
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, 3mi 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.

Spectacular beach to bay views from this resort.
Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

The T and C Club
Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

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.

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.

Private pool, steps to gulf, fishing, bike trails
Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

FREE Heated Pool & Spa l Book your Winter Vacation
Bring the whole family to paradise with plenty of room for fun! Enjoy a private heated saltwater pool 💦, nearby beaches 🏖️, and all the space you need in this 5-bedroom home 🏡. Enjoy amenities and games galore 🎯🎲! 📍 **Nearby Beaches:** 🌊 Crystal Beach – 10 min 🌴 Honeymoon Beach – 13 min 🌅 Sunset Beach – 20 min ☀️ Clearwater – 30 min *⚠️ Pool & spa are saltwater and heatable—pool up to 80°F, spa up to 104°F. Temps may vary due to weather.*

Ocean Breeze • Easy - Heated Pool Access
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. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

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

Literally: 15 steps to the Pool, GroundFloor Condo
Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

Private apartment perfectly located in Citrus park
A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

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

The Jungalow SOHO - Pool/Hot Tub

Villa Paradise

Tropical Getaway w/Heated Pool & King Beds

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Rooms with a Pool

Entire residential home, Tampa. 3/2, Pool.

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Downtown Dunedin B&B Casa w/ Heated Pool
Condo rentals with a pool

Amazing main floor condo at Avalon

Very cozy quality place close to Clearwater Beach.

Modern and Cozy Condo 6 Minutes from the Beach !

Bright and Spacious 1Bed/1Bath condo.

Tropical Beachfront Penthouse-Beach Cottages

Royal Orleans and Redington Beach ( Studio 203 )

Modern Waterfront Condo - Captivating Sunset Views

waterfront condo! Dolphins in the bay
Other vacation rentals with a pool

Wonderful Condo at Avalon - Fully Renovated

The Coastal Calm - Entire Unit

The Coastal Casita- Private Pool Home in Tampa, FL

Summer Escape – Pool, Downtown, Near Clearwater

Stylish NEW one bedroom condo Clearwater beach

Condo Conveniently located to Clearwater Beach

2 Bed 2 Bath Remodeled House Palm Harbor

❤Amazing Waterfront View/Near Downtown& Airport ☀🐬
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,777 GYD | G$45,746 GYD | G$46,999 GYD | G$41,777 GYD | G$43,239 GYD | G$41,359 GYD | G$41,359 GYD | G$42,195 GYD | G$36,346 GYD | G$40,942 GYD | G$42,404 GYD | G$41,777 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 90 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at G$4,178 GYD per night before taxes and fees

Verified guest reviews
Over 1,870 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 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!
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
- Hotel rooms Oldsmar
- Rentals with a fire pit Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a washer and dryer Oldsmar
- Rentals with beach access Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with a hot tub Oldsmar
- House rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- 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
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
- Busch Gardens
- The Don CeSar
- Gulfport Beach Recreation Area
- Lakewood National Golf Club




