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Holiday rentals in Oldsmar

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oldsmar

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

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Top guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.98 out of 5 average rating, 161 reviews

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

Top guest favourite
A cozy sleeping area features a wooden headboard and a red bedspread on a spacious bed. Two nightstands with lamps flank the bed, while decorative wall plates are displayed above. A sliding mirror closet door is visible on one side of the room.
Guest suite in Tampa
4.95 out of 5 average rating, 305 reviews

Villa Isabella

This is a relaxing place for a couple, a clean, organized, and cozy place for work or vacation. If you want to enjoy the sunshine state, you are more than welcome to come and visit us. The place is private and has its own entrance where guests could get in and out at their own convenience. The entrance door has a smart lock, the code, and the check-in instructions will be given on the same day two hours before the check-in. The check-in will be at 3 pm and the check-out at 11 am.

Guest favourite
Flat in Tampa
4.91 out of 5 average rating, 359 reviews

cozy small apartment in the middle of tampa

Centrally located in the heart of Tampa Fl. This apartment has been recently renovated with WIFI, TV and Netflix included in the Bedroom. The apartment is just 10 minutes from Tampa International Airport, 10 minutes from the Tampa bucs Stadium, 12 minutes from Downtown Tampa, 10 minutes from Busch Gardens Tampa Bay, 10 minutes from the Zoo and just 35 minutes from Clearwater Beach and so much more ! You will love staying minutes from finest restaurants Tampa Bay has to offer.

Top guest favourite
A combined living and sleeping area is shown, featuring a spacious bed with a black and white plaid coverlet. A kitchenette with modern appliances is visible, alongside a small dining space accommodating two stools. A futon, designed for ample seating, is situated to the side.
Guest suite in Tampa
4.96 out of 5 average rating, 274 reviews

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’

Top guest favourite
Guest suite in Tampa
4.95 out of 5 average rating, 223 reviews

A&A Suite Near Tampa International Airport

A&A, the place to arrive on time for your flight. If you are traveling by plane for business, vacation or personal matters, A&A suite allows you to be 4.1 miles from the TPA. The comfortable, spacious room, with private bathroom, independent access and free parking, workplace, Wi-Fi. Strategic location to explore Skyway Park with tennis courts and playground. Golf fan? Visit Rocky Point Golf Course and Cypres Point Park, to enjoy the beach and a sunset.

Top guest favourite
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, 148 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

Guest favourite
An outdoor seating area features two black woven chairs and a glass-top table, shaded by a large umbrella. A clean white fence provides privacy, while small white stones cover the ground, creating a neat appearance. A door leads into the guesthouse interior.
Flat in Tampa
4.77 out of 5 average rating, 271 reviews

Apart Citrus 15 min from Airport/20 min BushGarden

The apartment is located in the community of Carrollwood Meadows, the neighborhood is quiet and peaceful. 5 minutes from Citrus Park Mall, Chili’s Grill and Bar, Olive Garden, and other restaurants 15 minutes from the Airport of Tampa and Raymond James Stadium 20 minutes from Bush Garden Parks and Recreation. 40 minutes from Clearwater Beach 20 minutes from Downtown Tampa

Superhost
A modern sleeping area features a spacious bed with soft linens and a light pink throw blanket. A flat-screen TV is mounted on the wall, and natural light enters through a window with blinds. A contemporary glass railing separates the space from a staircase.
Guest suite in Tampa
4.79 out of 5 average rating, 346 reviews

New York

Take a break at this unique and tranquil getaway. This is a romantic place with all that you need to surprise your partner, all you have to do is to bring your bottle of wine. It is very central and near everything, including Tampa international airport, the beach 🏖 , Bush garden and many others. Just book this beautiful suite and you won’t regret for sure.

Top guest favourite
A cozy interior space is highlighted by light wood paneling and textured wall decor. A comfortable bed with dark bedding is positioned near a wooden accent wall, featuring a mounted television. Natural light fills the room through a nearby window, enhancing the inviting atmosphere.
Guest house in Safety Harbor
4.94 out of 5 average rating, 297 reviews

Tiny House Oasis | Best Location | Outdoor Shower

Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor literally around the corner from Main Street. This light, private and airy gem comes completely equipped to hang out for a while. See what all the tiny home excitement is about! Now with new AC mini split for quieter and more comfortable air.

Top guest favourite
The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.
Cottage in Oldsmar
4.96 out of 5 average rating, 307 reviews

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.

Guest favourite
A charming cottage exterior is framed by lush greenery and palm trees, with a welcoming blue front door. A stone pathway leads to the entrance, surrounded by an inviting garden. The cottage is nestled within a fenced yard, providing a sense of privacy.
Home in Dunedin
4.89 out of 5 average rating, 123 reviews

BeachBunkies Cottage 1. Four miles to the beach!

Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.

Top guest favourite
A modern bedroom features a spacious bed with a light blue quilt, complemented by two bedside lamps providing soft illumination. A decorative painting hangs above the headboard, and a small tray rests on the bed with seasonal touches. Neutral tones create a serene atmosphere.
Guest suite in Logan Gate Village
4.98 out of 5 average rating, 122 reviews

Cozy guest suite in Tampa.

Disfruta de la modernidad y tranquilidad de esta singular suite de invitados. Ideal localización para disfrute de los atractivos en el área de Tampa Bay (DOWNTOWN TAMPA & IBORT CITY & RAYMOND JAMES & BEACHES & BUSH GARDEN PARKS & CITRUS PARK TOWN CENTER).

Popular amenities for Oldsmar holiday rentals

When is the best time to visit Oldsmar?

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Avg. price$219 SGD$238 SGD$236 SGD$208 SGD$203 SGD$197 SGD$197 SGD$210 SGD$188 SGD$222 SGD$207 SGD$208 SGD
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

Frequently Asked Questions

  • Where should I stay in Oldsmar?

    Make yourself at home in Oldsmar by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in East Lake Woodlands, over 580 vacation rentals in The Grove Of Laforest, and over 580 vacation rentals in Oldsmar.

  • Are there pet-friendly vacation rentals in Oldsmar?

    Four-legged friends are welcome in Oldsmar. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oldsmar?

    Yes! Work meets play with ease at over 80 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Oldsmar vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Oldsmar have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oldsmar have air conditioning?

    Absolutely! We offer over 80 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Oldsmar have wifi?

    Absolutely! We offer over 20 hotel rentals with wifi in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Oldsmar have a gym?

    Absolutely! We offer over 20 hotel rentals with a gym in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in hotel rentals in Oldsmar?

    Experience the best of Oldsmar with our hotel rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly hotel rentals in Oldsmar?

    Oldsmar has more than 10 family-friendly hotel rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Oldsmar

  • Total holiday rentals

    Explore 150 holiday rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    140 of Oldsmar holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oldsmar rentals

  • 4.8 Average rating

    Oldsmar stays are highly rated by guests – averaging 4.8 out of 5!

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