
Vacation rentals in Oldsmar
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Oldsmar
Guests agree: these stays are highly rated for location, cleanliness, and more.

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”
Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

Monterey Suite at Citrus Park
You will enjoy a sparkly clean Studio Suite with a private patio area and a peaceful lake view, comfortable adjustable queen bed, full bathroom, cute kitchen and computer station with high speed internet. Conveniently located ,14 minutes to airport/toll , walking distance to Super Walmart. Minutes to Citrus Park Mall , AMC Theaters , Publix, Costco, Sprouts, Airport, Busch Gardens, Raymond James Stadium, NY Yankees Training Camp, Upper Tampa Bay Trail were you can rent bikes and many more.

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

Guest House in prime location!
This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

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, WiFi, 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. Dogs okay, sorry no cats, pet fee $50.

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’

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

Tropical Oasis Retreat w/ Heated Pool
Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

Tiny House Oasis | Best Location | Outdoor Shower
Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor literally around the corner from Main Street. This light, private and 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.

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.

BeachBunkies Cottage 1. Four miles to the beach!
Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.

Grove Keepers Cottage
This private vacation unit is an upstairs unit with a private entrance, 1 bedroom with a king bed, 2 guest, balcony off the master suite. Spacious living area ,designated work space, kitchenette , balcony off of bedroom. All our units are non-smoking and vaping.
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar

The Enchanted Lodge

Sunny Oasis: Villa Retreat

Casa Del Sole

Entire Guest House near Tampa airport

"Sweet Harbor Cottage" Walk to Downtown

Cozy Private 2BR FL condo

Modern2-Story Home -Perfect for Family & Business!

Modern Private Estate | Central to Tampa & Beaches
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ632 | ﺩ.ﺇ687 | ﺩ.ﺇ683 | ﺩ.ﺇ602 | ﺩ.ﺇ588 | ﺩ.ﺇ569 | ﺩ.ﺇ569 | ﺩ.ﺇ606 | ﺩ.ﺇ544 | ﺩ.ﺇ577 | ﺩ.ﺇ606 | ﺩ.ﺇ613 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Frequently Asked Questions
Where should I stay in Oldsmar?
Make yourself at home in Oldsmar by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in East Lake Woodlands, over 580 vacation rentals in The Grove Of Laforest, and over 580 vacation rentals in Oldsmar.
Are there pet-friendly vacation rentals in Oldsmar?
Four-legged friends are welcome in Oldsmar. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oldsmar?
Yes! Work meets play with ease at over 80 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Oldsmar vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oldsmar have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oldsmar have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Oldsmar have wifi?
Absolutely! We offer over 20 hotel rentals with wifi in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Oldsmar have a gym?
Absolutely! We offer over 20 hotel rentals with a gym in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Oldsmar?
Experience the best of Oldsmar with our hotel rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly hotel rentals in Oldsmar?
Oldsmar has more than 10 family-friendly hotel rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Oldsmar

Total vacation rentals
Explore 150 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 3,920 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
140 of Oldsmar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Waterfront rentals Oldsmar
- Rentals with pools Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a fire pit Oldsmar
- House rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with a washer and dryer Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Pet-friendly rentals Oldsmar
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
- Busch Gardens
- Gulfport Beach Recreation Area
- The Don CeSar
- Lakewood National Golf Club




