
Holiday rentals in Oldsmar
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Top-rated holiday rentals in Oldsmar
Guests agree: these stays are highly rated for location, cleanliness and more.

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

Villa Isabella
This is a relaxing place for a couple, a clean, organized, and cozy place for work or vacation. If you want to enjoy the sunshine state, you are more than welcome to come and visit us. The place is private and has its own entrance where guests could get in and out at their own convenience. The entrance door has a smart lock, the code, and the check-in instructions will be given on the same day two hours before the check-in. The check-in will be at 3 pm and the check-out at 11 am.

cozy small apartment in the middle of tampa
Centrally located in the heart of Tampa Fl. This apartment has been recently renovated with WIFI, TV and Netflix included in the Bedroom. The apartment is just 10 minutes from Tampa International Airport, 10 minutes from the Tampa bucs Stadium, 12 minutes from Downtown Tampa, 10 minutes from Busch Gardens Tampa Bay, 10 minutes from the Zoo and just 35 minutes from Clearwater Beach and so much more ! You will love staying minutes from finest restaurants Tampa Bay has to offer.

Soothing Breeze
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. 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’

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

Apart Citrus 15 min from Airport/20 min BushGarden
The apartment is located in the community of Carrollwood Meadows, the neighborhood is quiet and peaceful. 5 minutes from Citrus Park Mall, Chili’s Grill and Bar, Olive Garden, and other restaurants 15 minutes from the Airport of Tampa and Raymond James Stadium 20 minutes from Bush Garden Parks and Recreation. 40 minutes from Clearwater Beach 20 minutes from Downtown Tampa

New York
Take a break at this unique and tranquil getaway. This is a romantic place with all that you need to surprise your partner, all you have to do is to bring your bottle of wine. It is very central and near everything, including Tampa international airport, the beach 🏖 , Bush garden and many others. Just book this beautiful suite and you won’t regret for sure.

Tiny House Oasis | Best Location | Outdoor Shower
Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor literally around the corner from Main Street. This light, private and airy gem comes completely equipped to hang out for a while. See what all the tiny home excitement is about! Now with new AC mini split for quieter and more comfortable air.

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.

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.

Cozy guest suite in Tampa.
Disfruta de la modernidad y tranquilidad de esta singular suite de invitados. Ideal localización para disfrute de los atractivos en el área de Tampa Bay (DOWNTOWN TAMPA & IBORT CITY & RAYMOND JAMES & BEACHES & BUSH GARDEN PARKS & CITRUS PARK TOWN CENTER).
Popular amenities for Oldsmar holiday rentals
Other great holiday rentals in Oldsmar

"Sweet Harbor Cottage" Walk to Downtown

Sandcastle Cottage close to beach and trail.

Seaside Charm House

Sea Side Artisan Apartment 1

Game Room + Fire Pit Fun! • 2BR • 7 mi to Beach

Palm Harbor Retreat | 2BR/2BA Near Gulf Coast Fun

The Palace 2.0

Luxury Modern Apartment A near Beachs and Airport
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $219 SGD | $238 SGD | $236 SGD | $208 SGD | $203 SGD | $197 SGD | $197 SGD | $210 SGD | $188 SGD | $222 SGD | $207 SGD | $208 SGD |
| 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 holiday rentals in Oldsmar

Total holiday rentals
Explore 150 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 3,920 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Holiday rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 of Oldsmar holiday 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!
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- Rentals with a washing machine and dryer Oldsmar
- Rentals with pools Oldsmar
- House rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a firepit Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- Fitness-friendly rentals Oldsmar
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- Hotel rooms Oldsmar
- Rentals with a fireplace Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with a hot tub Oldsmar
- Anna Maria Island
- Raymond James Stadium
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- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
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- The Don CeSar
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- Fred Howard Park




