Waterfront vacation rentals in Oldsmar

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Top-rated waterfront accommodations in Oldsmar

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

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Top guest favourite
A charming cottage exterior is presented, featuring a green front door and a large screened porch. Lush landscaping, including diverse plants and flowers, frames the entrance. Spanish moss hangs from the trees, creating a tranquil outdoor atmosphere under a partly cloudy sky.
Cottage in Lutz
4.94 out of 5 average rating, 197 reviews

Little piece of Heaven 2

This 2 bedroom cozy cottage is nestled on an almost 1.5 acres piece of property on a serene spring fed lake. The cottage is a laid back coastal feel with all of the amenities of home & tucked away in between the hustle and bustle of Tampa without ever knowing it. Easy access to the Veteran's Expressway that will take you to anywhere from Clearwater and our pristine beaches to Downtown St. Pete. I275 will take you to Downtown Tampa, Busch Gardens and Adventure Island. I-4 will take you to Orlando

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
4.95 out of 5 average rating, 185 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 spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.
Place to stay in Dunedin
4.97 out of 5 average rating, 189 reviews

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

Top guest favourite
A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.
Home in Palm Harbor
4.93 out of 5 average rating, 125 reviews

Lakefront home near beaches w/ waterview, pets ok

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

Top guest favourite
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, 260 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 favourite
A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.
Condo in Tampa
4.95 out of 5 average rating, 370 reviews

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

Guest favourite
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, 247 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 favourite
A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.
Home in Odessa
4.96 out of 5 average rating, 123 reviews

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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, 163 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
The image captures a serene view of the canal with calm, reflective waters. Lush greenery lines the banks, while several boats are seen docked along the shore. Bright sunlight illuminates the scene, highlighting the tranquility of the waterfront setting.
Home in Palm Harbor
4.98 out of 5 average rating, 112 reviews

Tarpon Lake Escape LLC

Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Guest favourite
A well-appointed bathroom features a freestanding soaking tub surrounded by natural stone walls. A double vanity with modern fixtures is situated near the window, allowing for natural light. A glass-enclosed shower and stylish fixtures enhance the functional layout.
Home in Tampa
4.86 out of 5 average rating, 597 reviews

Urban River Edge Loft w/Soaking Tub and King Bed

A spacious apartment with soaring ceilings encompassing all of the upper story of a historic bungalow, just steps from the Hillsborough River. You'll have your own deck overlooking the river, and be only 10 to 15 minutes from dwntwn Tampa, Amalie Arena, Armature Works, Ray James Stadium, Busch Gardens, & Cypress Point Beach -Complimentary Kayaks Included -Fast WiFi & Smart TV -Soaking Tub -Full Kitchen -Wood Burning Firepit

Top guest favourite
A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.
Home in Tampa
4.91 out of 5 average rating, 154 reviews

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Enjoy this South Tampa waterfront pool home, centrally located off Westshore. Close proximity to Clearwater, downtown Tampa, and Orlando. Featuring brand new contemporary finishes and breathtaking views. This home Is monitored on video surveillance on the exterior corners of the home as well as the back yard and front door ring camera. Device will record during reservations. No parties of any kind will be permitted.

Popular amenities for Oldsmar waterfront rentals

When is the best time to visit Oldsmar?

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Quick stats about waterfront rentals in Oldsmar

  • Total vacation rentals

    Explore 20 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Oldsmar vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

  • 4.9 Average rating

    Oldsmar stays are highly rated by guests—averaging 4.9 out of 5!

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