Best Vacation Homes in Oldsmar
House
10.0(41 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
AU $311/Night
7 Nights - AU $2,175
House
3 Bedrooms
2 Baths
12 Guests
2002.09 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $1,054/Night
7 Nights - AU $7,379
Hotel
9.4(1240 Reviews)
1 Bath
Pool- Balcony/Terrace
Breakfast
Kitchen
AU $153/Night
7 Nights - AU $1,072
Condo
10.0(22 Reviews)
2 Bedrooms
2 Baths
3 Guests
1096 ft²
- Fireplace/Heating
- Pool
- Kitchen
Parking
AU $229/Night
7 Nights - AU $1,603
Apartment
2 Bedrooms
2 Baths
6 Guests
904.17 ft²
Private Beach- Oceanfront
- Pool
- Ocean View
AU $156/Night
7 Nights - AU $1,091
House
10.0(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
AU $249/Night
7 Nights - AU $1,746
Condo
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
Pet Friendly
Air Conditioner
AU $370/Night
7 Nights - AU $2,593
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
AU $196/Night
7 Nights - AU $1,375
Oldsmar Luxury Rentals
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $1,207/Night
7 Nights - AU $8,448
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $1,207/Night
7 Nights - AU $8,448
Hotel
3 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $838/Night
7 Nights - AU $5,868
Hotel
3 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $838/Night
7 Nights - AU $5,868
House
10.0(14 Reviews)
4 Bedrooms
3 Baths
11 Guests
2900 ft²
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
AU $790/Night
7 Nights - AU $5,529
House
9.6(40 Reviews)
2 Bedrooms
2 Baths
6 Guests
1773 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $606/Night
7 Nights - AU $4,241
House
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $575/Night
7 Nights - AU $4,022
Hotel
2 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
AU $559/Night
7 Nights - AU $3,915
Oldsmar Pet Friendly Vacation Rentals
Condo
9.6(20 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $286/Night
7 Nights - AU $2,000
Hotel
9.1(315 Reviews)
9 Baths
344.44 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $182/Night
7 Nights - AU $1,276
Villa
9.4(132 Reviews)
2 Bedrooms
2 Baths
7 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $390/Night
7 Nights - AU $2,732
Hotel
8.4(163 Reviews)
1 Bath
538.19 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Pool
AU $164/Night
7 Nights - AU $1,150
New
Condo
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
AU $222/Night
7 Nights - AU $1,551
House
10.0(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $275/Night
7 Nights - AU $1,924
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $537/Night
7 Nights - AU $3,761
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $502/Night
7 Nights - AU $3,513
Oldsmar Large Vacation Homes
Villa
9.8(62 Reviews)
2 Bedrooms
2 Baths
4 Guests
1390 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $317/Night
7 Nights - AU $2,220
House
9.6(53 Reviews)
4 Bedrooms
3 Baths
16 Guests
1774 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $488/Night
7 Nights - AU $3,419
House
9.6(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
AU $410/Night
7 Nights - AU $2,873
House
9.4(18 Reviews)
3 Bedrooms
2 Baths
12 Guests
2000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $546/Night
7 Nights - AU $3,819
Villa
8.6(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $287/Night
7 Nights - AU $2,010
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
AU $263/Night
7 Nights - AU $1,839
Villa
6.0(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
AU $407/Night
7 Nights - AU $2,846
House
3.0(1 Review)
5 Bedrooms
3 Baths
16 Guests
- Pet Friendly
- Air Conditioner
Child Friendly
Bedding/Linens
AU $498/Night
7 Nights - AU $3,485
Why Choose Rent By Owner for your Oldsmar Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Oldsmar Vacation Rentals
Where are the best neighborhoods to stay in Oldsmar?
When choosing where to stay in Oldsmar, Florida, exploring the various neighborhoods can help you find the perfect setting for your vacation. Each area offers a unique atmosphere, whether you're seeking quiet residential streets, access to local parks, or proximity to the charming downtown district. Staying in a neighborhood that suits your preferences ensures a comfortable and memorable visit. With a range of dependable vacation rentals available across Oldsmar's diverse neighborhoods, you'll have no trouble finding a convenient location that enhances your Florida getaway.
East Lake Woodlands
This area offers a peaceful retreat with scenic views and easy access to outdoor activities, making it an ideal choice for those seeking relaxation near the region's natural beauty.
