally from 53–83°F (12–28°C). Summer brings high humidity and heavier rains, along with lush green landscapes.
What are the best places to visit in Oldsmar?
Nature lovers often explore Mobbly Bayou Wilderness Preserve and R.E. Olds Park, while local history enthusiasts visit interpretive centers or heritage museums. The area also has unique open-air markets and performance spaces.
What are some hiking trails in Oldsmar?
Guests frequently explore nature trails at Mobbly Bayou Wilderness Preserve, which features boardwalks along the bayou and forested paths. Other parks in Oldsmar have short walking loops suitable for various activity levels.
What are some family activities we can do in Oldsmar?
Families frequently explore waterfront parks, enjoy playgrounds, or visit nature preserves around Oldsmar. The area also has recreational facilities and community centers that host programs suitable for guests of all ages.
What are some of the best day trip ideas from Oldsmar?
Many visitors plan day trips to nearby Gulf beaches, botanical gardens, or lively art districts in neighboring cities. Exploring regional wildlife refuges and historic downtowns is also frequently suggested for a broader experience.
Are there any pet friendly accommodations available in Oldsmar?
Many accommodations in Oldsmar welcome pets, with hosts often providing amenities like fenced yards or easy access to parks. Checking individual listings for detailed pet policies can help find the right fit for your travel companions.
What are some local tips for visiting Oldsmar?
Locals suggest bringing sun protection, exploring early in the day during summer, and sampling fresh seafood at waterfront eateries. Attending a local market or festival is also a great way to experience the community’s welcoming spirit.
What is Oldsmar known for?
Oldsmar is known for its waterfront parks, nature preserves, and strong ties to automotive history, named after Ransom E. Olds. The city hosts community gatherings, outdoor activities, and is recognized for its welcoming, small-town feel.
What are the best hidden gems to explore in Oldsmar?
Hidden gems around Oldsmar include quiet nature preserves with birdwatching platforms, community gardens, and art spaces featuring local creators. Smaller waterfront parks offer a peaceful atmosphere for unwinding or photography.
What are the best foods to try in Oldsmar?
Fresh Gulf seafood, grouper sandwiches, and Southern-style barbecue are frequently suggested local flavors. Many visitors also sample Cuban sandwiches and key lime pie, reflecting Oldsmar’s mix of culinary influences.
What should I bring for a trip to Oldsmar?
Pack lightweight clothing, comfortable walking shoes, and sun protection such as hats or sunscreen. If visiting during summer, a rain jacket or umbrella is helpful, and insect repellent can make time outdoors more comfortable.
What is the nightlife in Oldsmar like?
Oldsmar’s nightlife tends to be relaxed, with casual pubs, live music venues, and restaurants featuring local musicians or karaoke nights. Around the city, guests sometimes find seasonal outdoor events and family-oriented evening gatherings.
What are the most popular events or festivals in Oldsmar?
Oldsmar celebrates with community festivals, outdoor concerts, and car shows, especially around late winter and early spring. Seasonal markets and multicultural heritage events are also frequently hosted in city parks.
Are there family friendly vacation rentals in Oldsmar?
You will find many family-friendly rentals in Oldsmar, often with features like multiple bedrooms, kitchens, and access to parks or playgrounds. Filtering for amenities such as outdoor space or cribs can help tailor your search.
Quick stats about holiday rentals in Oldsmar
Total holiday rentals
Explore 130 holiday rentals in Oldsmar
Nightly prices starting at
Oldsmar holiday rentals start at $26 SGD per night before taxes and fees
Verified guest reviews
Over 4,020 verified reviews to help you choose
Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 70 rentals that welcome pets
Holiday rentals with a pool
80 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
120 of Oldsmar holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oldsmar rentals
4.8 Average rating
Oldsmar stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Destin Holiday rentals
- Fitness-friendly rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Hotel rooms Oldsmar
- Rentals with a fireplace Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a hot tub Oldsmar
- House rentals Oldsmar
- Rentals with pools Oldsmar
- Family-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a firepit Oldsmar
- Rentals with beach access Oldsmar
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Weeki Wachee Springs
- Bean Point Beach
- Coquina Beach
- Amalie Arena
- Tampa Convention Center
- Vinoy Park
- Sand Key Beach
- Dunedin Beach
- Cortez Beach
- Hard Rock Casino
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- River Strand Golf and Country Club
- University of South Florida
- Busch Gardens
- ZooTampa at Lowry Park
- North Beach At Fort DeSoto Park