Holiday houses in Oldsmar
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Quick stats about holiday rentals in Oldsmar
Total holiday rentals
Explore 140 holiday rentals in Oldsmar
Nightly prices starting at
Oldsmar holiday rentals start at $34 NZD per night before taxes and fees
Verified guest reviews
Over 4,090 verified reviews to help you choose
Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
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
Wi-Fi availability
130 of Oldsmar holiday rentals include Wi-Fi 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!
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!
Cozy 3/2 residential with free parking on premises
Welcome to stunning 3/2/2 home. Your family will be close to everything when staying at this centrally-located place. It's .3 mile to R.E. Olds Park, 1.5 mile to Mobbly Bayou Beach Park, 12 miles to TPA Airport, 15 miles to Clearwater Beach, 17 miles to Tampa Riverwalk, 18 miles Busch Gardens, 24 miles to St. Peterburg Beach. Long for Dim Sum while you're in Tampa: 13 miles Yummy House South China Bistro! Or Vietnamese food: 7 miles Thinh An Kitchen & Tofu, 11 miles SaiGon Deli & SGMarket.
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
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!
Cottage in Paradise.
Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.
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.
New Guesthouse with Pool in Palm Harbor
This Brand new Beautiful Guest house was completed in August 2024 and is located in the back corner of a 1/2 acre lot with all the amenities for a short stay or longer stay. From private access to the house and use of the shared pool and patio this house has it all! Full Kitchen, Dining Area, Living room, Washer and Dryer. Stunning Master Bedroom, Master Bath with Dual Vanity, Jacuzzi and walk in shower and spacious master closet. This Gem includes all the amenities for a Luxurious Stay!
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.
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
beautiful home oldsmar near to the beach
This is a beautiful and spacious home, located in Oldsmar, Pinellas County , Florida. It is perfect for family vacation or romantic getway, it is single family home with 3 bedrooms 2 bathrooms 2 car garage . it is minutes driving to the beaches , shopping and entertainment, walking distance to fine restaurants but still tucked way so very quiet, the neiborghood is very friedly and safe !
Tiny House Oasis - 2 Min Walk to Main Street
Experience unique tiny home living in the heart of downtown Safety Harbor! This stylish 132 sq. ft. retreat for two features soaring ceilings and a large, private outdoor oasis with a firepit and a one-of-a-kind outdoor shower. Just steps from Main Street's shops, restaurants, and the beautiful waterfront pier. Perfect for a memorable, walkable getaway.
Popular amenities for Oldsmar holiday rentals
Other great holiday rentals in Oldsmar
Modern Tropical Oasis • Heated Pool & Firepit
Cypress Place | Your Serene Retreat near Tampa!
Tropicoquette|Beach|Pool|Airport|Clearwater|STPete
Oldsmar Oasis
Short Drive to Clearwater Beach | Heated Pool
Cozy Private 2BR FL condo
House in Oldsmar near Clearwater / Tampa Hot tub*
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 | $325 NZD | $337 NZD | $347 NZD | $282 NZD | $275 NZD | $267 NZD | $267 NZD | $284 NZD | $255 NZD | $270 NZD | $284 NZD | $287 NZD |
| 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.
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- Rentals with a fireplace Oldsmar
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- Rentals with pools Oldsmar
- Family-friendly rentals Oldsmar
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