
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.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65ā 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 Peteās, 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!

Beautiful Waterfront Home on the Alafia River.
Beautiful Waterfront Single Family home on the Alafia River leading to Tampa Bay and the Gulf of Mexico. Bring your boats, jetskis, Kayaks, water toys, fishing rods, etc. Riverview Civic Center and Boat Ramp is literally a couple of blocks away from the property and trailer parking is available at the property. If itās your lucky day, you will see manatees, dolphins, snook, redfish and stingrays right from the dock. Excellent fishing, restaurants and nightlife all on the river or by vehicle.

Bay Lake Cottage
Youāll 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 TVās, 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

Tampa Getaway Pool Home
Escape to paradise in this stunning and spacious 4 bedroom home with a private pool. Inside, you'll find endless entertainment options with smart TVs, a pool table, foosball table, indoor basketball arcade, and dart game. Centrally located, this home is just a short drive to some of Florida's top attractions including golf courses, the airport, Raymond James Stadium, Busch Gardens, the aquarium, downtown, the convention center, and popular beaches.

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 kitchenetteāproviding 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

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
Waterfront apartment rentals

Waterfront studio w/Hot Tub and Putting Green

Kayaks & Firepit Mins to Dwntwn!

Beach Front Condo!

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

Anchors UP #4, WALK to Beach; WATER VIEW; Sleeps 8

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

Waterfront studio! Heated pool and hottub

NEW! Amazing Beach & Sunset Views! Fully Renovated
Waterfront house rentals

Ocean Sunsets & Downtown Biking Trails

Waterfront Gulf Intercoastal Dockside Dream

Waterfront Resort with HEATED POOL!

*NEW* Riverside Retreat w/Pool

Luxury Waterfront w/ Private Heated Pool

Lakeview Chic 3BD House for golf/beach lovers

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

Lakeview Retreat with Private Pool Perfect Getaway
Waterfront condo rentals

Relax in a Newly Renovated Beach Front Paradise

Lovely Waterview Condo/ heated pool

Tiki Themed Waterfront Condo on Tampa Bay

Beach Front at āThe Shoreā

Spectacular beach to bay views from this resort.

Amazing views on beachfront

Indian Shores Gulf Front Rental

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $259 CAD | $311 CAD | $312 CAD | $229 CAD | $234 CAD | $216 CAD | $209 CAD | $230 CAD | $230 CAD | $223 CAD | $241 CAD | $230 CAD |
| 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 vacation rentals
Explore 20 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at $70Ā 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 guestsāaveraging 4.9 out of 5!
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- Rentals with a firepitĀ Oldsmar
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- Family-friendly rentalsĀ Oldsmar
- Rentals with a washer and dryerĀ Oldsmar
- Rentals with a hot tubĀ Oldsmar
- Rentals with a fireplaceĀ Oldsmar
- Hotel roomsĀ Oldsmar
- House rentalsĀ Oldsmar
- Rentals with outdoor seatingĀ Oldsmar
- Rentals with poolsĀ Oldsmar
- Pet-friendly rentalsĀ Oldsmar
- Rentals with beach accessĀ Oldsmar
- Waterfront rentalsĀ Pinellas County
- Waterfront rentalsĀ Florida
- Waterfront rentalsĀ United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
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- Weeki Wachee Springs
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- Coquina Beach
- Amalie Arena
- Vinoy Park
- Tampa Convention Center
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- Cortez Beach
- Hard Rock Casino
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- River Strand Golf and Country Club
- University of South Florida
- Busch Gardens
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