Vacation rentals with a pool in Clearwater Beach

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, 346 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!

4.91 out of 5 average rating, 204 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

4.97 out of 5 average rating, 153 reviews

Clearwater Gem! XL-Pool | Courts & More!.

Welcome to The Quazzi House, a private ½-acre tropical escape designed for fun, relaxation, and unforgettable memories. This unique 4BR / 3BA home features a 40-ft pool, private hot tub, pickleball & basketball court, and a spacious backyard perfect for families and groups. 📍 15 min to Clearwater Beach 📍 20 min to Tampa 📍 10 min to PIE Airport Ideal for large families or groups looking for an active, resort-style stay in sunny Fl! NO PARTIES — $1,000 fine & cleaning fee strictly enforced!

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

4.97 out of 5 average rating, 206 reviews

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, 183 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.

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!

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!

5.0 out of 5 average rating, 152 reviews

4.93 out of 5 average rating, 123 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

4.99 out of 5 average rating, 214 reviews

A panoramic view of the inter-coastal waterway features clear turquoise waters and a marina with multiple boat docks. The backdrop is formed by a skyline of Clearwater's buildings under a bright blue sky, framed by lush tropical vegetation.

Home in Clearwater Beach

Waterfront 4BR | Walk to Beach | Pool & Spa

This stunning 3 story 4BR/3BA townhome (built in 2017) blends luxury, comfort, & the perfect beach town vibe. 2 blocks from the world famous white sands of Clearwater Beach and directly on the intracoastal waterway, this home offers everything you need for an unforgettable Florida getaway. Pool and hot tub access! Ideal for families, couples, or groups of up to 10 guests looking for a premium vacation experience. Beaches, boating, biking, shops, food, drink & water fun all steps away!

4.98 out of 5 average rating, 237 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

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, 311 reviews

Sandy Feet Retreat

Enjoy your stay with STUNNING VIEWS from your Very Own Balcony! This home is Fully Equipped and designed for your convenience. The Master Suite overlooks the Intra-Coastal & has its own Jacuzzi tub w/ separate shower. This End Unit allows ample lighting throughout. Located directly across the street from the infamous Shephards, and just steps to the Sugary White Sand, Clearwater Beach is known for! Walking distance to several Restaurants, Bars, Shops, & Tourist Attractions!

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

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

4.84 out of 5 average rating, 171 reviews

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, 148 reviews

Popular amenities for Clearwater Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 147 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

4.97 out of 5 average rating, 258 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

A spacious outdoor area is highlighted by a large pool surrounded by a stone patio. A dining table with multiple chairs sits beneath a wooden pergola adorned with lights. Lush palm trees and an elevated deck complete the inviting ambiance of the space.

4.93 out of 5 average rating, 187 reviews

Poolside Palms Pool & Gameroom - Mins to the beach

4.9 out of 5 average rating, 187 reviews

Heated Pool & Spa • Pergola Swing

4.94 out of 5 average rating, 102 reviews

PVT Heated Pool + Spa + Game Room, Dream VacaHome

A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.

4.85 out of 5 average rating, 141 reviews

Heated Pool Home | Close to Clearwater Beach

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 180 reviews

Palm Oasis | Heated Pool | Near Beaches

4.92 out of 5 average rating, 173 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

Condo rentals with a pool

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

4.98 out of 5 average rating, 197 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

4.93 out of 5 average rating, 153 reviews

Condo in Indian Shores

Panoramic Gulf View Beachfront Condo

A cozy sitting area is featured on the private balcony, highlighted by a circular rattan chair adorned with soft cushions. Green plants provide a touch of nature, while water views and boats can be seen beyond the railing, enhancing the relaxing atmosphere.

4.99 out of 5 average rating, 147 reviews

Waterfront Condo | Steps to Clearwater Beach 2King

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, 215 reviews

4.96 out of 5 average rating, 102 reviews

Dockside~Waterfront~Walk to Beach~Central Location

4.99 out of 5 average rating, 231 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

Condo in Indian Rocks Beach

The image captures a view of the Splash Harbour Water Park and adjacent condo building. Bright colors of the water slides contrast with the greenery of palm trees. The inviting pool area is visible, surrounded by lounge chairs and scenic pathways.

Waterfront, Harbourside, Water Park, Beach, #6620

4.87 out of 5 average rating, 263 reviews

4.97 out of 5 average rating, 156 reviews

Condo in Clearwater

Spacious Key West Retreat, Fun 2 BR, Resort Pool

Other vacation rentals with a pool

4.99 out of 5 average rating, 133 reviews

Villa in Palm Harbor

Palm Haus • Heated Pool • Near Beach • Game Room

Apartment in Clearwater Beach

Mid-Century Modern #4 Waterfront Clearwater Beach

4.89 out of 5 average rating, 189 reviews

Superhost

Condo in Indian Rocks Beach

September Deals! Beach Front Penthouse!

4.88 out of 5 average rating, 50 reviews

4.95 out of 5 average rating, 57 reviews

A modern, two-story building features a clean white exterior and is framed by lush palm trees. The ground level showcases multiple garage doors, while the upper level includes balconies with decorative railings. A spacious brick-paved driveway leads to the front entrances.

Home in Clearwater Beach

Luxury on water & Steps to beach

4.96 out of 5 average rating, 57 reviews

Pickleball-BBall-Volley-Bocce, Pool & Bar Resort

Condo in Indian Rocks Beach

An open living area showcases large sliding glass doors with stunning ocean views. A comfortable seating arrangement features a dark leather couch and coordinating throw pillows. A modern ceiling fan hangs above, while a dining table is set with a centerpiece and blue accents.

Sea Side Sunsets Unit C

5.0 out of 5 average rating, 37 reviews

4.89 out of 5 average rating, 9 reviews

Clearwater Pool Oasis|3 BR|2 King Beds|Near Beach