
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.

Davenport Dream Suite
This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Small computer table. Nearby Places: TPA Airport 12 miles, 15 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”
Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

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

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.

The Oak
Enjoy a comfortable stay in our well-appointed guest suite, featuring a kitchen, dining area, spacious master bedroom with a king-size bed, and a full bathroom that includes a Smart TV and fast Wi-Fi for your convenience. Families traveling with little ones, we provide a Pack ’n Play (for children up to 2yr) upon request, along with a high chair and a formula warmer. Free parking spot on the left side of the driveway. Suite private entrance opens to a small, peaceful and relaxing patio

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Romantic Getaway*FREE Decor AnyOcassion*Relax Bath
A cozy place to have your vacation in Tampa, private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more! Contact us with your ideas and we'll make this trip unforgettable! Located in a central area of Tampa, close to Bush Garden/Adventure Island, Raymond James Stadium,Tampa International Airport,Ybor City,Downtown Tampa,Clearwater Beach and more! Peaceful and centrally-located place to enjoy as a couple to your liking.

A&A Suite Near Tampa International Airport
A&A, the place to arrive on time for your flight. If you are traveling by plane for business, vacation or personal matters, A&A suite allows you to be 4.1 miles from the TPA. The comfortable, spacious room, with private bathroom, independent access and free parking, workplace, Wi-Fi. Strategic location to explore Skyway Park with tennis courts and playground. Golf fan? Visit Rocky Point Golf Course and Cypres Point Park, to enjoy the beach and a sunset.

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

Northdale Apartment
Welcome to our home. This accommodation is located in a quiet neighborhood, 15 minutes from airport, 30 minutes from Clearwater beach, 10 minutes from the stadium and bush garden 5 minutes from CitrusPark Mall, close to expressway Veterans and has many grocery stores nearby. It also has parking and a private entrance.

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.

Private Suite with King Bed in Safety Harbor
Guest suite unit with private king bed. Located in Safety Harbor nearby downtown with close access to shops, restaurants, and more. Features a beautiful patio area to watch the sunset or sunrise with a waterfront view. The suite features high quality furniture, bedding, and appliances.
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar

The Enchanted Lodge

Sunny Oasis: Villa Retreat

Modern and Comfortable One Bedroom Studio

Cozy Private 2BR FL condo

Cozy 3/2 residential with free parking on premises

Tiny House Oasis | Best Location | Outdoor Shower

Modern2-Story Home -Perfect for Family & Business!

Sunrise Suite -TPA, Tampa trails, Parks, Stadiums
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,767 ZAR | R3,008 ZAR | R2,992 ZAR | R2,638 ZAR | R2,574 ZAR | R2,493 ZAR | R2,493 ZAR | R2,654 ZAR | R2,381 ZAR | R2,525 ZAR | R2,654 ZAR | R2,686 ZAR |
| 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
Where should I stay in Oldsmar?
Make yourself at home in Oldsmar by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in East Lake Woodlands, over 580 vacation rentals in The Grove Of Laforest, and over 580 vacation rentals in Oldsmar.
Are there pet-friendly vacation rentals in Oldsmar?
Four-legged friends are welcome in Oldsmar. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oldsmar?
Yes! Work meets play with ease at over 80 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Oldsmar vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oldsmar have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oldsmar have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Oldsmar have wifi?
Absolutely! We offer over 20 hotel rentals with wifi in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Oldsmar have a gym?
Absolutely! We offer over 20 hotel rentals with a gym in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Oldsmar?
Experience the best of Oldsmar with our hotel rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly hotel rentals in Oldsmar?
Oldsmar has more than 10 family-friendly hotel rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Oldsmar

Total vacation rentals
Explore 150 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at R322 ZAR per night before taxes and fees

Verified guest reviews
Over 3,920 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
90 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
140 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
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Rentals with a fire pit Oldsmar
- Fitness-friendly rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with a washer and dryer Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a patio Oldsmar
- Waterfront rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with pools Oldsmar
- House rentals Oldsmar
- Family-friendly rentals Oldsmar
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Busch Gardens
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club
- Fred Howard Park




