Airbnb your place

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 favourite
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, 180 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 favourite
A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.
Farm stay in Odessa
4.97 out of 5 average rating, 115 reviews

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!

Guest favourite
Guesthouse in Dunedin
4.83 out of 5 average rating, 157 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 favourite
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 favourite
A peaceful outdoor area is surrounded by lush greenery, featuring palm trees and vibrant plants. A simple table and chairs are positioned beneath a canopy, providing a shaded space for relaxation. A whimsical flamingo decoration adds a playful touch to the serene environment.
Guest suite in Clearwater
5 out of 5 average rating, 105 reviews

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!

Guest favourite
Home in Palm Harbor
4.95 out of 5 average rating, 193 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and three TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

Top guest favourite
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, 159 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 favourite
A tiny home with a black wooden exterior is set on a gravel pathway. Two wooden chairs are positioned nearby, alongside a fire pit. The surrounding area features grass and trees, offering an open and tranquil atmosphere.
Tiny homes in Town 'n' Country
4.84 out of 5 average rating, 109 reviews

Pine Forest Cabin by Natl Park

Escape from it all and relax under the stars in this cozy Tiny Home, nestled on a serene 2-acre lot. Located alongside other units, which can be booked through separate listings, this tiny cabin offers the perfect getaway. Just a short walk from Upper Tampa Bay Park, where you can enjoy kayaking rentals, explore scenic trails, fishing, bike ride, and much more.

Top guest favourite
A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.
Cottage in Safety Harbor
4.92 out of 5 average rating, 106 reviews

Heart of Town Cottage with Hot Tub

Escape to a stylish designer cottage just one block from vibrant Main Street! Perfect for couples or small families, this private home offers a luxurious getaway. Enjoy a fully equipped kitchen, a dedicated workspace, and an incredible private backyard with a hot tub, fire pit, and gazebo. Experience upscale comfort in a prime, walkable location.

Top guest favourite
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 favourite
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 homes in Palmetto Beach
4.97 out of 5 average rating, 131 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 favourite
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, 117 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

KitchenWifiPoolFree parking on premisesAir 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 favourite
Home in Dunedin
4.81 out of 5 average rating, 42 reviews

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

Guest favourite
The exterior of a single-story house is presented, featuring a two-car garage and a well-maintained lawn. Lush green shrubs frame the entrance, and a small American flag is placed near the mailbox. A partly cloudy sky adds depth to the welcoming scene.
Home in Safety Harbor
4.88 out of 5 average rating, 95 reviews

Nice Sparkling Clean Home with Pool.

Guest favourite
A single-family home with a dark exterior is framed by lush greenery and palm trees. A spacious driveway leads to a two-car garage, while a vibrant lawn adds a touch of color. Large windows create a welcoming facade, showcasing the inviting entrance.
Home in Town 'n' Country
4.86 out of 5 average rating, 59 reviews

CasaBella

Top guest favourite
The kitchen area is designed with modern appliances and light cabinetry. A skylight overhead brings natural light into the space. Adjacent, a dining table is visible, and a cozy seating area is featured with a gray sofa and decorative pillows in soft hues.
Cottage in Safety Harbor
5 out of 5 average rating, 75 reviews

"Sweet Harbor Cottage" Walk to Downtown

Guest favourite
Home in Oldsmar
4.84 out of 5 average rating, 51 reviews

Sunny's Retreat

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

Cozy Villa Close to Tampa Bay & Clearwater Beaches

Top guest favourite
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, 46 reviews

Coastal Cottage

Guest favourite
Home in Ozona
5 out of 5 average rating, 6 reviews

Gulf View on Bay: Newly Renovated

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$259 CAD$269 CAD$277 CAD$225 CAD$219 CAD$212 CAD$212 CAD$226 CAD$203 CAD$215 CAD$226 CAD$229 CAD
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 $27 CAD 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 and 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

  • Wifi availability

    120 of Oldsmar vacation 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

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