
Waterfront holiday rentals in Oldsmar
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Oldsmar
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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

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 the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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

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.

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!

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.

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.

Cabin 1 - Marigold Moments
Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay.

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

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

Lakeview Retreat with Private Pool Perfect Getaway
Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

Palm Hideaway on the Cotee River
Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy the fire pit or paddle the kayaks.
Popular amenities for Oldsmar waterfront rentals
Waterfront apartment accommodation

Anchors UP #2, WALK to Beach, 1 bed/1 bath apt.

Waterfront studio great for Pasco scallop season!

Kayaks & Firepit Mins to Dwntwn!

15 Steps to the Beach! 2 Bedroom Beach Paradise!

Beachy Bayfront Condo Walk to Beach

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

Forever Sunshine - Fully Renovated

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6
Waterfront house rentals

River Front Heated Pool Estate-Busch Garden/USF

Ocean Sunsets & Downtown Biking Trails

Sunny's Retreat

Canal-front Sanctuary | Manatees, Pool, Hot Tub

Oceanfront Escape | Private Beach | Cozy & Quiet

Waterfront home w/dock-Kayaks & Jon Boat included!

NEW Heated Salt Pool & Spa on Waterfront Canal

Waterfront Gem Near Clearwater • Swim Spa + Nature
Waterfront condo accommodation

Sage & Sea Retreat | Bay View - Heated Pool

Tiki Themed Waterfront Condo on Tampa Bay

Tampa Bay Waterfront Views Rocky Point

Spectacular beach to bay views from this resort.

Amazing views on beachfront

Walk to Beach, Bars, and Restaurants Nearby

Modern Waterfront Condo - Captivating Sunset Views

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $266 AUD | $319 AUD | $320 AUD | $234 AUD | $240 AUD | $222 AUD | $214 AUD | $236 AUD | $236 AUD | $229 AUD | $247 AUD | $236 AUD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about waterfront rentals in Oldsmar

Total holiday rentals
Explore 20 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $71 AUD per night before taxes and fees

Verified guest reviews
Over 1,120 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Oldsmar holiday rentals include Wi-Fi 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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- Fitness-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
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- Family-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a patio Oldsmar
- Hotel rooms Oldsmar
- House rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with outdoor seating Oldsmar
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