House vacation rentals in Oldsmar

Find and book unique houses on Airbnb

Top-rated house rentals in Oldsmar

Guests agree: these houses are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.
Home in Barrington Hills
4.92 out of 5 average rating, 271 reviews

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.

Top guest favorite
A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.
Home in Palm Harbor
5 out of 5 average rating, 122 reviews

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

Superhost
A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.
Home in Tampa Heights
4.9 out of 5 average rating, 248 reviews

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).

Guest favorite
A screened-in pool area is featured, with a sparkling swimming pool shaped to enhance relaxation. Comfortable seating is arranged nearby, including lounge chairs and a shaded area. The inviting water reflects the blue sky above, with tropical plants adding a touch of greenery to the space.
Home in Safety Harbor
4.9 out of 5 average rating, 105 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

Top guest favorite
A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.
Home in Palm Harbor
4.99 out of 5 average rating, 143 reviews

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

Guest favorite
A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.
Home in Oldsmar
4.7 out of 5 average rating, 108 reviews

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.

Guest favorite
The exterior of a two-story home is featured, set in a lush, green environment near a tranquil lagoon. Tall trees and hanging moss frame the structure, which is elevated slightly above the water. The calm water reflects the house and surrounding foliage.
Home in Tarpon Springs
4.94 out of 5 average rating, 233 reviews

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.

Top guest favorite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 146 reviews

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

Top guest favorite
The living area features a spacious layout with a comfortable gray sofa and a decorative wooden coffee table. A flat-screen TV is mounted on the wall, while a well-equipped kitchen with modern fixtures is visible in the back. Natural light enters through the windows, creating a bright atmosphere.
Home in Tampa
4.97 out of 5 average rating, 117 reviews

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).

Guest favorite
A modern living area showcases a sleek gray couch featuring soft tufting and a white decorative pillow. A circular wooden coffee table, supported by a geometric metal base, rests nearby, providing a casual yet stylish touch to the space.
Home in Allen's Ridge
4.89 out of 5 average rating, 218 reviews

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.

Top guest favorite
A charming guest house exterior is framed by vibrant flowering shrubs. The structure features a covered porch with a small table and chairs. Nearby, bicycles are lined against the wall, complementing the inviting atmosphere of the shared outdoor space.
Home in Clearwater
4.96 out of 5 average rating, 390 reviews

Coastal Cottage E - Beach items and Bikes!

30 day minimum - This guest house has been fully remodeled with brand new mini split-air conditioners. It shares a parking lot, grill, and laundry with other units. Included with this unit are 4 beach cruiser bikes, beach chairs, beach towels, umbrellas, coolers beach bag, bag of sand toys, beach cart, and more! Note: sorry no animals 💕🙏

Guest favorite
A work area is positioned near a window, featuring a sleek desk and an adjustable white chair. Light gray curtains frame the window, allowing for natural light. A small lamp and decorative item are placed on the desk, contributing to the space's functional design.
Home in Tampa
4.85 out of 5 average rating, 132 reviews

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.

Popular amenities for Oldsmar house rentals

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$40,599 GYDG$44,156 GYDG$41,645 GYDG$37,251 GYDG$35,158 GYDG$34,530 GYDG$39,762 GYDG$36,623 GYDG$36,623 GYDG$37,669 GYDG$38,088 GYDG$37,669 GYD
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

Quick stats about house rentals in Oldsmar

  • Total vacation rentals

    Explore 80 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at G$6,278 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,780 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Oldsmar vacation 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Oldsmar
  6. House rentals