Waterfront vacation rentals in Oldsmar

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Oldsmar

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Tampa

4.99 out of 5 average rating, 139 reviews

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, 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. Pet fee $50. Elope/Proposal packages IG lakepossibility

Aug 21 – 28

G$37,202 GYD per night

Guest favorite

Home in Palm Harbor

4.94 out of 5 average rating, 183 reviews

Private Entrance/Well Appointed Suite/ Lake View

Private entrance/ Private suite/bath w/ walk in closet. Microwave/fridge. Convenient parking. Beautiful view of the lake and all its wildlife. Everything you need to go to the beach is in the room, beach towels, umbrellas, beach mat. Due to host allergies, NO pets/animals/service animals. No smoking/vaping/drinking/drunkenness. Sensitivities? I do not use plug-ins, scented sprays, scented detergents/dryer sheets. If traveling w/ a service animal, kindly, please choose another Airbnb property.

Aug 3 – 10

G$16,966 GYD 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.

Feb 22 – Mar 1

G$35,667 GYD per night

Guest favorite

Home in Largo

4.96 out of 5 average rating, 100 reviews

Stars by the Sea - Cozy home close to beaches

Our home has been beautifully updated, fully furnished and decorated in a beach theme. The master bedroom has a comfortable king size bed and the second bedroom has a queen. We have a beautiful pond in the back. Perfect for you to relax and BBQ while enjoying our wonderful Florida weather. The house has a Smart TV, Cable, Internet w/WiFi, dishwasher, washer, dryer, etc. Everything you need to make your stay perfect. We are close to great shopping, dining and to some of Florida's best beaches.

Jul 23 – 30

G$27,188 GYD per night

Guest favorite

Condo in Palm Harbor

4.8 out of 5 average rating, 155 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

G$19,082 GYD per night

Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 225 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

This cozy one bedroom, one bath condo is only 2 blocks from the beach with family-friendly activities, nightlife, and public transportation nearby. The place is perfect for solo travelers, couples, & even small families who looking to have a relaxing time. Located right on the intercostal waterway. You can enjoy your coffee on the dock while watching the sunrise. Also, a great spot for seeing dolphins. Shops, food , and entertainment are all located within walking distance. BTR #266

Sep 12 – 19

G$24,906 GYD per night

Guest favorite

Condo in Tampa

4.95 out of 5 average rating, 131 reviews

Waterfront condo with sunset views of Tampa Bay.

This newly furnished condo features a balcony with waterfront views of Tampa Bay and amazing sunsets. Includes a heated pool, volleyball court, BBQ and fire pit as well as on-site laundry. Just minutes from Tampa International Airport. Near Clearwater and other desirable beaches. Nearby attractions include Busch Gardens, Adventure Island, the Port of Tampa, Historic Ybor City, Tampa Bay Performing Arts Center, Tropicana Field, Amalie Arena and Raymond James Stadium.

Oct 1 – 8

G$31,319 GYD per night

Guest favorite

Condo in Tampa

4.94 out of 5 average rating, 215 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.

Jun 10 – 17

G$31,164 GYD per night

Guest favorite

Home in Tampa

4.83 out of 5 average rating, 120 reviews

Beautiful two bedroom w/ pool table & free parking

Lovely and safe neighborhood. Pool table, grill , hammock, fire place, free parking, bar for drinks. Kitchen fully equipped. Big backyard, children and pets friendly. 4 TV’s in the house, one queen bed and one full bed. Enough space to fit more people. Extra sheets and pillows. Everything is new and clean. Enjoy the close amenities. Ven T Davis Beach 24 min away, Bush Gardens 15 min away, Ybor City 20 min away. Raymond James Stadium 17 min away.

Feb 15 – 22

G$27,052 GYD per night

Guest favorite

Guest suite in Oldsmar

5.0 out of 5 average rating, 116 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 26 – Dec 3

G$51,374 GYD per night

Guest favorite

Guesthouse in New Port Richey

5.0 out of 5 average rating, 103 reviews

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 was completely renovated in 2022 & 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 a fire in the fire pit or paddle the kayaks.

Nov 18 – 25

G$19,326 GYD per night

Guest favorite

Guest suite in Lutz

4.94 out of 5 average rating, 125 reviews

3 Room Suite Private Entry on Lakeside Homestead

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.

Jun 30 – Jul 7

G$21,343 GYD per night