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

Wonderful family friendly home in Dunedin FL
Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

Coastal Escape: heated saltwater pool & beaches
★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Downtown Tampa Pool House! Walk to Armature Works!
Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

Tropical Oasis Retreat w/ Heated Pool
Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

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.

Tree House Treasure
We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

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

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).

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr
This stylish place featuring a heated pool upon request is perfect for groups, family vacation or work trip. Has an open layout nice kitchen all furniture and appliances brand new. We are walking distance to Lake Tarpon-Bring your boats and jet skiis! Honeymoon Island is 8.8 miles Tampa, Dunedin Causeway only 7.6 miles . Tarpon Springs sponge docks 5.8 miles .St. Pete & Clearwater beach are not to far by car.

Cute Lil' House Near Historic Downtown Palm Harbor
They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

My Little White Space .
My apartment is located an excellent position of access to different places of Tampa bay .Apartment with independent entrance.Near to: Tampa international airport-4miles Mall international plaza-4 miles Downtown Tampa 8.7 miles Raymond James stadium Beaches within 5 miles. NO CHILDREN OR PETS WILL BE ADMITTED.

Modern & Spacious Retreat with Private Pool!
Welcome to our exquisite Airbnb in Oldsmar, Florida, where luxury and convenience converge in a SINGLE-story haven. This delightful getaway promises an unforgettable stay for travelers seeking relaxation, outdoor adventures, and a touch of historical charm.
Popular amenities for house rentals in Oldsmar
House rentals with a pool

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

Heated Pool, 10 min to Beach, Close to Restaurants

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Heated & Screened in Pool-All Essentials Provided

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

Tropical Getaway w/Heated Pool & King Beds

Boaters Paradise- Waterfront Heated Pool King Beds
Weekly house rentals

Casual, relaxing 2/2 SFH remodeled, in Dunedin.

Casa Del Sole

Cozy Florida home

Palm Harbor Renovated Hideaway!

Simple pleasure. Two blocks to bay and parks.

Private pool, Golf Cart, Completely Renovated!

The memories house

2 Bed 2 Bath Remodeled House Palm Harbor
Private house rentals

Paradise by the Park

The Heaven

Sunny's Retreat

Cozy Hen House Retreat

The Palm Haus • Heated Pool • Near Beach • Games

Newly Updated & Clean Vacation Home

The Wandering Moon

Cozy & Convenient 1BR - By Beach
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 SGD | $275 SGD | $260 SGD | $232 SGD | $219 SGD | $215 SGD | $228 SGD | $228 SGD | $219 SGD | $228 SGD | $237 SGD | $235 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 |
Quick stats about house rentals in Oldsmar

Total holiday rentals
Explore 80 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 2,780 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 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 firepit Oldsmar
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- Anna Maria Island
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
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- North Beach
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