
House holiday 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.

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!

Tree House Treasure
We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

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

Mins to Beach/Studio Home/walk to dwtn/FreeParking
✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.

My Little White Space .
My apartment is located an excellent position of access to different places of Tampa bay .Apartment with independent entrance.Near to: Tampa international airport-4miles Mall international plaza-4 miles Downtown Tampa 8.7 miles Raymond James stadium Beaches within 5 miles. NO CHILDREN OR PETS WILL BE ADMITTED.

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.

Modern & Spacious Retreat with Private Pool!
Welcome to our exquisite Airbnb in Oldsmar, Florida, where luxury and convenience converge in a SINGLE-story haven. This delightful getaway promises an unforgettable stay for travelers seeking relaxation, outdoor adventures, and a touch of historical charm.
Popular amenities for Oldsmar house rentals
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Tampa Getaway Pool Home

Villa Paradise

House of Relaxation

Dunedin 5 STAR+ Heated Pool+Near Beach

Tropical Getaway w/Heated Pool & King Beds

Rooms with a Pool

Heated SW Pool - Near Beaches, Golf, Trail & Food
Weekly house rentals

Tampa Bay Cozy apartment

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

Executive Home | Work + Play Made Easy in Tampa

The Coastal Calm - Entire Unit

MGD Lux: Near TPA, Clayman Thyroid Center.

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

Brand new Studio only 8mn away to Clearwater beach

Downtown | Pure Comfort | Dogs Welcome
Private house rentals

Chic & Cozy stay -airport, beach & Raymond James

Spacious 2/2 Villa w/ Air Purifier & Reading Nook

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

AeroLuz Your modern retreat.

Coastal cottage getaway! Beaches, Golf Cart Rental

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

2 Bed 2 Bath Remodeled House Palm Harbor

Serenity Bungalow Downtown
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $323 NZD | $351 NZD | $331 NZD | $296 NZD | $279 NZD | $274 NZD | $291 NZD | $291 NZD | $279 NZD | $303 NZD | $316 NZD | $309 NZD |
| 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 holiday rentals
Explore 90 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $50 NZD per night before taxes and fees

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

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a fire pit Oldsmar
- Fitness-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with beach access Oldsmar
- Rentals with pools Oldsmar
- Rentals with outdoor seating Oldsmar
- Hotel rooms Oldsmar
- Family-friendly rentals Oldsmar
- House rentals Pinellas County
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club
- Fred Howard Park




