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

Entire Guesthouse - Tampa
Looking for a great stay in Tampa? This is the perfect place! One bed bedroom and one bath upstairs guest house that is detached from the main house. Located in a family-friendly neighborhood, this gem is centrally located to everything Tampa has to offer. Pool is not part of listing. Parking is in the street in front of house. No more than 1 vehicle per renter. Perfect for short term stay! Close to: TPA - 12 min Downtown Tampa - 8 min Raymond James Stadium - 10 min Amelie Arena - 9 min

The Fremont, Villa 3. Walk to Hyde Park!
Stunning design and exceptional location just steps from Hyde Park Village and Soho make this the perfect fit for your next stay in Tampa. This one bedroom luxury private villa was built specifically for Airbnb and just completed in March of 2024! The 14 foot vaulted ceilings and white oak cabinetry make this unit feel like a luxury hotel! Traveling for a few nights or a few months, this unit has it all. Extremely spacious and beaming with natural light this unit will not disappoint!

Private Pool Home Near Clearwater & Tampa
Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

Boho Oasis • Pool •Fire Pit • Near Beach & Airport
Welcome to my 3-bedroom, 2-bath Airbnb home in vibrant Tampa, Florida. BoHo Zen-style oasis, complete with a pool, BBQ area, and ping pong table, provides the perfect backdrop for your getaway. Just 15 minutes from the airport and the Bay Area. centrally located near major stores, convenience is at your doorstep.. Fully equipped kitchen and bedrooms are beautifully decorated, offering comfort and restful nights can't wait to host you and share this peaceful haven with you…😌

Cozy Retreat! Walk to Crystal Beach/Park
Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

Peaceful Pet friendly 2 BR cottage with hot tub.
Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today and experience the tranquility of country living!

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

The perfect lake house getaway near the airport.
Relax with the whole family in this cozy residence in the Tampa Bay area. Enjoy the spacious backyard and unwind in the hot tub with peaceful views of the lake. Set in a centric location near the International Airport, Raymond James Stadium, Busch Gardens, Adventure Island, Citrus Park mall and Florida's best-rated beaches.

MODERN/Mins to Beach/walk to dwtn/Free parking
🌴 Escape to Tarpon Springs! This newly renovated 1B/1B private home is perfectly located—just 5 minutes to the beach and the famous Sponge Docks, and a short stroll to charming downtown. Whether you’re here to relax, explore, or soak in the local culture, this getaway puts you right in the heart of it all.

Modern 3 Bedroom 2 Bathroom House
Experience the charm of Tarpon Springs from our newly renovated 3-bedroom, 2-bathroom family retreat. Just minutes from Lake Tarpon and a short drive to the iconic Sponge Docks, authentic Greek eateries, Fred Howard Beach, the Pinellas Bike Trail, and countless other local gems.

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.
Popular amenities for Oldsmar house rentals
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Zen Holistic Retreat by Carrollwood/Westchase

Tropical Getaway w/Heated Pool & King Beds

Rooms with a Pool

NEW Heated Salt Pool & Spa on Waterfront Canal

Coastal Escape: heated saltwater pool & playground

FREE Heated Pool & Spa l Book your Winter Vacation

The T and C Club
Weekly house rentals

Casual, relaxing 2/2 SFH remodeled, in Dunedin.

Central Clearwater | 3BR Modern Retreat

Casa Del Sole

Palm Harbor Retreat | 2BR/2BA Near Gulf Coast Fun

Downtown | Pure Comfort | Dogs Welcome

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Traditional Home in Tampa

Entire Home Walking Distance to Downtown
Private house rentals

Tampa Bay Cozy apartment

Chic & Cozy stay -airport, beach & Raymond James

The Coastal Calm - Entire Unit

Cozy Hen House Retreat

The Palm Haus • Heated Pool • Near Beach • Games

Heated pool, hot tub, game room, 10 min to beach

HSE Bush Garden 20min/Tesla EV/15 min from Airport

Brand new Studio only 8mn away to Clearwater beach
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ712 | ﺩ.ﺇ775 | ﺩ.ﺇ731 | ﺩ.ﺇ654 | ﺩ.ﺇ617 | ﺩ.ﺇ606 | ﺩ.ﺇ643 | ﺩ.ﺇ643 | ﺩ.ﺇ617 | ﺩ.ﺇ668 | ﺩ.ﺇ698 | ﺩ.ﺇ683 |
| 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 |
Quick stats about house rentals in Oldsmar

Total vacation rentals
Explore 90 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 2,860 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with pools Oldsmar
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- Hotel rooms Oldsmar
- Rentals with a hot tub Oldsmar
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- Family-friendly rentals Oldsmar
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- Rentals with beach access Oldsmar
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