Holiday rentals with a pool in Charleston

4.97 out of 5 average rating, 118 reviews

A modern three-story residence features a light blue exterior with a clean white facade. Tall windows allow ample natural light, while palm trees and low greenery enhance the entryway's welcoming presence. The front door is painted in a contrasting color, adding visual interest.

Home in Park Circle

Happy Stays-In Park Circle-Dtwn-CHS Beach

Welcome to a remarkable three-story residence in Park Circle! Featuring three large, professionally designed, colorful bedrooms, each with its ensuite bathroom, it offers comfort & privacy. With five Smart TVs, a 110-inch movie screen, Pacman Arcade, Ping Pong Table, Ring Toss, Grill & other fun games, entertainment abounds. Relax on porches, take in views from the porch swing or wraparound windows, & enjoy a green space for pets & kids. A gourmet market next door serves delightful food & drinks

ValueFamilyAir conditioning

4.88 out of 5 average rating, 171 reviews

Pleasant Place New Build + Pool Great for Families

Bring your family & enjoy our brand new 2020 built home minutes to downtown Charleston, only 6 miles from the beach! Pleasant Place is in the BEST location to top restaurants & activities. This lovely 2700sqft 4 BR 3 BA pleasantly sleeps 10 guests and has all the familiar comforts of home with a fenced-in pool oasis, on a quiet street within walking distance to the Ravenel bridge connecting you to the heart of Charleston. Just a few minutes drive to the best beaches. Bring the family, book now!

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Guest house in James Island

A bright pool area is surrounded by lush greenery and vibrant landscaping. The pool features a unique shape and inviting turquoise water. Comfortable seating is arranged nearby, with colorful chairs contrasting against the light-colored walls of the house and deck.

4.99 out of 5 average rating, 354 reviews

Salt of the Island Retreat w/ Pool on the Lake

Welcome to Salt of the Island Retreat! Tucked away on James Island and very conveniently located between Historic Downtown Charleston (10 minutes away) and Folly Beach (15 minutes away), this hidden gem is nestled on a 5 acre lake, immersed in a vibrant ecosystem! After visiting all of the eclectic charm that Charleston has to offer, head back to Salt of the Island Retreat and reconnect with nature. Enjoy the sunshine and a cold beverage poolside while you heal your soul with the simple things.

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5 out of 5 average rating, 173 reviews

Villa in James Island

Villa overlooking Charleston close to Folly Beach

Nestled in a bird sanctuary on an oak filled tidal creek lot with expansive porch views of Charleston harbor, come share a coffee with friends and family and watch a spectacular marsh morning sun rise. Located minutes to the famous "Edge of America" Folly Beach, beach chairs, coolers and towels are provided for an enjoyable beach excursion. Centrally located, you are a short trip to historical Charleston, James Island County Park Splash Zone, and neighboring barrier islands. Off street parking.

LocationFamilyComfort

4.97 out of 5 average rating, 188 reviews

Marshfront 5BD Oasis | Pool, Yard & Steps to Beach

🏝️ Private Marshfront 4BR/5BD/3.5BA Home with stunning views, saltwater pool, fenced yard, hammocks, grill & outdoor shower 📍Steps to the beach! 🛎️ Personalized concierge services by On The Coast Property Group (fees vary) • Grocery stocking • Decoration setup • Dining reservations • Private chefs • Transportation coordination • Boating/water excursions • Beach rentals • Sports equipment • Baby gear • Spa, fitness & wellness services • Event planning for celebrations/gatherings …& more!

ValueLocationQuiet

The exterior of a two-story home is shown, featuring light yellow siding and dark green shutters. A well-maintained front yard with manicured shrubs flanks the walkway. An American flag hangs from the front porch, and a driveway leads to a single-car garage.

4.93 out of 5 average rating, 128 reviews

Mount Pleasant oasis near beach with private pool!

Beautifully updated Mount Pleasant home with a pool! The home's perfectly located just a few short miles from the IOP beaches and a stone's throw from great shopping nearby. This house is the perfect spot for a family vacation or just a weekend away with friends as it offers 3 bedrooms (2 with queen beds and 1 with a king bed). You can enjoy a day at the beach (5 mins away), just relax by the pool, or swim laps in the endless pool system with a push of a button. LIC# ST260331 Bus# 20139685

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Superhost

Four images showcase the serene surroundings of the Marsh House Retreat. A cowboy pool offers a refreshing escape, surrounded by lounge chairs. Hammocks are shaded under trees, and string lights illuminate a cozy seating area. The dining space features a vibrant atmosphere with decorative lighting.

