Vacation rentals with a pool in Clearwater

4.91 out of 5 average rating, 184 reviews

Heated Pool & Spa • Pergola Swing

"Peaceful pool/spa haven with a responsive host." That's how a guest described Viewtop, our single-story Clearwater pool home with a heated pool and spa, and a pergola hung with two porch swings. Coffee in the pergola swings at sunrise, a dip in the spa, a game of pool or a round on the arcade in the game room, dinner under the chandelier, then a movie on the 65-inch Roku. King master, two queens, a queen, and two queen sleeper sofas in the second living room. Eleven minutes to Clearwater Beach.

4.88 out of 5 average rating, 145 reviews

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

Lots to Love about this centrally located Clearwater beauty. This pool home is 25 minutes from the Tampa airport and 15 minutes to famous Clearwater Beach and less than a half hour to downtown St. Pete, not to mention a 10 minute walk to Phillies spring training stadium and minutes by car to hundreds of Shoppes and Restaurants. Enjoy this spacious home with split bedroom plan and brand new furnishings. Sweet dreams on the Casper mattresses. Relax Poolside in the screened lania or by the firepit

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 303 reviews

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!

4.99 out of 5 average rating, 128 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

4.91 out of 5 average rating, 200 reviews

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

4.98 out of 5 average rating, 181 reviews

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.

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 482 reviews

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.

4.94 out of 5 average rating, 116 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

4.98 out of 5 average rating, 234 reviews

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. 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

Townhouse in Clearwater Beach

The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.

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.

4.99 out of 5 average rating, 146 reviews

4.94 out of 5 average rating, 100 reviews

Just Wow! Luxury & Huge Heated Pool & Spa Home!

🏡 Bring the whole crew to a Clearwater retreat built for fun! 🎮 Newly added air-conditioned game room with pool, ping-pong, foosball, air hockey and a classic arcade cabinet. 🏊 Screened saltwater pool with built-in spa. 🌴 Fenced yard with cornhole, covered lanai and grill. 🛏️ This 5-bedroom, 3-bath home sleeps 16 and adds two living rooms, a full kitchen, WiFi, laundry and parking for four—all a short drive from Clearwater Beach and Indian Rocks Beach.

4.99 out of 5 average rating, 132 reviews

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!

Popular amenities for Clearwater rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 109 reviews

Star House! Heated&Salt pool/ Clearwater Beach

4.89 out of 5 average rating, 178 reviews

Family Retreat w/Pool, Outdoor Kitchen, Near Beach

A modern kitchen is presented with navy blue cabinetry and a spacious island featuring seating for four. Quartz countertops and stylish light fixtures add elegance. Natural light streams through a nearby window, illuminating the adjacent dining area with a table and chairs.

4.88 out of 5 average rating, 145 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

A vibrant pool area features playful tiger floaties and white spherical decorations floating on the surface. The pool is surrounded by comfortable lounge chairs and hammocks, with colorful drapes leading to the entrance of the house. Lush greenery and palm trees add a lively touch.

4.9 out of 5 average rating, 232 reviews

Clearwater GLAM | Pool, Games, Hot Pink Oasis!

The living area features a spacious white sofa and a complementary armchair set. A light wood coffee table sits on a neutral area rug. A large window provides natural light, and a ceiling fan adds to the bright, airy ambiance. A flat-screen TV is mounted on the wall.

4.88 out of 5 average rating, 100 reviews

Magnolia Pool House W/ Luxury Golf Cart

A heated pool area is surrounded by tropical plants and palm trees. A tiki hut provides shaded seating, and lounging chairs are positioned around the pool. A textured stone deck complements the inviting water of the pool, creating a relaxed atmosphere for guests.

4.9 out of 5 average rating, 128 reviews

Tiki House •Sleeps 12 •Walk to Beach + Heated Pool

4.94 out of 5 average rating, 120 reviews

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

Private pool, Golf Cart, Completely Renovated!

4.92 out of 5 average rating, 166 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

Condo rentals with a pool

4.97 out of 5 average rating, 155 reviews

Spacious Key West Retreat, Fun 2 BR, Resort Pool

A welcoming entrance to The Avalon features a landscaped roundabout with manicured greenery and vibrant flowering plants. A central fountain adds a serene element, while the building's architecture is framed by palm trees and blue skies.

4.95 out of 5 average rating, 112 reviews

Condo Conveniently located to Clearwater Beach

4.96 out of 5 average rating, 101 reviews

Dockside~Waterfront~Walk to Beach~Central Location

A scenic view of the Intra-Coastal Waterway features several boats docked along wooden piers, framed by palm trees. The clear blue water reflects the sky, while distant buildings line the shore, creating a tranquil coastal setting.

4.86 out of 5 average rating, 310 reviews

Sandy Feet Retreat

A wide view of Clearwater Beach showcases soft white sand lined with colorful umbrellas and beach towels. Bathers enjoy the warm waters where turquoise waves meet lighter green ones. In the background, beachgoers can be seen near the resorts and other structures along the shoreline.

4.94 out of 5 average rating, 136 reviews

Beach Haven in South Clearwater Beach

Superhost

The modern condominium complex features multiple balconies overlooking a pool area. Vibrant tropical plants surround the pool deck, which is equipped with lounge chairs and shaded umbrellas. Clear blue skies and palm trees add to the inviting outdoor space.

Condo in Treasure Island

Beachfront Condo Resort on Treasure Island

4.89 out of 5 average rating, 214 reviews

The spacious living area features a comfortable sectional couch and a gray recliner. A coffee table sits atop a decorative rug. Natural light enters through windows adorned with soft curtains. A dining table for six is positioned nearby, adding to the inviting atmosphere.

4.86 out of 5 average rating, 209 reviews

Charming Condo Minutes From Gorgeous Beaches

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 343 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Other vacation rentals with a pool

4.93 out of 5 average rating, 175 reviews

A living room features exposed wooden beams and a brick accent wall, enhancing the cozy environment. A flat-screen television is mounted on one wall, and a coffee table sits centrally on a patterned rug. A lounge sofa and a chair provide comfortable seating options.

Loft in Clearwater Beach

CWB Retreats at Baymont Lofts - Loft A

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

4.97 out of 5 average rating, 233 reviews

Townhouse in Clearwater Beach

A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.

Waterfront Beach House Steps Away from #1 Beach!

5.0 out of 5 average rating, 150 reviews

Apartment in Clearwater Beach

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

4.88 out of 5 average rating, 265 reviews

Superhost

A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.

Cottage in Clearwater Beach

Mermaid Cottage

4.84 out of 5 average rating, 170 reviews

Apartment in Clearwater Beach

A comfortable living room features two brown leather sofas facing a glass coffee table. Natural light fills the space through sliding glass doors that open to a balcony overlooking water. A TV is positioned on a stand, with coastal-themed artwork adorning the light green walls.

Parker Manor Water View 2 Br Apt 12

4.81 out of 5 average rating, 188 reviews

Bungalow in Indian Shores

A pool is situated in the foreground, with clear water reflecting sunlight. Beyond the pool, a patio is enclosed by a white railing, leading to a sandy beach and ocean. Lush palm trees provide shade, enhancing the indoor-outdoor living experience.

Private Beachfront 4BR 2BA Bungalow*Pool*PETS OK

4.96 out of 5 average rating, 187 reviews