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

Lux Beach Condo Waterfront Pool and Balcony
We enjoyed our stay the location, the views are spectacular. So homey and comfortable. A great place for a quite getaway but also plenty to do if you wanted to grab something to eat or sight seeing. Definitely recommend and hope to stay again son.

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

Sunshine getaway #2-Walk to Beach-King bed-Docks
The location was perfect for being able to go eat, shop and go to the beach. We didn’t rent a car and other than getting there and back we never had to uber anywhere. There’s so much available practically right next door. Would definitely recommend to anyone looking to be close to all the action at Johns pass.

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!

Seaside Chic #3 Waterfront Clearwater Beach
We had a truly peaceful and refreshing stay at this lovely home. The space was beautifully maintained, and perfectly situated for a relaxing getaway. Each morning, we were treated to the incredible sight of dolphins and manatees right from the property—a magical experience! And just a short 5-minute walk brought us to the Gulf, where we enjoyed breathtaking sunsets every evening. We also had the pleasure of meeting Lina and her husband, who were both kind and welcoming. It’s clear they take great pride in creating a space where guests can feel at home. I would absolutely recommend this home to anyone looking for a peaceful, nature-filled escape. We hope to return!

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
Perfection! Scott was such a responsive and accommodating host. Scott knew we had an early flight, and he let us check in as soon as their place was ready. Scott even made sure there was a pack n play for our little one, which exceeded our expectations. The location directly on the beach made sunsets after a busy day so relaxing. We got to see a lot of seabirds and dolphins right from the balcony. Everything we needed was there. The place was very clean throughout with a fully functioning kitchen and all necessary beach supplies. We made unforgettable memories for our first Florida family vacation, and we could not have asked for a better location with the best host. Thank you so much!

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

Ocean Sunsets & Downtown Biking Trails
We booked last minute as it was a last minute family trip and I have to say we all are glad we chose Denay’s place. The space was perfect for our family. The backyard was safe for the kids to play in. Since we rented the entire place (both units) we didn’t have to worry about bothering anyone when the kids were outside. It’s right next to Pinellas Trail so it was nice to be able to walk to the restaurants and have the kids used their scooters on the way there and back. Would definitely recommend!

Lake Oasis—Private Suite, Ducks Visit Daily!
What a great place. The ducks are very entertaining!

Tarpon Lake Escape LLC
I wish I could give 10 stars. We were so spoiled with all of the extra touches. I will let you be surprised. I cannot rave enough about how comfortable and welcome Julie has made it. Now, we want to come back in cooler weather and fish in the canal. The young man across the canal was fishing every morning early and he caught quite a few “eating size” Bass. Some of best restaurants are not far. Our favorites are Molly Goodheads, Ozona Blue Grilling, Rusty Bellies and Frenchy’s Outpost. Plus, there is a Trader Joe’s close by. Book it! You will be so happy!

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!

Lake Tarpon Waterfront-Private
It was a comfortable spacious home. Ideal for gathering with multiple people. Many amenities included. You could also separate into the warmth of different types of rooms. Laura allowed the family to bring their dogs which made everyone happy. It was close to main road and you could easily get to restaurants, stores or beaches.

Waterfront Pool Home with dock
We had a great time and the home was just a described. The kids are already read to return.

Apollo Beach Waterfront Amazing Pool Oasis
House was exactly as advertised, pool and atmosphere was extremely relaxing!

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 condo 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.

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.

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.

Sea La Vie- Studio by the bay!
I escaped MN to find this hidden gem! It was everything I could have asked for and more! I enjoyed the pool throughout my stay and catched a glimpse of a few dolphins. The bed was extremely comfortable and the unit was quiet. There was SPF and aloe in the bathroom cabinet which was perfect because I needed both! Walmart is a short uber away for all of your grocery needs. Doc’s next door was great to walk to for a quick dinner and drinks. The only hiccup I experienced was that pest control needed to enter the unit to spray and didn’t give Alison much notice so she could ensure I was out of the unit. I can’t wait to come back to this gem next year!

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.

Ocean Front Beach Condo Gap Day Special 6/12-6/20!
We had a lovely stay at 42 Gulf Blvd IRB! The house is comfortable, the beach area is peaceful and beautiful, and the location is perfect for a relaxing getaway. While we did experience a couple of issues during our stay, we truly appreciate how responsive and caring the management team was. They took our concerns seriously and handled the situation with professionalism and kindness. Their communication made all the difference. We would absolutely stay here again and highly recommend it to others looking for a laid-back and enjoyable beach experience!

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
G$6,276 GYD 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