
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.

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

Island Oak
This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

Tropical Getaway w/Heated Pool & King Beds
Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!

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.

Farm and lake stay at Maison de L'eau Douce
LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

King Lake Hideaway
Experience something different Our Tiny house with the amenities of home. Enjoy our very private spot in nature. Beautiful lake view. This is a tiny house. 280 sq feet including the loft. Lots of natural light. It’s perfect for relaxing. We are close to beaches, Sporting venues, museums the aquarium and Busch Gardens in Tampa. Situated between Epperson and Mirada lagoons. Wesley Chapel has movie theaters, mini golf, shopping and restaurants within a short drive.

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.

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

In Downtown-Porch-Parking-603Mbps-Kitchen
Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. First floor 2 bedroom apartment is tastefully decorated, clean and ready for your stay! Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more, or just relax and watch the action from the front porch.

Private apartment perfectly located in Citrus park
A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

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 2. 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.
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar

Lemon Drop

Sunny Oasis: Villa Retreat

Pet Friendly Pool Oasis St Pete/Gulfport

"Sweet Harbor Cottage" Walk to Downtown

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

Cheerful 2 Bedroom House _ French doors to Patio

Palm Harbor Retreat | 2BR/1BA Near Gulf Coast Fun

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 | € 149 | € 162 | € 161 | € 142 | € 138 | € 134 | € 134 | € 143 | € 128 | € 136 | € 143 | € 144 |
| 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 70 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 90 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Oldsmar?
Oldsmar has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oldsmar?
Experience the best of Oldsmar with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oldsmar have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oldsmar have wifi?
Absolutely! We offer over 90 house rentals with wifi in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
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 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.
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 € 17 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!
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