
Vacation 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.

2 BR/2 BA Key West Retreat, A+Pool, 3m to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (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.

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.

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.

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).

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

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.

By the POOL, Ground floor, King bed, NO PETS
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

red comfort trip" 5 minutes to Bush gardens
Welcome to Red Confort Trip, your private getaway in Tampa! Enjoy a fully private space with your own patio to relax or smoke in peace. Guests also have access to a lush shared backyard featuring a large pool, pergola, BBQ area, and a variety of fruit trees, flowers, and plants. Perfect for nature lovers! The backyard is shared with the owner and guests from another Airbnb, but each unit has its own private patio for those who prefer quiet time

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

Tranquil poolside guesthouse on the river
The apartment is on the Hillsborough River surrounded by nature but only 3 minutes away from the great restaurants, bars and breweries of Seminole Heights. It is walking distance to Lowry Park Zoo and park. Spot the beautiful Florida wildlife up close from the river dock. Soak in the outdoor pool surrounded by mature live oaks or take a canoe out on the river. Top beaches are 35 minutes by car. Great for a couple or a small family.
Popular amenities for Oldsmar rentals with a pool
House rentals with a pool

Paradise by the Park

The Coastal Calm - Entire Unit

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Villa Paradise

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

House of Relaxation

Clearwater Escape • Pool • Spa • Pet Friendly

Magnolia Pool House W/ Luxury Golf Cart
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

Very cozy quality condo close to Clearwater Beach

Rocky Point paradise

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

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

Tampa Bay Gem - Spectacular Beachfront Views

SHEEK and Glam- heated pool Updated! 3 mi to beach

Steps to Beach, Pool, Spacious 2/2, King Bed
Other vacation rentals with a pool

Colorful, Comfy Townhome - Community Swimming Pool

Stylish 2BR/2BA w/ Pool, Gym Near Airport #3

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

Private pool, Golf Cart, Completely Renovated!

The Palm Haus • Heated Pool • Near Beach • Games

2 Bed 2 Bath Remodeled House Palm Harbor

The Pelican Cove - guest house

Poolside Tiny Guesthouse – 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 | G$41,812 GYD | G$45,785 GYD | G$47,039 GYD | G$41,812 GYD | G$43,276 GYD | G$41,394 GYD | G$41,812 GYD | G$40,767 GYD | G$40,767 GYD | G$41,394 GYD | G$42,231 GYD | G$42,649 GYD |
| 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 vacation rentals with a pool in Oldsmar

Total vacation rentals
Explore 80 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at G$4,181 GYD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

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