
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.

Lakefront home near beaches w/ waterview, pets ok
Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8
Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, 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 this beloved Dunedin favorite!

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.

New Prime location Riverwalk Luxe 3BR 3BA
Tampa's newest 3BR 3BA gem: Aster Haus, just 4-streets over from the Riverwalk & Armature Works. Primary King en-suite bedroom boasts private balcony for two; living area, a grand 25ft ceiling. Outdoors, a lush courtyard with covered porch, pergola & relaxing fountain beckon. Private parking for 2 cars. Modern amenities seamlessly blend with timeless bungalow charm, in this new build. Enjoy the prime walkable Tampa Heights location to access the Tampa’s finest.

Rooms with a Pool
Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

A perfect Lake House get away
Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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

Tarpon Lake Escape LLC
Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Private pool, Golf Cart, Completely Renovated!
Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!

Tropical Oasis Retreat w/ Heated Pool
Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

The perfect lake house getaway near the airport.
Relax with the whole family in this cozy residence in the Tampa Bay area. Enjoy the spacious backyard and unwind in the hot tub with peaceful views of the lake. Set in a centric location near the International Airport, Raymond James Stadium, Busch Gardens, Adventure Island, Citrus Park mall and Florida's best-rated beaches.
Popular amenities for Oldsmar house rentals
House rentals with a pool

House in Oldsmar near Clearwater / Tampa Hot tub*

Hot Tub, Heated Pool, 2 Master Suites, Beach

The Jungalow SOHO - Pool/Hot Tub

Sunny's Retreat

Cozy Family Retreat, Tampa: Private Pool Oasis

The Palm Haus • Heated Pool • Near Beach • Games

The T and C Club

Delightful elegant lake home
Weekly house rentals

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

Cozy Stay Near Airport, Beaches & City Attractions

CasaBella

The Coastal Calm - Entire Unit

Private Pool! Tropical Beaches! Palm Harbor, FL

WOW! Dunedin Coastal POOL Home-beaches-eateries

Gulf View on Bay: Newly Renovated

Cypress Place | Your Serene Retreat near Tampa!
Private house rentals

Safety Harbor Bird House with Lake View

Nice Sparkling Clean Home with Pool.

Heated Pool & Spa Oasis Near Clearwater Beach

Cozy Villa Close to Tampa Bay & Clearwater Beaches

Cozy Hen House Retreat

Waterfront - 6 nights for the price of 3 deal!

Coastal Cottage Near Beaches w/ Golf Cart Rental!

3/2 | Near Downtown | Dog Friendly | Park access
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $342 NZD | $366 NZD | $378 NZD | $304 NZD | $287 NZD | $282 NZD | $299 NZD | $299 NZD | $287 NZD | $311 NZD | $325 NZD | $318 NZD |
| 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 $51 NZD per night before taxes and fees

Verified guest reviews
Over 2,910 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar holiday rentals include Wi-Fi 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 fire pit Oldsmar
- Pet-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with outdoor seating Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with pools Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with a patio Oldsmar
- Family-friendly rentals Oldsmar
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- Anna Maria Island
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