Holiday houses in Oldsmar

Cozy 3/2 residential with free parking on premises

Welcome to stunning 3/2/2 home. Your family will be close to everything when staying at this centrally-located place. It's .3 mile to R.E. Olds Park, 1.5 mile to Mobbly Bayou Beach Park, 12 miles to TPA Airport, 15 miles to Clearwater Beach, 17 miles to Tampa Riverwalk, 18 miles Busch Gardens, 24 miles to St. Peterburg Beach. Long for Dim Sum while you're in Tampa: 13 miles Yummy House South China Bistro! Or Vietnamese food: 7 miles Thinh An Kitchen & Tofu, 11 miles SaiGon Deli & SGMarket.

Sunny Oasis: Villa Retreat

Welcome to a stunning 2-bedroom, 2-bathroom villa nestled in the heart of sunny Florida! Whether you're seeking a relaxing beach getaway or exploring all that Florida has to offer, this villa is your perfect destination. Located 15-20 minutes from the beach in a prime location, you'll find a plethora of dining, shopping, and entertainment options nearby, ensuring there's something for everyone to enjoy. Book your stay today and experience the ultimate in comfort, convenience, and coastal charm.

Cozy Private 2BR FL condo

Experience ultimate relaxation in this perfectly located private home away from home. Relax on your enclosed lanai overlooking your wooded backdrop. Second floor condo with vaulted ceilings in pristine condition and complete with all furnishings & living essentials! Community Pool And close to Westfield Countryside Mall, area shopping, restaurants, public golf courses, entertainment, plus the sandy beaches of Honeymoon Island or Clearwater. located in the gated community-East Lake woodlands

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

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

This 2 bed 2 bath condo is located in a quiet peaceful golf course neighborhood yet minutes from shopping & AMC theatre! Enjoy amazing sunsets and wonderful water view of large pond from the spacious balcony. Pool is just steps away from condo. Honeymoon Island Park 8 miles, beaches 16 miles. Enjoy your stay w/ complimentary wifi & many other amenities! Please let us know how to make your stay as comfortable as possible. Message w/ any questions we may be able to accommodate shorter stays.

Modern2-Story Home -Perfect for Family & Business!

This two-story house features 4 comfortable bedrooms, 3.5 bathrooms, a modern, fully equipped kitchen, and a relaxing patio with a BBQ grill—perfect for family gatherings or group getaways. Located in a peaceful and beautiful neighborhood, you’ll enjoy the quiet surroundings while being just 20 minutes from the airport and a major shopping mall, R.E. Park is just a 10-minute walk away. Whether you’re visiting for vacation or work, this home offers both comfort and convenience for your stay.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Modern Private Estate | Central to Tampa & Beaches

Experience a private 1-acre modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, and guests who value quiet and thoughtful design!

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.

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

Luxe Apartment | Water Views | Covered Balcony

Upscale, comfortable suite located within central Safety Harbor. This beautiful apartment is great for a quick getaway or a longer vacation rental. Located steps away from Bayshore Blvd which borders Tampa Bay and a 10-minute walk to Main Street Safety Harbor. Beautifully professionally designed contemporary and comfy décor. Easily walk to many restaurants, breweries, and shops!

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.