View 245+ Rentals in East Lake WoodlandsElw Woods Landing
Located close to key amenities and local attractions, this neighborhood provides a convenient base for exploring all that the region has to offer.
View 192+ Rentals in Elw Woods LandingQuail Forest
Known for its serene environment and lush landscapes, Quail Forest is perfect for visitors looking for a quiet and comfortable stay close to Oldsmar's vibrant community.
View 237+ Rentals in Quail ForestTurtle Creek
Offering a cozy atmosphere and scenic surroundings, Turtle Creek is a desirable destination for those wanting to enjoy the tranquility of the area.
View 151+ Rentals in Turtle CreekBest Times to Visit Oldsmar
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can greatly enhance your experience, as understanding the seasonal patterns in this destination ensures you find the perfect period to enjoy all that the region has to offer.
Peak Season Highlights
Spring (March to May)
During the spring months, you'll enjoy warm weather ideal for exploring this destination's outdoor activities and scenic beauty.
Average Temperature Daytime: around 75-85°F - Nighttime: approximately 55-65°F
Winter (December to February)
The winter season offers mild temperatures, making it a popular time for visitors seeking refuge from colder climates while enjoying outdoor leisure in the region.
Average Temperature Daytime: about 65-75°F - Nighttime: roughly 45-55°F
Off-Season Highlights
Summer (June to August)
In the summer, higher temperatures and increased humidity characterize the area, often resulting in fewer crowds and more affordable accommodation options.
Average Temperature Daytime: around 85-90°F - Nighttime: approximately 70-75°F
Fall (September to November)
Autumn sees a slight dip in tourist numbers, providing a quieter experience with pleasant weather suitable for exploring here at your own pace.
Average Temperature Daytime: about 75-85°F - Nighttime: roughly 55-65°F
Weekly Weather Forecast for Oldsmar
How to Book Your Oldsmar Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Oldsmar
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor lounging with private patios or decks to relax in the sunshine.
- Take advantage of a screened-in porch to unwind while staying protected from insects.
- Make the most of landscaped yards perfect for outdoor dining or family gatherings.
- Benefit from access to swimming pools, ideal for cooling off during warm days.
- Utilize outdoor grills and barbecue stations for cookouts with friends and family.
- Explore nearby walking or biking paths that allow you to enjoy the scenic beauty of the region.
- Relax in shaded areas with outdoor seating designed for enjoying the fresh air and views.
Top Attractions Around Oldsmar
What attractions are nearby?
Here in Oldsmar, Florida, USA, you can enjoy a variety of outdoor activities and scenic parks that showcase the natural beauty of the region, making it a perfect destination for relaxation and adventure during your stay.
Family Activities
- Oldsmar Community Park: Spend a fun-filled day outdoors enjoying the playgrounds, walking trails, and picnic areas designed for family activities in this scenic spot.
- Town Square Nature Park: Explore the lush, natural habitats here with your loved ones, perfect for leisurely walks and discovering local wildlife.
- Pinellas Trail: Cycle or walk along this popular trail that offers picturesque views and easy access to the region’s green spaces, ideal for active family outings.
- Oldsmar Escape Room: Test your family's problem-solving skills together by taking on exciting themed escape challenges located conveniently within the area.
Adult Activities
- Oldsmar Eco Adventure Park: Experience outdoor fun at this eco-friendly park, perfect for enjoying the natural beauty of the region.
- The Oldsmar Historical Society: Dive into local history and explore the area's past through engaging exhibits and guided tours.
- Tampa Bay Golf & Country Club: Play a round of golf on pristine courses designed to challenge and delight golfers of all skill levels.
- Pinellas Trail: Cycle or walk along this scenic trail that weaves through the region, offering stunning views and a peaceful escape.
Other Places to Stay in Oldsmar, FL
Z - A Specialty Spa
East Lake Woodlands
Quail Forest
Elw Woods Landing
Oldsmar Historical Society Museum
Oldsmar Flea Market
Advanced Primary Care
Turtle Creek
Oldsmar Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature Trails: Take advantage of the area’s scenic trails to enjoy outdoor activities and connect with the natural beauty surrounding your vacation rental.
- Visit Community Events: Check out nearby community events and markets, which offer authentic local experiences and a chance to meet residents during your stay.
