
Waterfront vacation rentals in Oldsmar
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Top-rated waterfront rentals in Oldsmar
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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!

Cabin 3 - Nasturtium Nest
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. We look forward to seeing you on the Farm!

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.

The Hawk's Nest at Alligator Creek
Nestled in the heart of Clearwater, Hawk’s Nest is a peaceful, private artist's retreat reminiscent of Tennessee or North Carolina. Surrounded by nature, it feels like living in a treehouse! Sports fans will love being near two Spring Training stadiums and just 25 minutes from Raymond James. Only 20 minutes to the beach, and centrally located for shopping and activities. A safe, gated property offering peace and convenience. Unforgettable! Also available for longer stays.

The Guest House at Riverbend Retreat Fla.
True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

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

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

Spacious Lakehouse Suite - Nature Lover's Paradise
Bright, clean & well appointed Private patio entrance Includes bedroom, private bathroom & sitting room with TV, microwave, etc. PLEASE TAKE NOTE: the suite shares walls & closed/locked doors with host's home. Spacious lakeside deck & canoe FOR A PRIVATE/ROMANTIC GETAWAY consider our other listing on the property - Miss Ruby, our fully renovated vintage camper with open-air shower and bath-house.

The perfect lake house getaway near the airport.
Relax with the whole family in this cozy residence in the Tampa Bay area. Enjoy the spacious backyard and unwind in the hot tub with peaceful views of the lake. Set in a centric location near the International Airport, Raymond James Stadium, Busch Gardens, Adventure Island, Citrus Park mall and Florida's best-rated beaches.
Popular amenities for Oldsmar waterfront rentals
Waterfront apartment rentals

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

Bright Waterfront Apt | Minutes to Tampa Airport

We cross 102

Kayaks & Firepit Mins to Dwntwn!

Relaxing waterfront retreat

Ocean Front Condo!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Waterfront Modern Chic #1 Clearwater Beach
Waterfront house rentals

Lake it easy

Ocean Sunsets & Downtown Biking Trails

Tampa Getaway Pool Home

Kayak and Fishing Waterside Retreat

Lakeview Retreat with Private Pool Perfect Getaway

Preservation-Jacuzzi-Golf- Kayaks-Fishing-Pool !

Chic|Pool|PuttingGreen|Beaches

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes
Waterfront condo rentals

Relax in a Newly Renovated Beach Front Paradise

Waterfront Condo | Steps to Clearwater Beach 2King

Beachfront Condo with Centerline Sunsets

Spectacular beach to bay views from this resort.

Amazing views on beachfront

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Modern Waterfront Condo - Captivating Sunset Views

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
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 ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,110 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Oldsmar vacation 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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- Rentals with a washer and dryer Oldsmar
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- Family-friendly rentals Oldsmar
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