
Waterfront holiday rentals in Oldsmar
Find and book unique waterfront rentals on Airbnb
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 £30 per night before taxes and fees

Verified guest reviews
Over 1,180 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!
Top-rated waterfront rentals in Oldsmar
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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!

Waterfront studio great for Pasco scallop season!
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.

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.

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

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.

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.

1928 Riverfront Bungalow with boat dock
Waterfront ranch Bungalow. Quaint with FP, orig refin hardwood floors, New kitchen with SS appliances, granite countertops, 2 master suites, one with river views. Screened in front porch, garage & floating dock. Washer & dryer. Completely furnished with antiques. Walking path along the river. Step back in time.
Popular amenities for waterfront rentals in Oldsmar
Waterfront apartment rentals

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

Coastal Waterfront Condo Steps to Beach

Kayaks & Firepit Mins to Dwntwn!

Direct Beachfront Condo, Ocean balcony view!

Seminole Heights River Retreat - Central Tampa

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

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

Tampa | Heated Pool • Waterfront • Pet Friendly

Oceanfront Escape | Private Beach | Cozy & Quiet

Luxurious "Riverfront Oasis" - Waterfront w/pool

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

NEW Heated Salt Pool & Spa on Waterfront Canal

Waterfront Gem Near Clearwater • Swim Spa + Nature

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Tree House Treasure
Waterfront apartment rentals

Tampa Bay Waterfront Views Rocky Point

Rocky Point paradise

Beachfront in exclusive resort

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Walk to Beach, Bars, and Restaurants Nearby

Modern Waterfront Condo - Captivating Sunset Views

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

*Shore Thing* Walk to Beach | Intercoastal Views
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £139 | £167 | £168 | £123 | £126 | £116 | £112 | £124 | £124 | £120 | £130 | £124 |
| 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 |
Destinations to explore
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- Rentals with a hot tub Oldsmar
- Rentals with outdoor seating Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with pools Oldsmar
- Family-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a firepit Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a patio Oldsmar
- Hotel rooms Oldsmar
- House rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Waterfront rentals Pinellas County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Bean Point Beach
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Vinoy Park
- Hard Rock Casino
- University of South Florida
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Epperson Lagoon
- Sand Key Beach
- Weeki Wachee Springs State Park
- Anna Maria Public Beach
- MidFlorida Credit Union Amphitheatre
- River Strand Golf and Country Club
- Cortez Beach
- Busch Gardens





