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

Stunning BEACH FRONT Condo, KING Size Bed, Balcony
NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach
Welcome to BELLEAIR BEACH OASIS! This luxuriously updated 2BR/1BA POOL HOME is minutes away from beaches and golf courses! Walking distance to Belleair grocery, coffee shops, restaurants and more. Enjoy the private and fully fenced resort-style outdoor living featuring: inground pool, modern pergola w/lounge chairs, grill, covered dining and relaxing hammock! You’ll love this quiet Belleair Bluffs neighborhood offering easy commute to St. Pete Clearwater and Tampa Airports, local hospitals, etc.

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
🌴 😎 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.

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent
Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

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.

Courtyard View - Steps From The Sand - Pool
We’re happy to announce that our property is open, fully operational, and in excellent condition after the recent hurricane. Book with confidence and enjoy your Florida getaway! No hidden fees or complicated check-out instructions. ☞ Free parking ☞ Pool ☞ AC ☞ Self check-in ☞ Full Kitchen Essentials (linen, towels, toiletries) are provided at the start of your stay. We recommend getting more supplies for extended stays. We are located on the beach at 3200 Gulf Blvd, Belleair Beach.

Waterfront Modern Chic #1 Clearwater Beach
This prime location is on the bay just steps away from the beach and the main strip offering a complete home experience. This spacious apartment is equipped with a full kitchen, washer/dryer, two full bathrooms, a large family room, dining area, access to the pool and two assigned parking spaces. A split floor plan ensures privacy, accommodating guests on either side of the apartment. The private patio overlooks the bay, offering stunning views of the sunrise and the occasional dolphin.

Luxury Beach Bungalow | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Triplex- heated pool, bikes, walk to beach,
☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

2 King Suites • Waterfront • Walk to Beach
Escape to Dock of the Bay! ✅ Two KING suites + sofa bed ✅ 5-minute walk to beach ✅ Waterfront views ✅ Full kitchen ✅ Heated pool & sun deck ✅ Beach gear & wagon ✅ Free parking! 🎵 Welcome to Dock of the Bay, a Clearwater Beach escape where each day starts with a fresh vibe. With bayfront views echoing “sittin’ on the dock of the bay…”, this serene spot is ideal for couples and families in a walkable location near the beach, Pier 60, shops, restaurants, and activities.

3 Bedroom Waterfront Paradise Sleeps 8
Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

Cozy Stylish Home w/ Heated Pool & Big Parking

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront Townhome w/Game Room & Boat Slip! Walk

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Swim-Out Bedrooms, Waterfall pool, Peace Place

Palm Paradise - Family Amenities+Central Location

The Oasis | Heated Pool - Arcades - Mini Golf

Luxury Oasis • Heated Salt Pool • Near Beaches
Condo rentals with a pool

Relax in a Newly Renovated Beach Front Paradise

COASTAL CHIC! Luxury Apartment with Oceanviews

Newly Reno Luxury Condo 30 Steps to Paradise

Heron's Hideaway- Studio by the bay!

Beachfront Condo with Centerline Sunsets

POOL VIEW IN A MODERN CONDO - Feel at Home

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Royal Orleans at Redington Beach ( Studio 203 )
Other vacation rentals with a pool

Largo Palms Duplex-2BR/2BA + Heated POOL Unit A

Avalon. Clearwater. Cozy condo. Pool view.

NEW! LaPlage - Centrally Located - Family Friendly

Awesome Condo in Clearwater, FL

Hannah’s beachside resort Saltwater Heated Pool

Clearwater Vacation Rental Condo/Heated Pool

Cozy Clearwater Condo close to beach

Tranquil "Ocean Breeze Retreat"
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $290 CAD | $360 CAD | $435 CAD | $335 CAD | $269 CAD | $283 CAD | $287 CAD | $241 CAD | $228 CAD | $267 CAD | $301 CAD | $297 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 Clearwater Beach

Total vacation rentals
Explore 1,040 vacation rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach vacation rentals start at $68 CAD per night before taxes and fees

Verified guest reviews
Over 38,180 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 230 rentals that welcome pets

Rentals with dedicated workspaces
560 properties have a dedicated workspace

Wifi availability
1,030 of Clearwater Beach vacation rentals include wifi access

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

4.7 Average rating
Clearwater Beach stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Apartment rentals Clearwater Beach
- Fitness-friendly rentals Clearwater Beach
- Beach condo rentals Clearwater Beach
- Rentals with a washer and dryer Clearwater Beach
- Villa rentals Clearwater Beach
- Aparthotel rentals Clearwater Beach
- Rentals with an accessible height toilet Clearwater Beach
- Beach house rentals Clearwater Beach
- Beachfront rentals Clearwater Beach
- Rentals with breakfast Clearwater Beach
- Rentals with a hot tub Clearwater Beach
- Cottage rentals Clearwater Beach
- Luxury rentals Clearwater Beach
- Rentals with a fireplace Clearwater Beach
- House rentals Clearwater Beach
- Waterfront rentals Clearwater Beach
- Rentals with an accessible height bed Clearwater Beach
- Rentals with outdoor seating Clearwater Beach
- Family-friendly rentals Clearwater Beach
- Pet-friendly rentals Clearwater Beach
- Rentals with beach access Clearwater Beach
- Rentals with an EV charger Clearwater Beach
- Bungalow rentals Clearwater Beach
- Rentals with a patio Clearwater Beach
- Boutique hotels Clearwater Beach
- Rentals with lake access Clearwater Beach
- Condo rentals Clearwater Beach
- Rentals with a firepit Clearwater Beach
- Hotel rooms Clearwater Beach
- Rentals with a kayak Clearwater Beach
- Townhouse rentals Clearwater Beach
- Rentals with pools Clearwater
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park




