Become a host

Vacation rentals in Oldsmar

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oldsmar

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

%{current} / %{total}1 / 1
Top 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
4.97 out of 5 average rating, 178 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
The exterior of a newly constructed barn loft apartment is shown, featuring a wraparound deck accessed by wooden stairs. Beneath the deck, picnic tables and seating areas are visible among the surrounding greenery and trees. The property is set in a spacious outdoor environment.
Barn in Odessa
4.99 out of 5 average rating, 148 reviews

Cypress Lakes Barn Retreat

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

Top guest favorite
An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.
Tiny home in Dade City
4.98 out of 5 average rating, 215 reviews

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

Top guest favorite
Cottage in Lutz
4.97 out of 5 average rating, 141 reviews

A little piece of Heaven

2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

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
4.83 out of 5 average rating, 156 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
4.71 out of 5 average rating, 112 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.

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, 158 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

Top guest favorite
Home in Palm Harbor
4.98 out of 5 average rating, 110 reviews

Tarpon Lake Escape LLC

Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Top guest favorite
The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.
Cottage in Oldsmar
4.96 out of 5 average rating, 315 reviews

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.

Guest favorite
The exterior of a transformed school bus is displayed in a garden setting, surrounded by greenery. Warm lights illuminate the entrance, which features a wooden deck with seating. A stone path leads to the bus, enhancing the natural ambience of the private outdoor area.
Tiny home in Palmetto Beach
4.97 out of 5 average rating, 124 reviews

Cozy AF Medusa the Bus-Lux

Welcome to the Cozy AF Medusa: The Bus Lux! This one-of-a-kind school bus has been transformed into a luxurious tiny house, handcrafted with custom 3D-printed designs and Medusa-inspired decor. Every corner has been thoughtfully designed to tell a story, making your stay as immersive as it is unforgettable.

Guest favorite
A charming cottage exterior is framed by lush greenery and palm trees, with a welcoming blue front door. A stone pathway leads to the entrance, surrounded by an inviting garden. The cottage is nestled within a fenced yard, providing a sense of privacy.
Home in Dunedin
4.9 out of 5 average rating, 130 reviews

BeachBunkies Cottage 1. Four miles to the beach!

Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.

Guest favorite
The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.
Home in Oldsmar
4.85 out of 5 average rating, 116 reviews

Modern & Spacious Retreat with Private Pool!

Welcome to our exquisite Airbnb in Oldsmar, Florida, where luxury and convenience converge in a SINGLE-story haven. This delightful getaway promises an unforgettable stay for travelers seeking relaxation, outdoor adventures, and a touch of historical charm.

Popular amenities for Oldsmar vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Oldsmar's top sights

Philippe Park

97 locals recommend

John Chestnut Senior Park

59 locals recommend

Oldsmar Flea Market

44 locals recommend

Empower Adventures Tampa Bay

59 locals recommend

AMC Theatres-Woodlands Square 20

28 locals recommend

R E Olds Park

28 locals recommend

Other great vacation rentals in Oldsmar

Guest favorite
Home in Dunedin
4.81 out of 5 average rating, 42 reviews

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

Guest favorite
Home in Safety Harbor
4.88 out of 5 average rating, 95 reviews

Nice Sparkling Clean Home with Pool.

Guest favorite
A selection of woven storage baskets is displayed on a countertop, featuring neatly arranged napkins and two water bottles. A decorative sign reading 'HOME SWEET HOME' adds a personal touch to the arrangement, blending function with a welcoming aesthetic.
Home in Palm Harbor
5 out of 5 average rating, 27 reviews

Palm Harbor Renovated Hideaway!

Top guest favorite
An inviting pool area is visible, enclosed by a screened lanai that allows for unobstructed views of the surrounding landscape. Comfortable seating arrangements are placed adjacent to the pool, while a coffee table displays a decorative arrangement, enhancing the relaxing atmosphere.
Vacation home in Safety Harbor
4.84 out of 5 average rating, 92 reviews

4-bedroom Vacation home with heated pool family

Top guest favorite
Home in Palm Harbor
5 out of 5 average rating, 6 reviews

Gulf View on Bay: Newly Renovated

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, 63 reviews

Safety Harbor Cottage

Guest favorite
The two-story townhome features a welcoming exterior with large windows framed by black shutters. A manicured landscape surrounds the entrance, which is highlighted by a single door with decorative lighting. The serene evening sky adds a gentle backdrop to the setting.
Townhouse in Tampa
4.86 out of 5 average rating, 49 reviews

Tampa Townhome Getaway • Westchase & Citrus Park

Top guest favorite
Home in Palm Harbor
5 out of 5 average rating, 13 reviews

2BR Quiet House-King Adjustable Bed-Garden-BBQ

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ694ﺩ.ﺇ720ﺩ.ﺇ742ﺩ.ﺇ602ﺩ.ﺇ588ﺩ.ﺇ569ﺩ.ﺇ569ﺩ.ﺇ606ﺩ.ﺇ544ﺩ.ﺇ577ﺩ.ﺇ606ﺩ.ﺇ613
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.

Quick stats about vacation rentals in Oldsmar

  • Total vacation rentals

    Explore 130 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 4,020 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 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

    120 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!

Destinations to explore

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