Vacation rentals with a pool in Oldsmar

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Top-rated rentals with a pool in Oldsmar

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Dunedin

4.93 out of 5 average rating, 119 reviews

Everything you'll need, plus! Park Model RV

A relaxing and open space great for beach lovers, cyclists, and people who love the outdoors. This cozy setting provides all the necessities for daily living, plus more to make for a great get away! Accommodates up to four. Within 2 miles of Honeymoon Island State Park and Caladesi Island. Easy drive to Clearwater Beach, St. Pete's Airport and surrounding areas. Short walks to town, bike trails and beautiful Gulf coast sunsets make this a perfect getaway or home base for exploring the area.

Aug 11 – 18

R1,897 ZAR per night

Guest favorite

Condo in Tampa

4.94 out of 5 average rating, 145 reviews

Lovely Waterview Condo/ heated pool

Entire suite waterfront condo. Quiet peaceful place with an amazing front waterview is very central to access the entire Tampa Bay area. Just 5 mins from Tampa International Airport10 mins to Raymond James stadium, 10 mins to International Mall , 15 mins to downtown Tampa , Ybor city and more, We are located in Tampa Bay in a condominium ( but we are not part of it) Private balcony, unit is equipped and accommodated with the essentials to provide you a great stay during visit in Tampa FL.

Jan 27 – Feb 3

R3,162 ZAR per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 202 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Dec 10 – 17

R2,217 ZAR per night

Guest favorite

Guest suite in Tarpon Springs

4.95 out of 5 average rating, 108 reviews

Private suite in heart of Tarpon Springs!

House centrally located in a safe, residential area. Enjoy a clean, cozy & comfortable private suite with private entrance! Next to Downtown Tarpon, Tarpon Springs Sponge Docks, Sunset Beach, Safety Harbor, and many other attractions. Less than 5 minutes from the beach! Enjoy fast wifi, cable, and a cozy queen bed! Full kitchen. During your stay you’ll have access to bicycles, plenty of beach towels, hats, beach toys. Beach chairs, chairs umbrellas, small cooler and a variety of sunscreens

Jul 10 – 17

R1,940 ZAR per night

Guest favorite

Home in Palm Harbor

4.99 out of 5 average rating, 101 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. We are pet friendly! When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round.

Jan 4 – 11

R5,334 ZAR per night

Guest favorite

Condo in Palm Harbor

4.8 out of 5 average rating, 156 reviews

Lakeside 2- Bed Apartment Near Clearwater Beaches

Ideally located on Florida's Gulf Coast minutes from many of America’s best beaches. The apartment is situated on the shores of beautiful Lake Tarpon, just north of Clearwater. The big exciting city of Tampa is just 30 mins away with the big theme parks in Orlando only 90 mins away. The pool & jacuzzi are also by the water & decking. Come stay, relax & recharge your batteries in a comfortable peaceful setting yet close by you have all the activities & amenities that you could ever wish for!

Aug 31 – Sep 7

R1,674 ZAR per night

Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 459 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

Nov 11 – 18

R2,036 ZAR per night

Guest favorite

Guest suite in Largo

4.95 out of 5 average rating, 234 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

Oct 8 – 15

R1,684 ZAR per night

Guest favorite

Apartment in Dunedin

4.95 out of 5 average rating, 168 reviews

Mermaid cottage

Watch this video first to experience the property https://vimeo.com/444390022 Cute little cottage poolside with a pond out front, great kitchen, plenty of space to kick back and relax, private front porch with a table and two chairs NOTE: If booking 28 days or more Please be advised this listing has a 45 DAY cancellation policy which is less strict than the airbnb cancellation policy that is listed , Airbnb will call and confirm that I honor this less punitive cancellation policy.

Dec 16 – 23

R3,237 ZAR per night

Guest favorite

Home in Palm Harbor

4.98 out of 5 average rating, 112 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our “sun-kissed” get-away in beautiful, conveniently located, Palm Harbor, FL. In less than 10 minutes you can find yourself sitting on the shore of one of our award-winning white sandy beaches or teeing off at a pristine golf course, and only 30 minutes from Tampa attractions. There is plenty of space to sleep 6 very comfortably, a beautiful bird caged pool and outdoor seating/lounging, BBQ grill, and fun for everyone. Come and enjoy...you just might not want to leave!

Aug 7 – 14

R5,335 ZAR per night

Guest favorite

Condo in Tampa

4.94 out of 5 average rating, 216 reviews

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. Guests will have full access to the resort where they can enjoy the side pool bar, heated pool, fire pit, coin operated laundry and dryers. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

Jul 6 – 13

R3,130 ZAR per night

Guest favorite

Guest suite in Oldsmar

5.0 out of 5 average rating, 118 reviews

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

Nov 6 – 13

R4,649 ZAR per night