
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

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.

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.

Modern Waterfront Condo - Captivating Sunset Views
This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

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

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.

Breathtaking Waterview & Pool View Condo
Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

Lake Oasis—Private Suite, Ducks Visit Daily!
Charming private studio on the water with stunning lake views! Located in the heart of Tampa, this half-duplex is on a peaceful street, just 10 minutes from the airport, Bucs Stadium, and Busch Gardens, and 15 minutes from the local beach. Enjoy the wildlife right in the backyard with private water access—ducks, birds, turtles, and even iguanas visit daily!

Relaxing Lake House In Tampa
Welcome to Forest Hills Lakehouse, a peaceful and beautifully maintained lakefront home just minutes from Downtown Tampa and local favorites like Busch Gardens and Armature Works. This charming getaway combines serene outdoor living with easy access to the city’s best attractions — perfect for families, friends, or anyone seeking a rejuvenating stay.

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 accommodation

Beach-steps away! Waterfront Pool View!5

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

Waterfront Courtyard Condo 2 Blocks to Beach

Ocean Front Condo!

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

#1 -Sea Turtle Bungalows @John's Pass 1B/1B

Popular Beachside Studio w Relaxing Patio & Palms!

Waterfront Modern Chic #1 Clearwater Beach
Waterfront house rentals

River Home with Pool, Sunset, Dolphin & Fishing

Clearwater Lake House

Ocean Dreaming: Waterfront Home with Heated Pool,

Lake Tarpon Waterfront-Private

Lakeview Retreat with Private Pool Perfect Getaway

Luxurious "Riverfront Oasis" - Waterfront w/pool

Stunning views! Spot dolphins from the pool!

NEW Heated Salt Pool & Spa on Waterfront Canal
Waterfront condo accommodation

Waterfront Condo | Steps to Clearwater Beach 2King

Condo On The Beach - Heated Pool - Self Check-in

Beach Front Gulf View at John’s Pass Medeira Beach

Rocky Point paradise

Panoramic Summer Sunsets I Beachfront Condo + Pool

Updated Condo-Heated Pool-Private Balcony

Waterfront Condo With Pool and Multiple Views!

Waterfront • 2 King Suites • Walk to Beach • Pool
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 $43 AUD per night before taxes and fees

Verified guest reviews
Over 1,110 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Rentals with outdoor seating Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with pools Oldsmar
- House rentals Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with a patio Oldsmar
- Family-friendly rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with a fireplace Oldsmar
- Waterfront rentals Pinellas County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Tampa Convention Center
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- Lakewood National Golf Club
- The Don CeSar




