
Waterfront holiday 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!

Waterfront studio w/Hot Tub and Putting Green
Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

A little piece of Heaven
2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

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.

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.

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

NEW Heated Salt Pool & Spa on Waterfront Canal
🏠 Welcome to this incredible, stunning & fully updated heated pool & spa home located on a serene waterfront canal of Tampa Bay! Enjoy the dock for fishing & relaxing. Fast WIFI, Samsung Smart TVs, a game room with an air hockey table, ping pong & pool table, and even a Pac-Man machine will make your stay memorable & fun! Most importantly, dive into this amazing heated pool & spa right in front of the canal!
Popular amenities for waterfront rentals in Oldsmar
Waterfront apartment rentals

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

Complete Renovation-everything new! Amazing views

Seaside Chic #3 Waterfront Clearwater Beach

Beach Front Condo!

Seminole Heights River Retreat - Central Tampa

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

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

Barefoot Beach Resort Indian Shores
Waterfront house rentals

Tampa Getaway Pool Home

Beachy Home On Water With Pool!

Relaxing Lake House

Piece of paradise in Indian Rocks Beach.

The Shore House

Stunning views! Spot dolphins from the pool!

Waterfront Gem Near Clearwater • Swim Spa + Nature

Preservation-Jacuzzi-Golf- Kayaks-Fishing-Pool !
Waterfront apartment rentals

Lovely Waterview Condo/ heated pool

Captain's Cove Waterside Condo 103 We are open!

2 Blocks To Beach: Walk to Restaurants & Bars-2BR

Tampa Bay Waterfront Views Rocky Point

Beach Front Madeira Beach

Amazing views on beachfront

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Modern Waterfront Condo - Captivating Sunset Views
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 £37 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oldsmar holiday 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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