
Holiday rentals with a pool in Oldsmar
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oldsmar
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Coastal Escape: heated saltwater pool & beaches
â Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 â Heated saltwater pool â Screened-in lanai â BBQ grill â Large backyard w/ playground â Outdoor dining area â 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds â Renovated kitchen and bathrooms â Open living space - great for family gatherings, movie nights â Children toys and games

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach
đ´ đ Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach đââď¸ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach đ (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

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, 42â 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.

Private 1 Bed Apt with Pool and water front.
Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

Downtown Tampa Pool House! Walk to Armature Works!
Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

Modern Paradise home near Clearwater Dunedin Beach
Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

Tropical Oasis Retreat w/ Heated Pool
Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

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.

Rooms with a Pool
Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

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

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr
This stylish place featuring a heated pool upon request is perfect for groups, family vacation or work trip. Has an open layout nice kitchen all furniture and appliances brand new. We are walking distance to Lake Tarpon-Bring your boats and jet skiis! Honeymoon Island is 8.8 miles Tampa, Dunedin Causeway only 7.6 miles . Tarpon Springs sponge docks 5.8 miles .St. Pete & Clearwater beach are not to far by car.
Popular amenities for Oldsmar rentals with a pool
House rentals with a pool

Heated & Screened in Pool-All Essentials Provided

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

House of Relaxation

Private pool, Golf Cart, Completely Renovated!

The Palm Haus ⢠Heated Pool ⢠Near Beach ⢠Games

Tropical Getaway w/Heated Pool & King Beds

Luxurious House with private Pool.

Game Room, Heated Pool, 5 minutes to Beach
Condo rentals with a pool

Tropical Waterfront Escape

Very cozy quality condo close to Clearwater Beach

Bright and Spacious 1Bed/1Bath condo.

Rocky Point paradise

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

Amazing views on beachfront

Stunning Balcony Views â Your Sunny Escape Awaits!

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Other holiday rentals with a pool

Paradise by the Park

The Coastal Calm - Entire Unit

Sunny's Retreat

Colorful, Comfy Townhome - Community Swimming Pool

Boho 3BR/2BA Pool, Ping Pong, BBQ, FirePit Airport

Modern 2BR/2BA | King Bed + Pool, Gym #7

The Pelican Cove - guest house

Poolside Tiny Guesthouse â Palm Oasis
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $353Â NZD | $386Â NZD | $397Â NZD | $353Â NZD | $365Â NZD | $349Â NZD | $349Â NZD | $356Â NZD | $307Â NZD | $353Â NZD | $356Â NZD | $360Â 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 holiday rentals with a pool in Oldsmar

Total holiday rentals
Explore 80 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $35Â NZD per night before taxes and fees

Verified guest reviews
Over 1,930 verified reviews to help you choose

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

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 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 guestsâaveraging 4.8 out of 5!
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- Anna Maria Island
- John's Pass
- Raymond James Stadium
- Weeki Wachee Springs
- Busch Gardens Tampa Bay
- Dunedin Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- River Strand Golf and Country Club
- Adventure Island
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Busch Gardens
- Fred Howard Park