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Vacation rentals in Oldsmar

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Top-rated vacation rentals in Oldsmar

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

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Guest favorite
A vibrant sunset paints the sky in warm hues of orange and yellow, as the sun sinks below the horizon over a tranquil ocean. The image conveys a serene coastal atmosphere, resonating with the proximity to nearby beaches.
Guesthouse in Clearwater
4.9 out of 5 average rating, 432 reviews

Minutes to Beaches w/King Bed Private Updated

This private home away from home near pristine beaches sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

Top guest favorite
Guest suite in Tampa
4.96 out of 5 average rating, 255 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 favorite
Two bright yellow chairs are positioned on a grassy area, overlooking a serene lake. The tranquil water reflects surrounding greenery and features a decorative flamingo. A peaceful atmosphere is created by the nearby trees and open space.
Guest suite in Logan Gate Village
4.99 out of 5 average rating, 188 reviews

Monterey Suite at Citrus Park

You will enjoy a sparkly clean Studio Suite with a private patio area and a peaceful lake view, comfortable adjustable queen bed, full bathroom, cute kitchen and computer station with high speed internet. Conveniently located ,14 minutes to airport/toll , walking distance to Super Walmart. Minutes to Citrus Park Mall , AMC Theaters , Publix, Costco, Sprouts, Airport, Busch Gardens, Raymond James Stadium, NY Yankees Training Camp, Upper Tampa Bay Trail were you can rent bikes and many more.

Top guest favorite
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.
Guesthouse in Dunedin
4.82 out of 5 average rating, 139 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 favorite
Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.
Cottage in Tampa
4.98 out of 5 average rating, 243 reviews

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.

Top guest favorite
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 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, 147 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
A modern living space features a comfortable blue sofa adorned with decorative cushions. A sleek coffee table with a candle sits in front. The open kitchen showcases contemporary cabinetry and a kitchen island with bar seating. Light fixtures illuminate the area, enhancing the inviting ambiance.
Guesthouse in Safety Harbor
4.98 out of 5 average rating, 109 reviews

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!

Top guest favorite
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 favorite
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, 122 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 favorite
A spacious studio features a comfortable bed adorned with a patterned blanket. Soft lighting is provided by bedside lamps and a floor lamp. Blue curtains frame the sliding glass door, which leads to a small outdoor seating area. A modern dresser and ceiling fan enhance the relaxing ambiance.
Home in Tampa
4.97 out of 5 average rating, 453 reviews

Private Studio-1 Exquisite space/King Bed/Near TPA

Enjoy your stay in Tampa in this cozy, newly remodeled studio! This studio is located at the center of Town and Country and is a short drive from Tampa International Airport (7 miles, which is 14 minutes away from the studio).

Popular amenities for Oldsmar vacation rentals

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$35,983 GYDG$39,121 GYDG$38,912 GYDG$34,309 GYDG$33,472 GYDG$32,426 GYDG$32,426 GYDG$34,518 GYDG$30,962 GYDG$36,610 GYDG$34,100 GYDG$34,309 GYD
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 vacation rentals in Oldsmar

  • Total vacation rentals

    Explore 150 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Oldsmar vacation rentals include wi-fi 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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