Vacation rentals in Oldsmar

Modern Private Estate | Central to Tampa & Beaches

Experience this 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, & guests who value tranquility, and a thoughtful design!

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

Cottage in Paradise.

Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

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.

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.

Oldsmar Oasis

Enjoy a peaceful stay in this 2 bed, 2 bath condo in quiet, gated East Lake Woodlands Neighborhood. Features a king bed and bunk beds—perfect for families. Relax by the community pool or unwind after a day exploring. Conveniently located off Tampa Rd, just minutes from shopping, dining, a movie theater, and Tampa Bay Downs. Only 20 minutes from the Tampa International Airport. Ideal for short getaways or extended stays with all the comforts of home.

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

beautiful home oldsmar near to the beach

This is a beautiful and spacious home, located in Oldsmar, Pinellas County , Florida. It is perfect for family vacation or romantic getway, it is single family home with 3 bedrooms 2 bathrooms 2 car garage . it is minutes driving to the beaches , shopping and entertainment, walking distance to fine restaurants but still tucked way so very quiet, the neiborghood is very friedly and safe !

Tiny House Oasis - 2 Min Walk to Main Street

Experience unique tiny home living in the heart of downtown Safety Harbor! This stylish 132 sq. ft. retreat for two features soaring ceilings and a large, private outdoor oasis with a firepit and a one-of-a-kind outdoor shower. Just steps from Main Street's shops, restaurants, and the beautiful waterfront pier. Perfect for a memorable, walkable getaway.