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Vacation rentals in Oldsmar

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Quick stats about vacation rentals in Oldsmar

  • Total vacation rentals

    Explore 140 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at €18 per night before taxes and fees

  • Verified guest reviews

    Over 4,090 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Oldsmar vacation 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 vacation rentals in Oldsmar

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
Home in Oldsmar
4.8 out of 5 average rating, 87 reviews

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.

Top guest favorite
Home in Oldsmar
4.98 out of 5 average rating, 42 reviews

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!

Top guest favorite
An outdoor patio area features a shaded table surrounded by four adirondack chairs. A tropical palm tree adds greenery, and a grilling station is positioned nearby. The space is enclosed by a white fence and showcases a well-maintained lawn.
Home in Oldsmar
4.96 out of 5 average rating, 90 reviews

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.

Guest favorite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.95 out of 5 average rating, 192 reviews

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

Top guest favorite
A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.
Guesthouse in Westchase
4.99 out of 5 average rating, 102 reviews

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.

Top guest favorite
The charming guest house exterior is framed by a lush green lawn. A walkway leads to a welcoming front door, with two comfortable chairs positioned by the entrance. Large windows allow natural light into the space, complemented by a well-maintained garden area.
Guesthouse in Palm Harbor
4.98 out of 5 average rating, 100 reviews

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!

Guest favorite
An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.
Guesthouse in Dunedin
4.84 out of 5 average rating, 161 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Guest favorite
A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.
Home in Oldsmar
4.72 out of 5 average rating, 113 reviews

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.

Guest favorite
Home in Oldsmar
4.92 out of 5 average rating, 12 reviews

Oldsmar Oasis

Enjoy a peaceful stay in this 2 bed, 2 bath condo in quiet, gated East Lake Woodlands Neighborhood. Features a king bed and bunk beds—perfect for families. Relax by the community pool or unwind after a day exploring. Conveniently located off Tampa Rd, just minutes from shopping, dining, a movie theater, and Tampa Bay Downs. Only 20 minutes from the Tampa International Airport. Ideal for short getaways or extended stays with all the comforts of home.

Top guest favorite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 166 reviews

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

Guest favorite
Home in Oldsmar
4.9 out of 5 average rating, 31 reviews

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 !

Top guest favorite
Guesthouse in Safety Harbor
4.94 out of 5 average rating, 314 reviews

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 vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Oldsmar's top sights

Philippe Park

99 locals recommend

John Chestnut Senior Park

60 locals recommend

Oldsmar Flea Market

44 locals recommend

Empower Adventures Tampa Bay

59 locals recommend

AMC Theatres-Woodlands Square 20

29 locals recommend

R E Olds Park

28 locals recommend

Other great vacation rentals in Oldsmar

Superhost
Home in Oldsmar
4.88 out of 5 average rating, 8 reviews

House in Oldsmar near Clearwater / Tampa Hot tub*

Guest favorite
The exterior of a two-story condo is showcased, featuring a well-maintained entrance with a concrete pathway bordered by lush green grass. The building has multiple windows and a combination of beige and brown siding, along with a row of palm trees enhancing the tropical setting.
Apartment in Oldsmar
4.92 out of 5 average rating, 26 reviews

Cozy Private 2BR FL condo

Guest favorite
A screened-in balcony area is visible, showcasing views of a large pond surrounded by lush greenery. Bright blue skies and scattered clouds reflect a serene atmosphere. Two striped chairs are positioned for relaxation, set against the tiled floor surrounded by wooden railings.
Condo in Oldsmar
4.88 out of 5 average rating, 33 reviews

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

Superhost
Home in Oldsmar
5 out of 5 average rating, 3 reviews

Tropicoquette|Beach|Pool|Airport|Clearwater|STPete

Superhost
Home in Safety Harbor
4.6 out of 5 average rating, 5 reviews

Sunny Haven -Family Friendly 3BR/2BTH Getaway

Top guest favorite
A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.
Villa in Palm Harbor
5 out of 5 average rating, 49 reviews

Coastal Cottage | Top 1% Airbnb Worldwide

Top guest favorite
Condo in Oldsmar
5 out of 5 average rating, 8 reviews

Short Drive to Clearwater Beach | Heated Pool

Top guest favorite
A contemporary cottage is illuminated at night, showcasing large glass panels that reveal a warm interior. Surrounding the cottage, a manicured lawn features stone pathways and lush greenery, creating a serene outdoor environment.
Cottage in Safety Harbor
5 out of 5 average rating, 66 reviews

Safety Harbor Cottage

When is the best time to visit Oldsmar?

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Avg. price€166€172€177€144€140€136€136€145€130€138€145€146
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Oldsmar