Holiday rentals in Oldsmar

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

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.

Luxury Modern Retreat I Spacious, Private & Serene

Welcome to Bayside Breeze! A serene getaway just 11 miles from Tampa Airport, 20 miles to Clearwater Beach, and 25 miles to St. Pete. This modern, designer-renovated home features a stylish interior, chef’s kitchen, spacious bedrooms, a huge bonus room, and a four-car garage. Nestled on a lush acre with palms, oaks, and a koi pond, it also offers ample space for RV and boat parking. Perfect for relaxing or exploring top Florida attractions. Ideal for corporate stays and relocating families!

Soothing Breeze

This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Nearby Places: TPA Airport 12 miles, 15 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

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.

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.