Vacation rentals in Oldsmar

4.97 out of 5 average rating, 259 reviews

An electric coffee maker is positioned on a marble countertop, beside a light-colored ceramic mug. The coffee maker features a sleek black design with a prominent power button and is plugged into an electrical outlet on the wall.

Guesthouse in Tampa

Cozy-Private apartment, private entrance & parking

A cozy place to have your vacation in Tampa, private entrance and parking. Cozy and romantic to enjoy as a couple to your liking. Located in a central area of Tampa, close to Bush Garden, Adventure Island, Raymond James Stadium, Tampa International Airport, Ybor City, Downtown Tampa, Amalie Arena, River Walk, Internacional Mall, Citrus Park Town Center,Aquarium,Lowry Park Zoo, Clearwater Beach and more! Peaceful and centrally-located place with very good restaurants and a wide variety of shops.

Guesthouse in Palm Harbor

A screened-in patio surrounds a rectangular swimming pool, which is bordered by paver stones. Lounge chairs are positioned under large umbrellas, providing shaded seating. A decorative rooster figure stands beside the pool, contributing to the outdoor ambiance.

4.97 out of 5 average rating, 309 reviews

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

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Guesthouse in Palm Harbor

The bathroom features a walk-in shower enclosed by a black-framed glass door, complemented by modern tiled walls. A circular mirror is mounted above the vanity, which offers essential bathroom accessories. A wooden shelf displays neatly rolled towels, adding a touch of organization.

4.9 out of 5 average rating, 141 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

4.98 out of 5 average rating, 112 reviews

Bungalow in Oldsmar

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

4.78 out of 5 average rating, 262 reviews

Home in Tampa

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

4.96 out of 5 average rating, 219 reviews

A modern kitchenette features white cabinetry and a grey tile backsplash. Stainless steel appliances, including a microwave and fridge, are included. A dining setup with two bar stools is positioned at a quartz countertop, complemented by black dinnerware, enhancing the functionality of the space.

Apartment in Tampa

Soothing Breeze

This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Nearby Places: TPA Airport 12 miles, 15 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

The grotto pool features natural rock formations, surrounded by tropical foliage and palm trees. Two lounge chairs are positioned near the water's edge, and the pool area is framed by a white railing that complements the inviting landscape.

5 out of 5 average rating, 141 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

4.99 out of 5 average rating, 178 reviews

A spacious living area is illuminated by recessed lighting, featuring a sleek black sofa and a mounted television. A wood countertop is complemented by a black chair in the kitchenette. The neutral walls and large window provide a bright, inviting atmosphere.

Apartment in Clearwater

Welcome to your cozy studio!

This charming furnished studio apartment is the perfect blend of comfort and convenience, offering everything you need for a delightful living experience: *Fully Furnished *Comfortable Sleeping Area *Equipped Kitchenette *On-Site Laundry Room *Private Parking Space *Private Patio Prime Location: Conveniently located close to shops, restaurants, parks and just 10 minutes away from the breathtaking Clearwater Beach

4.84 out of 5 average rating, 177 reviews

Apartment in Tampa

Hotel "Amanecer" a paradise where you will find peace.

Cozy apartment in the sunshine state! This fantastic, recently renovated piece of heaven has all the benefits of a private suite at a single room rate. Centrally located in the heart of Tampa Bay, you'll be minutes away from enjoying all of Tampa's top attractions (Tampa International Airport, Clearwater Beaches, Bush Gardens, Adventure Island, and more) and will absolutely enjoy your stay.

An open layout is presented, connecting a bright dining area with a modern table and white chairs to a sunlit living space. French doors frame a view of a private sunroom adorned with tropical plants, enhancing the sense of spaciousness and tranquility.

4.86 out of 5 average rating, 100 reviews

Private In-Law Suite with Beautiful Bay View

This is not just a room. It is a beautiful and generous suite with your private living room over looking the old Tampa Bay. In the morning, you can enjoy your coffee while listening to birds singing; in the evening, you can enjoy the sunset on your dinner table. It is minutes from parks, from shopping centers, 15 minutes from beach, and 25 minutes from the airport.

