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

5 star Tampa Pool Oasis 2
Fully renovated 3bed 2bath open concept home with beautiful pond view and brand new POOL! Luxurious Travertine floors and handscraped wood floors throughout the home and beautifully modern renovated bathrooms. Large county park just 75 steps from the front door featuring kids play areas, fitness trail, and basketball courts make this a great family friendly or long term place to stay. 15 minutes to Busch Gardens, 20 minutes to downtown Tampa, 40 minutes to Gulf beaches, 1hr 15 mins to Disney.

The Borough Riverside Retreat
Located on the Hillsborough River in the heart of Tampa. Stores, parks, restaurants and bars within walking distance. The private suite is smaller in size but warm and cozy, it has a queen bed with luxuries likens Jacuzzi tub, a Kitchenette with a mini fridge, microwave, toaster oven, , HD TV, Ice Cold A.C. and more. The property has a heated swim spa, firepit , swing area w/ hanging bed, hammock, fishing dock, outdoor shower, kayaks, Jon boat, bikes, lawn chairs to catch some rays and more..

Specious home W/ Heated Pool ! ! ! Great Location.
Cozy, spacious home 🏡 w/ heated swimming 🏊♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's w/ Sling & Roku. The big back patio has a swimming 🏊♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

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

Entire house in Tampa w/ Heated POOL!
Our home is a 3/2. You walk into a open space with the dining room, living room & bright kitchen. The 1st bedroom is the Master Bedroom, equipped with a full bathroom, spacious closet, King Size bed & full body mirror. The 2nd bedroom has a queen bed, closet space, decorated with touches of care & is right next to the bathroom. The 3rd bedroom has 2 twin beds, FL touch vibes & is steps away from the bathroom. Last but not least our beautiful backyard with your own private pool! Pool heated

Millers, BeOne Naturally Clothing Optional Premium
Relax in your birthday suit in a fun clothing-optional Paradise lakes Resort. Modern furniture sleeps up to 4 People with a King Size Bed and a leather sleeper sofa in living room with Memory Foam mattress. Full kitchen with refrigerator, oven range and microwave for cooking, coffee maker, washer and dryer for laundry, 2 TVs, and a bath tub for relaxing. The clubhouse 2 Swimming Pools, Hot Tub, events like Karaoke, Live Bands and more (fees vary by days of week). Thank you and enjoy!

Tiny House: Walk to coffee and dinner! TPA 12 min!
Cabana Haya is an adorable 200 sq foot TINY pool/guest house featuring a queen-sized memory foam mattress, mini split heat/ac unit, smart TV, large bathroom, kitchenette stocked with cups, dishes, a microwave, a Keurig, a single burner cook top and tiny deck for outdoor relaxation by the pool (not heated). Cabana Haya is located in Historic Seminole Heights just minutes to Raymond James Stadium, Amalie Arena, The Tampa Riverwalk, Busch Gardens, The MidFlorida Amp , and all thing Tampa

West Tampa Villa 2 With Pool Oasis- Near Stadium
Come enjoy this newly renovated apartment with a full kitchen. You will love it !! This apartment is clean, cozy and quite to have a wonderful vacation with the benefits of a private suite it comes with queen size bed, smart tv, wifi access, closet, iron and iron tablet, full size shower, hair dryer, desk, kitchen full with coffee maker, microwave. Full size fridge and with a beautiful pool to relax. The pool area is shared!!! The pool has no heating!!! hours 8:00am to 8:00 pm

Seminole Heights Riverside Paradise w/Pool
Whether you're traveling for business, seeking a FL adventure or a short getaway staycation, the stunning waterfront views, pool & incredible amenities with convenient proximity to downtown Tampa, airport & area attractions, the guesthouse at Isla de Dij is the perfect accommodation. You'll fall in love with the massive live oaks that line the brick paved streets, the glassy waters of the Hillsborough River and the brilliant sunsets that paint the evening sky.

Red Comfort Trip Private Jacuzzi, near Busch Gard
Welcome to Red Comfort Trip – Private Jacuzzi & Pool near Busch Gardens. This cozy and fully private guest suite offers your own entrance, a comfortable bedroom, living area, full bathroom, and a private patio where you can relax after a busy day in Tampa. You’ll also enjoy a private jacuzzi and access to a large shared pool, all in a quiet residential area just a few minutes’ drive from Busch Gardens, the Hard Rock Casino, and other main attractions.

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 Carrollwood rentals with a pool
House rentals with a pool

Hacienda Hideaway w/ heated pool

Villa Paradise

Sea Breeze

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

3/2, 3 miles to Busch Gar *Pool, Game,CoffeeBar*

your home close to everything

Tropical Getaway, Perfect Home & Great Location

Contemporary & Fully Updated Heated Pool Home
Condo rentals with a pool

Spacious 2/2 ResortStyle Condo near Downtown Tampa

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

Tropical Waterfront Escape

USF Moffitt, Advent Health, B. Gardens, Golfing!

Tampa Bay Waterfront Views Voted Best Sunsets

The Sea Turtle Suite 𓆉 Corner Unit with Bay Views

Rocky Point paradise

Luxury Blue Haven - Stunning Tampa Bay Views!
Other vacation rentals with a pool

Relax & Explore in a Private Pool Oasis

The Coastal Casita- Private Pool Home in Tampa, FL

NEW Cozy Family Retreat, Tampa: Private Pool Oasis

The Pelican Cove - guest house

Tampa Tropical-Saltwater Pool-10 Min to TPA

Wild&Rooted Micro Vacay|River Walk&Armature Works

Cozy condo with golf course views!

Hidden Cottage
When is the best time to visit Carrollwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $272 CAD | $307 CAD | $314 CAD | $294 CAD | $286 CAD | $316 CAD | $280 CAD | $283 CAD | $279 CAD | $280 CAD | $249 CAD | $266 CAD |
| 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 Carrollwood

Total vacation rentals
Explore 60 vacation rentals in Carrollwood

Nightly prices starting at
Carrollwood vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 2,360 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Carrollwood vacation rentals include wifi access

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

4.7 Average rating
Carrollwood stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with a firepit Carrollwood
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- Family-friendly rentals Carrollwood
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- Rentals with pools Hillsborough County
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- Rentals with pools United States
- Anna Maria Island
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Cortez Beach
- Vinoy Park
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Busch Gardens
- Don CeSar Hotel




