
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.

Waterfront Townhome w/Game Room & Boat Slip! Walk
PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Beach, dolphin/manatee sightings, fishing, sunsets
Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and heated pool. Visit nearby restaurants, John's Pass Boardwalk and live music.

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

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach
Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Waterfront Beach House Steps Away from #1 Beach!
Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Amazing views on beachfront
This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

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!

Beachfront Condo in Exclusive Resort
The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Walk to beach (1 block), pool, putt putt, triplex
☀ 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

Watch the Sunrise at Sunrise! @ Clearwater home.
Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

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

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

[Guest Favourite] Family Fun Getaway | Heated Pool

Modern Pet-Friendly Beach House w/ Heated Pool & S

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

The Palm Haus • Heated Pool • Near Beach • Games

Hannah’s beachside resort Saltwater Heated Pool

3 BR/2B pool home WiFI and Brand new furnishings

Splash House - Relaxation Haven/Private Pool
Condo rentals with a pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

"Jewel At The Shores" Gulf Front, sleeps 5

COASTAL CHIC! Luxury Apartment with Oceanviews

Newly Reno Luxury Condo 30 Steps to Paradise

Beach Across the St | No Stairs |Parking in Front!

Modern and Cozy Condo 6 Minutes from the Beach !

Beachfront Condo with Centerline Sunsets

Beach Front Madeira Beach
Other vacation rentals with a pool

Balay Clearwater: Heated Pool, Grill, 15 min Beach

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

Clearwater Mediterranean Retreat • Pool & Fire Pit

Clearwater Calling in North Clearwater Beach

Gulf Front w Beach Access Condo

Waterfront Pool Home Fishing Dock Walk To Beach

Luxury on water & Steps to beach

Walk to Beach | Private Pool • Mini Golf • Firepit
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $294 CAD | $365 CAD | $441 CAD | $340 CAD | $273 CAD | $287 CAD | $291 CAD | $244 CAD | $232 CAD | $229 CAD | $253 CAD | $273 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 1,070 vacation rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach vacation rentals start at $69 CAD per night before taxes and fees

Verified guest reviews
Over 40,930 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wifi availability
1,070 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
- Beach condo rentals Clearwater Beach
- Aparthotel rentals Clearwater Beach
- Rentals with outdoor seating Clearwater Beach
- Apartment rentals Clearwater Beach
- Cottage rentals Clearwater Beach
- Rentals with an EV charger Clearwater Beach
- Villa rentals Clearwater Beach
- Rentals with an accessible height toilet Clearwater Beach
- Condo rentals Clearwater Beach
- House rentals Clearwater Beach
- Rentals with a sauna Clearwater Beach
- Waterfront rentals Clearwater Beach
- Rentals with a firepit Clearwater Beach
- Fitness-friendly rentals Clearwater Beach
- Bungalow rentals Clearwater Beach
- Rentals with a hot tub Clearwater Beach
- Family-friendly rentals Clearwater Beach
- Rentals with beach access Clearwater Beach
- Rentals with a washer and dryer Clearwater Beach
- Rentals with a fireplace Clearwater Beach
- Rentals with a kayak Clearwater Beach
- Rentals with an accessible height bed Clearwater Beach
- Beachfront rentals Clearwater Beach
- Rentals with lake access Clearwater Beach
- Rentals with a patio Clearwater Beach
- Townhouse rentals Clearwater Beach
- Luxury rentals Clearwater Beach
- Rentals with breakfast Clearwater Beach
- Hotel rooms Clearwater Beach
- Pet-friendly rentals Clearwater Beach
- Boutique hotels Clearwater Beach
- Beach house rentals Clearwater Beach
- Rentals with pools Clearwater
- 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
- Lido Key Beach
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- The Don CeSar