Guesthouse in Safety Harbor

A charming gazebo features an intricate design with a green roof, surrounded by well-maintained grass and trees. A paved walkway leads to the structure, and nearby benches provide places to sit and enjoy the outdoor scenery. Lush landscaping enhances the peaceful setting.

4.93 out of 5 average rating, 272 reviews

Tiny House Downtown, Superb Location

Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor around the corner from Main Street. This light, airy gem comes completely equipped to hang out for a while. See what all the tiny home excitement is about! Now with new AC mini split for quieter and more comfortable air.

4.96 out of 5 average rating, 297 reviews

The charming exterior of the cottage features a bright yellow door framed by flowering window boxes. A spacious front porch with screening provides a welcoming entryway, while a pathway leads to a well-maintained lawn bordered by a white picket fence.

Cottage in Oldsmar

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Oldsmar vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Oldsmar

4.69 out of 5 average rating, 231 reviews

Home in Tampa

Tampa Bay Cozy apartment

ManuelRating, 5 stars1 week ago

Place was just like the pictures and descriptions definitely I will be back soon

A sitting area is featured in the lanai, surrounded by large glass panels. A woven chair offers a cozy seating option alongside a low wooden table. A green wall adorned with the word 'Chill' adds a touch of relaxation, complemented by a circular black rug on the tile floor.

4.93 out of 5 average rating, 58 reviews

Sunny Oasis: Villa Retreat

GemmaRating, 5 starstoday

This air bnb was really great. Kyle was really helpful and went out of his way to make sure we had everything we needed. The house had all things needed for a very comfortable stay and was in a great neighbourhood. Would definitely stay again if we come back to Florida!

4.83 out of 5 average rating, 23 reviews

Sunny's Retreat

VanessaRating, 5 stars2 weeks ago

Great place to stay on a family vacation. Lots of restaurants in the surrounding areas. Home was very welcoming and the owners were very nice and responsive to any and all questions we had. Patio area was very nice and accommodating. Host was very nice and stayed in contact with me the entire trip. They were also willing to take care of a small issue with no hesitation and that speaks volumes to their willingness to help make sure their guests have an amazing experience. We look forward to our next trip! Thank you.

4.96 out of 5 average rating, 103 reviews

A bright studio features a spacious bed with navy bedding and a light-colored headboard. A kitchenette is visible in the corner, equipped with a refrigerator and microwave. A small desk and chair are positioned nearby. A ceiling fan provides additional comfort.

Guest suite in Tampa

Studio with private entrance and bathroom

SatoshiRating, 5 stars5 days ago

Great place. Clean and comfortable.

4.93 out of 5 average rating, 27 reviews

A large swimming pool is surrounded by well-maintained landscaping and a variety of poolside loungers. Tall palm trees and green shrubs add to the serene setting, while shaded umbrellas provide comfort for relaxation. The area is quiet and inviting, enhancing the outdoor experience.

Condo in Oldsmar

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

LouiseRating, 5 stars6 months ago

Sylvia was a great host and very responsive. The location was great and close to family. The view from the condo was spectacular with beautiful sunsets. Great for bird watching. Nice quiet area. Would recommend to family and friends.

An outdoor stage is set for a performance, featuring a band illuminated by colorful lights. A crowd enjoys the show, seated on chairs and blankets. Tents are visible nearby, with trees surrounding the area, indicating a lively community event at night.

4.86 out of 5 average rating, 22 reviews

Walk to the water from this pet friendly home!

DavidRating, 5 stars1 week ago

beautiful space. surrounded by beautiful nature. quiet. lots of light with the skylights. gorgeous remodeled bathroom. if you need a quiet respite for your trip, this is the spot. thank you!

4.97 out of 5 average rating, 86 reviews

A modern kitchen corner features a sleek induction cooktop alongside a stainless steel toaster and a single-serve coffee machine. The countertop displays a light color which contrasts with the dark wood cabinetry. Geometric backsplash tiles add texture to the cooking area.

Guest suite in Tampa

Cozy guest suite.

MatthewRating, 5 stars1 week ago

We really enjoyed our stay at this Air BnB! We have been hosts ourselves and loved everything about our stay at Yusleidys’s private suite; from the cleanliness, decor and adorable private outdoor area to the friendliness and courtesy of our hosts. The amenities were also exceptionally thoughtful. What a great value for the price! We definitely recommend this booking!

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.