Waterfront holiday rentals in Oldsmar

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Oldsmar

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

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Guest favourite

Flat in Tampa

4.88 out of 5 average rating, 173 reviews

Private 1 Bed Apt with Pool and water front.

Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

Top guest favourite

Bungalow in Oldsmar

4.98 out of 5 average rating, 124 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

Guest favourite

Home in Palm Harbor

4.92 out of 5 average rating, 116 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!

Superhost

Home in Tampa

4.77 out of 5 average rating, 265 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

Guest favourite

Cottage in Indian Shores

4.96 out of 5 average rating, 160 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Superhost

Apartment in Tampa

4.86 out of 5 average rating, 111 reviews

Mangrove Bay | Waterfront Suite w/ Bay Views

Experience the perfect blend of comfort and convenience at Tampa Bay’s all-waterfront, all-suite resort on Rocky Point Island. Whether for business or a relaxing getaway, enjoy stunning bay views, tropical vibes, and home-like amenities—just minutes from Downtown Tampa, St. Petersburg, the Westshore District, and Tampa International Airport. Clearwater Beach is only 30 minutes away. This peaceful retreat offers easy access to it all while feeling blissfully away from the crowds.

Top guest favourite

Apartment in Tampa

4.95 out of 5 average rating, 312 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

Home in Tarpon Springs

4.94 out of 5 average rating, 231 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

Cottage in Tampa

4.97 out of 5 average rating, 211 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. Pet fee $50.

Guest favourite

Townhouse in Crystal Beach

4.94 out of 5 average rating, 163 reviews

Water view-Close to Trail & Gulf-Bikes, beach gear

* Walk/bike to St Joseph Sound (great for sunsets) * 10min to Honeymoon/Caladesi Islands * 1/2 block to bike/walk/run on Pinellas trail * 10min to downtown Dunedin & Tarpon Sponge docks * Screened patio w/fan * Fenced yard w/grill, a dock out to the pond, a fire pit * Beach chairs, towels and beach toys provided- even some fishing poles for the dock or pier! * 2 adult bikes provided * Fully stocked kitchen w/all amenities * WiFi/TV/streaming apps

Top guest favourite

Home in Oldsmar

5 out of 5 average rating, 143 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

Tiny home in Dade City

4.98 out of 5 average rating, 144 reviews

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, delight in the opportunity to interact with our friendly farm animals, adding a touch of rural charm to your agritourism escape.