Holiday rentals in Oldsmar

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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
Guest suite in Tampa
4.96 out of 5 average rating, 258 reviews

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

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

Superhost
An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.
Guest house in Dunedin
4.82 out of 5 average rating, 140 reviews

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.

Top guest favourite
A spacious sleeping area features a modern white bed dressed in a black coverlet, complemented by matching throw pillows. A sleek dresser stands nearby, and the wall behind the bed showcases a stylish wavy pattern in black and silver. A small seating area with two chairs is visible.
Guest house in Tampa
4.97 out of 5 average rating, 326 reviews

Romantic Getaway*FREE Decor AnyOcassion*Relax Bath

A cozy place to have your vacation in Tampa, private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more! Contact us with your ideas and we'll make this trip unforgettable! Located in a central area of Tampa, close to Bush Garden/Adventure Island, Raymond James Stadium,Tampa International Airport,Ybor City,Downtown Tampa,Clearwater Beach and more! Peaceful and centrally-located place to enjoy as a couple to your liking.

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, 276 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’

Guest favourite
A cozy sleeping area features a compact bed with a navy blue coverlet. Two rolled towels are neatly arranged on the bed. Natural light filters through two windows adorned with white blinds, and a light-colored nightstand sits beside the bed, illuminated by a small lamp.
Guest suite in Tampa
4.93 out of 5 average rating, 180 reviews

Shabby Chic Studio in West Tampa.

This private studio is located in the West Tampa area next to Raymond James Buccaneer Stadium. Very close to downtown, Midtown, Tampa airport, International plaza , the interstate, and to popular restaurants such as Flemings, Ocean Prime and Armature works. It comfortably accommodates up to 2 people. This shabby chic hideaway is ideal for touristic or work/study related trips. Every detail has been well-thought and curated to deliver the best experience for our guests.

Top guest favourite
Guest suite in Tampa
4.95 out of 5 average rating, 225 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, 149 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 favourite
A view from the entryway opens to a private patio area, featuring turquoise chairs arranged around a table. A doormat with a wine glass design is positioned at the threshold, welcoming guests into the space. Natural light brightens the entrance.
Guest house in Tampa
4.91 out of 5 average rating, 107 reviews

Relax in the tampa bay area #1

I invite you to spend your vacation, a romantic getaway or simply a work stay in this accommodation decorated and equipped with everything you may need to just relax and enjoy. It is conveniently located: Tampa International Airport: 3.5 miles Bush Gardens: 15 miles. Clearwater Beach: 20 miles. International Plaza and Bay Street: 4.3 miles Raymond James Stadium: 6 miles.

Top guest favourite
A well-appointed bedroom features a spacious bed with crisp white sheets and a contemporary headboard. Nightstands with lamps are positioned on either side, while a large artwork piece hangs above the bed. The room's floor is adorned with elegant marble tiles, enhancing the overall aesthetic.
Flat in Tampa
4.99 out of 5 average rating, 352 reviews

Northdale Apartment

Welcome to our home. This accommodation is located in a quiet neighborhood, 15 minutes from airport, 30 minutes from Clearwater beach, 10 minutes from the stadium and bush garden 5 minutes from CitrusPark Mall, close to expressway Veterans and has many grocery stores nearby. It also has parking and a private entrance.

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 cozy bedroom is highlighted by a spacious bed covered with a soft throw. Mirrored closet doors reflect natural light, while a wooden desk and chair offer a functional workspace. A ceiling fan and flat-screen TV enhance the comfort of the space.
Guest suite in Timberlane Woodlake
4.92 out of 5 average rating, 138 reviews

Cozy Red Door Studio

Keep it simple at this peaceful and centrally located place. Very cozy and private with a carport parking spot. Close to beaches, shopping, Tampa International Airport, Busch Gardens and more!

Popular amenities for Oldsmar holiday rentals

When is the best time to visit Oldsmar?

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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 € 17 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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