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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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, 164 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 favorite
A serene outdoor seating area features white adirondack chairs positioned on a natural stone patio, surrounded by lush green foliage and tropical plants. A glimpse of a swimming pool can be seen in the background, framed by additional seating and vibrant landscaping.
Apartment in Dunedin
4.94 out of 5 average rating, 122 reviews

Island Oak

This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

Guest favorite
A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.
Home in Palm Harbor
4.95 out of 5 average rating, 164 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!

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
4.71 out of 5 average rating, 110 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.

Top guest favorite
A spacious cabin is gently illuminated by string lights, creating a warm glow against the evening sky. Surrounding the home are trees and a hammock, with a grassy area leading up to the porch where seating is visible.
Farm stay in Odessa
4.99 out of 5 average rating, 338 reviews

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Top guest favorite
A tiny house, characterized by its vibrant green exterior and metal roof, is positioned alongside a gently sloping ramp leading to the entrance. Surrounding foliage and gravel pathways offer a natural setting, while the background displays open fields and a fading sunset.
Tiny home in Wesley Chapel
4.97 out of 5 average rating, 162 reviews

King Lake Hideaway

Experience something different Our Tiny house with the amenities of home. Enjoy our very private spot in nature. Beautiful lake view. This is a tiny house. 280 sq feet including the loft. Lots of natural light. It’s perfect for relaxing. We are close to beaches, Sporting venues, museums the aquarium and Busch Gardens in Tampa. Situated between Epperson and Mirada lagoons. Wesley Chapel has movie theaters, mini golf, shopping and restaurants within a short drive.

Guest favorite
Home in Palm Harbor
4.95 out of 5 average rating, 189 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and three TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

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, 154 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 comfortable living area features a gray sectional sofa adorned with decorative pillows, paired with a cozy armchair. A glass coffee table sits on a patterned area rug, with a potted plant adding a touch of greenery. Natural light is visible from an adjacent room.
Apartment in Dunedin
4.98 out of 5 average rating, 102 reviews

In Downtown-Porch-Parking-603Mbps-Kitchen

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. First floor 2 bedroom apartment is tastefully decorated, clean and ready for your stay! Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more, or just relax and watch the action from the front porch.

Superhost
A private entrance is visible, featuring a clean white gate that leads into the apartment area. A paved walkway of gray stones is bordered by white gravel and greenery, creating an inviting access point. Nearby structures can be seen, emphasizing the neighborhood's quiet environment.
Apartment in Tampa
4.84 out of 5 average rating, 181 reviews

Private apartment perfectly located in Citrus park

A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

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, 309 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 light-colored cottage exterior is presented, featuring a welcoming front staircase with wooden steps. Decorative wreaths adorn the front door, complemented by potted plants hanging on either side. Lush greenery surrounds the property, enhancing the outdoor setting.
Cottage in Dunedin
4.96 out of 5 average rating, 142 reviews

BeachBunkies Cottage 2. 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.

Popular amenities for Oldsmar vacation 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 70 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 90 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Oldsmar?

    Oldsmar has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Oldsmar with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Oldsmar have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oldsmar have wifi?

    Absolutely! We offer over 90 house rentals with wifi in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • 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 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.

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 € 17 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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