
Waterfront holiday rentals in Oldsmar
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Top-rated waterfront rentals in Oldsmar
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Popular amenities for waterfront rentals in Oldsmar
Waterfront apartment rentals

Anchors UP #3, WALK to Beach, 1 bed/1 bath
Great location! Easy access for boating. Highly recommend staying there!

~ Luxurious Waterfront Hideaway ~ 11m to Downtown!
Had a wonderful 2 weeks here. Jessica was very helpful and obliging. Will definitely be coming back. Beds and pillows super comfortable. Everything was here that we needed.

Kayaks & Firepit Mins to Dwntwn!
The place was so cute and right in the middle of everything. If I ever find myself staying over in the Tampa area again, this will definitely be somewhere I come back to!

Beach Front Condo!
We enjoyed everything about the condo and the area! Was clean and directly looked over the ocean!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath
We absolutely loved our stay at Scott’s place. The condo was sparkling clean- I am extremely picky about cleanliness and was not disappointed. The kitchen was well equipped and we appreciated all of the beach gear Scott had available for use. We loved the location and the view from the balcony is unmatched. Scott was quick to respond with the minor issue we had at check in and quickly resolved the issue. We had the best time and will definitely be back!

2 PM check in-water view from Balcony-Pool
The condo was clean and location is convenient to the airport and other Tampa attractions.

Popular Beachside Studio w/ Shady Patio & Palms!
Had a great time staying here! We can for a long weekend and Lara was super helpful to accolade us for showing up early and wanting to get our beach vacation started! The until was so cute and perfect for 2 people. The beach is literally steps from your door. Made it easy to go back and forth if we forgot something inside or if we needed to take a couple trips to get all of our beach gear set up. There wasn’t a ton to do near on treasure island so we took a quick 20 minute uber into St. Pete’s which has so much to do, great restaurants, and awesome night life!

The Oasis
Russell’s place was just as described. The bay of the bay was beautiful! This condo was within short driving distances of many great local beaches and restaurants. It had all the amenities, linens, and other items needed to make our stay perfect. Russell checked in with us prior to our stay, during and after.
Waterfront house rentals

Quiet Oceanside Getaway - PALM HARBOR, FL
The space and location were ideal for our needs. The house is very spacious and comfortable. The pool was great very convenient!

* House with Dock and Direct Access to the Gulf *
I felt this place was too good to be true … but having stayed 4 nights, I can positively say this place way exceeded our expectations!!! We’ve already talked to our family that we will be regulars when we come to Palm Harbor to visit. Thank you Ruth for sharing your amazing place (and boat and kayaks and paddle boards) with us!! We will definitely be back!!

Luxury Waterfront w/ Private Heated Pool
We absolutely LOVED this house and will probably make it an annual trip. The house is gorgeous and soooo well stocked! My whole family enjoyed the house and the games downstairs! The snacks and personalized note was such a thoughtful touch. What a fantastic spot! Chris was great too! 10/10 would recommend this listing!

Relaxing 3BR/2BA POOL Home w. Pond View & HOT TUB
Thank you for hosting us! The home is beautiful. Great neighborhood and loved all the extra touches. This was a home away from home. We were very comfortable, safe, and loved the pool! We hope to be back in the near future. Thank you!

Beautiful two bedroom w/ pool table & free parking
the house is really nice. we really enjoyed the screened porch and pool table even though it was unlevel and there was only one usable cue stick. it was kinda like a mix of putt putt and pool haha :) it was also nice that there were doggy doors.

4BR Heated Pool Relaxation Home | Airport | Beach
Excellent service, attention and good service

Guest studio on Bayshore in So. Tampa
Quiet and nice location - close enough to Raymond James Stadium for our Metallica show - (20-$25 Uber XL) 2 houses off the bay where there is a nice biking / walking sidewalk along the water. Great host, very quick to respond. Also there is Berns Steakhouse around the corner - booking in advance? Their reservations at Berns are 60 days out and a must eat - take the tour after dinner and enjoy the dessert rooms after that. Also Wrights Deli is the go to spot for lunch and worth the wait there.

Casa Sea Belkis/Beach/Mini Golf/BBQ/Games/Bikes
The house was clean and comfortable. The location was close to things we wanted to do so that was great. The neighborhood was quiet and peaceful. We communicated with our hosts using the app prior to our arrival but had no questions or problems after arrival so no need to communicate with them. We enjoyed our stay very much.
Waterfront apartment rentals

Tampa Events & Suite w/WtrFrt Bay & Sunset Views
Such an awesome place to stay with amazing views. Clean and had extra essentials which makes it nice. Loved the fan and TV above the bed and the large shower. I traveled alone and felt completely safe. I would definitely stay again.

Waterfront condo with sunset views of Tampa Bay.
We really enjoyed relaxing by the pool and having the Big Bamboo bar / restaurant on the premises made it so convenient. The bed was comfortable and shower pressure good. We also appreciated the coffee bar.

Heron's Hideaway- Studio by the bay!
What a treasure!! Though small, it completely met our needs. Was clean and homey. Ideal location between downtown Saint Pete and the beaches. Loved the view of the water from the balcony. Kids loved the pool.

Tampa Bay Near by Airport & Stadium
This place was perfect! We found that whatever we needed or forgot was provided in the condo. The beds were comfy, lots of pillows, and loved sitting with our coffees (lots of varieties) on the balcony. Definitely be returning.

Rocky Point paradise
It was a very clean place and a great location. We were there to attend an event at Raymond James which was only a short drive, and close enough to the beach to enjoy that as well. The balcony was nice and private. We loved being able to just sit and enjoy the peaceful water view!

Amazing views on beachfront
It was a great stay with plenty of space and easy access to the beach. Just what we anticipated.

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
Just like the photos! Beautiful and comfortable for our stay… Love the location, close to everywhere we wanted to go! Comfortable bed, the couch could use some updating. The pool is very warm, but a nice spot to hang out. Didn’t get to see any dolphins 😞 Overall, enjoyed our stay, will definitely be back!

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
Great area. Great view. Awesome pool/ bar area!
Quick stats about waterfront rentals in Oldsmar
Total rentals
20 properties
Nightly prices starting at
$38 SGD before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Ben T Davis Beach