
House holiday rentals in Oldsmar
Find and book unique houses on Airbnb
Top-rated house rentals in Oldsmar
Guests agree: these houses are highly rated for location, cleanliness and more.

Clearwater House!Near the beach!Newly renovated!
Enjoy your stay in this newly renovated home centrally located in the heart of Clearwater and the Tampa Bay Area! Family vacation, work conference, friends vacation, exploring Florida? Look no further! The home has everything you need for the perfect getaway including luxurious bedding to the max! Everything you need is within arms reach. #1 Beach in the country CLEARWATER BEACH only 20 min drive, TPA Airport 20 min away, charming Dunedin Downtown 15 min away and many more places to visit!

Barefoot Parrot /Walk DT & Waterfront/Private Yard
Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches such as Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to an unforgettable stay.

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.

Watch the Sunrise at Sunrise! @ Clearwater home.
Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

Peaceful Pet friendly 2 BR cottage with hot tub.
Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today and experience the tranquility of country living!

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

Ultimate Getaway: w/ Pool, Patio, Pool Table & BBQ
Discover your next ultimate retreat in Tampa. Lounge on leather sofas in the living room, your entertainment hub with a 65” HDTV & pool table. Step outside to a private backyard oasis, complete with a refreshing pool shining in the sun. Grill up delights on the BBQ, challenge friends to a lively game of Foosball, or test your aim in a game of cornhole. ✔ Private Pool and Spa ✔ Pool Table ✔ Cornhole Pool/Spa heating is $25/day

Charming House 2B/2B Centrally Located Tampa Bay
Come and enjoy our house, 2Bedroom/2Bathroom with a clean full kitchen is the perfect place for your next vacation! This is an entire 1200sqft, AC, dryer/ washer, huge parking space, Smart TVs, internet/Wi-Fi, First AID and closet spaces. It fits up to 6 adults. This premium location offers small driving distance to restaurants and Super Walmart, is about 3 minutes to Westfield Citrus Park Mall. Busch Gardens (9 miles away).

Lakefront Paradise with Heated Saltwater Pool
Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!

Pelican House: Game Room, Pool, 5 min to Beaches!
Your Tropical Oasis Awaits at the Florida Pelican House! Relax in our private, heated pool or take a 5-minute drive to the beautiful white sands of Sunset Beach. This fully renovated 3BR/2BA home is designed for families and groups seeking a 5-star experience with the comfort of a private retreat.
Popular amenities for house rentals in Oldsmar
House rentals with a pool

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Dunedin 5 STAR+ Heated Pool+Near Beach

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Clearwater Calling in North Clearwater Beach

Tropical Oasis Retreat w/ Heated Pool

Walk to Raymond James Stadium! Pool/ Hot Tub Home!

Lakeview Retreat with Private Pool Perfect Getaway

Coastal Escape: heated saltwater pool & playground
Weekly house rentals

Clearwater Getaway off the Gulf Coast

Clearwater Lake House

Balay Clearwater: Heated Pool, Grill, 15 min Beach

Remodeled 4 BR 2 bath w/spa near beach & ball park

Peaceful Lakefront Home!

Florida Retro AIRBnB

Peaceful Hideaway

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes
Private house rentals

Clearwater peaceful retreat -PETS Fenced Backyard

Best House on the Trail

Central Clearwater | 3BR Modern Retreat

Palm Harbor Renovated Hideaway!

Clearwater Cottage # 2

Beachhouse Inspired Villa Close Honeymoon Island

Cozy place for your enjoyment

8 min from Aiport-POOL SaL-bookfewerdayswritetome
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £145 | £158 | £149 | £133 | £126 | £124 | £131 | £131 | £126 | £136 | £142 | £139 |
| 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 |
Quick stats about house rentals in Oldsmar

Total holiday rentals
Explore 90 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 2,860 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Oldsmar holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool 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 a firepit Oldsmar
- Rentals with a patio Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with pools Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with beach access Oldsmar
- Pet-friendly rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with outdoor seating Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a fireplace Oldsmar
- House rentals Pinellas County
- House rentals Florida
- House rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
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- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Tampa Convention Center
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- Lakewood National Golf Club
- The Don CeSar