- Plan Water-Based Activities: Make the most of the region's proximity to waterways by engaging in activities like kayaking or paddleboarding right from your vacation rental base.
- Discover Nearby Dining Options: Explore a variety of local restaurants and cafes that showcase the area's culinary flavors, perfect for relaxing after a day of sightseeing.
Transportation Options
- Rental Car Services: Conveniently explore the area with numerous rental car agencies offering flexible options for traveling to and from your vacation rentals in Oldsmar.
- Public Transit: Local bus services provide an affordable and reliable way to navigate the region around Oldsmar without the need for a personal vehicle.
- Taxis and Rideshare: Taxis and rideshare apps like Uber and Lyft are readily available, offering quick access to nearby attractions and amenities here.
- Biking and Pedestrian Paths: Well-maintained bike lanes and walking trails allow you to enjoy the region’s scenery at your own pace while staying active during your visit.
Local Customs Options
- Oldsmar's Citrus Harvest Festival: Celebrating the region’s rich agricultural roots, this festival showcases locally grown citrus fruits through lively markets and family-friendly events.
- Native American Heritage: The area honors its indigenous history with cultural exhibits and ceremonies that provide insight into the Native American influence on the region.
- Seafood Cuisine Traditions: Enjoy the local customs of fresh seafood preparation, reflecting the region’s coastal proximity and its maritime culinary heritage.
- Community Sports Events: Participating in or spectating at local sports tournaments offers a glimpse into the area's community spirit and active lifestyle.
Frequently Asked Questions About Oldsmar?
1. What are the top vacation rentals in Oldsmar?
There are a lot of options in Oldsmar. If you plan on staying in the Oldsmar area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oldsmar:
- Beautiful home in Oldsmar
- Coastal themed home near beach and airport
- Cozy Two Bedroom Condo Tucked Away In The Serene Settings Of East Lake Woodlands
- Charming Two bedroom house near Beaches and Tampa Bay attractions.
- Shore Drive Sunshine fully furnished home pet friendly
- NEW- 2 bed/2 bath WATERVIEW CENTRAL LOCATION TAMPA
- Cozy 2BR condo w/Pool in Gated community. close to beaches/resturants/shopping
- Near Clearwater Tampa Serene 3-bedroom house with Hot Tub in charming Oldsmar
- Waterfront Pool Retreat - WFH Ready - Near Corp HQs
- Experience Timeless Mid-Century Comfort Near Oldsmar’s Best Attractions
2. How many vacation rentals have private pools in Oldsmar?
There are 6 vacation rentals with private pools near Oldsmar. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Oldsmar are best for families?
If you are looking for a family-friendly vacation home in Oldsmar, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oldsmar:
4. How many Rentbyowner vacation rentals are available in Oldsmar?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 113 in the Oldsmar area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oldsmar.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand the terms and any potential fees involved.
6. Are there any house rules or restrictions I should be aware of before booking?
Yes, each vacation rental will have its own set of house rules and restrictions. You can find these details within the listing description or by reaching out to the property owner for clarification.
7. How do I confirm the availability of a vacation rental here?
Availability can be checked through the booking platform by selecting your desired dates. For more precise information or special requests, contacting the host directly is recommended.
8. Is it possible to get a detailed description or additional photos of the property before booking?
Most listings include comprehensive descriptions and multiple photos. If you need further information or specific images, it's best to contact the owner to ensure the property meets your expectations.
9. What amenities are typically included in vacation rentals in this region?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. To confirm specific amenities offered, review the listing details or ask the property owner directly.
Oldsmar Top Rated Vacation Rentals
Condo
9.8(130 Reviews)
2 Bedrooms
2 Baths
4 Guests
930 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $239/Night
7 Nights - AU $1,671
Condo
9.6(73 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $174/Night
7 Nights - AU $1,219
Hotel
9.2(1004 Reviews)
1 Bath
- Hot Tub
- Pool
- Breakfast
- Kitchen
AU $149/Night
7 Nights - AU $1,046
House
9.2(15 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $346/Night
7 Nights - AU $2,422
Hotel
8.8(936 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $167/Night
7 Nights - AU $1,172
Hotel
8.8(352 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $210/Night
7 Nights - AU $1,472
Hotel
8.4(1005 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $128/Night
7 Nights - AU $899
Hotel
8.3(51 Reviews)
4 Baths
566.45 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $281/Night
7 Nights - AU $1,970