Home in North Charleston

4.94 out of 5 average rating, 108 reviews

Sonny's Marsh Shack - Cowboy Pool/Bikes/Firepit

🛏 Sleeps 8 | 🛁 2 Bathrooms | 🌿 Marshfront Oasis Key Highlights & Amenities: 🌾 Marsh Front on Noisette Creek – Peaceful, scenic views in every direction 🚲 Low-country Cruiser Bikes – Explore the neighborhood the charming, laid-back way 💦 Cowboy Pool – Cool off and unwind with stunning marsh views 🌴 Hammocks – Relax and soak in the Lowcountry breeze 🔥 Outdoor Firepit – Cozy evenings under the stars 🎯 Outdoor Games – Cornhole, Spikeball, Giant Connect 4 & Giant Jenga for all-ages fun

LocationFamilyBeach

4.95 out of 5 average rating, 179 reviews

A bright and airy living room features two large, comfortable couches arranged around a wooden coffee table. Large windows allow natural light to fill the space, while light-colored curtains add a soft touch. A cozy fireplace is situated beneath a wall-mounted TV.

Home in Seabrook Island

Beautiful 2BD/2BA Seabrook Island Villa

Enjoy beach living in this beautiful two bedroom, two bath villa! Just 23 miles from downtown Charleston, Seabrook is a gated, 2200 acre resort community with multiple luxury amenities. This end unit villa overlooks the 15th fairway on Crooked Oaks golf course, and is just steps away from a private pool available only to residents and guests of Live Oak Villas. Beach and pool access, Seabrook Island Beach Club, and dining with spectacular views of the ocean, are located only a mile away.

LocationFamilyAccess

A spacious deck features comfortable seating arrangements, including lounging sofas and wooden chairs. A coffee table rests between them, inviting relaxed gatherings. The expansive view reveals lush marshland, with the Intracoastal Waterway visible in the distance under a softly lit sky.

4.83 out of 5 average rating, 219 reviews

Heated Pool-Walk to Beach-Hot Tub-Walk to Beach!

Come enjoy the most stunning views on Folly! With four private patios, a Private heated Plunge pool, a hot tub, and plenty of area's to relax - all overlooking the quiet, serene marsh; you are able to see amazing wildlife all around you while in complex relaxation mode. With two king beds, two queen beds, a bunkbed and 3 full bathrooms - there should be plenty of room. Enjoy tons of games, Golf hitting bay, darts, ping pong , swings and kids play area! STR23-0364799CF LIC00726

LocationFamilyAccess

The exterior of the home features a welcoming entrance with a light green door and decorative ironwork. Flanking the door are two large windows that provide natural light to the front of the house. A small landscaped area surrounds the entrance, enhancing the curb appeal.

4.94 out of 5 average rating, 133 reviews

Pristine Townhouse - Beach, Charleston, Pool, Fun

Stylish home with the short term guest in mind. Wood floors throughout. Views onto live oaks, park, community pool (subject to HOA opening and closing) and tennis. Sun drenched courtyard. Close to beaches, downtown Charleston, Patriots Point, Shem Creek, Alhambra Hall, Pitt Street Bridge and more. 2 queen beds and the 3rd with a twin bed & trundle. Great location. Please read house rules before booking. STR LIC ST260069; BUS LIC BL-24-005711..

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Home in Cannonborough Elliotborough

A spacious living area is furnished with two white sofas and two armchairs, each adorned with teal cushions. A circular coffee table is centered on a patterned area rug, and artwork hangs on the dark walls. Natural light floods the room through large windows.

4.97 out of 5 average rating, 267 reviews

2500SF Downtown 1849 home w/ pool!

The perfect Oasis in the middle of the Peninsula... Come home to this 2,500 SF c.1849 historic property and take a dip in the pool after a long day walking around or relax and have a cocktail on the balcony. Walk out the door and explore Cannonborough-Elliotborough and some of the best restaurants the City has to offer. Off-street parking for 1-2 vehicles is provided, a rarity downtown. We are a legal City licensed short-term rental 2026 OP. 07096.

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Home in Cannonborough Elliotborough

4.94 out of 5 average rating, 379 reviews

Boho Bungalow | Private Oasis w. Plunge Pool

Escape to this enchanting brick cottage just moments from the harbor where historic charm meets modern comfort. Cozy up in the inviting living spaces with warm tones and exposed brick or relax in the private garden just outside. A charming bedroom awaits and you’ll adore the fully equipped kitchen perfect for intimate meals. Now featuring a brand-new dipping pool!

ValueFamilyDecor

Popular amenities for Charleston rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 143 reviews

The dining area features a natural wooden table set with bowls and elegant table settings. Surrounding the table are comfortable, light blue chairs. Soft lighting is provided by a modern fixture overhead. A view of the sunroom is visible through the archway, enhancing the space.

Home in Summerville

Share-in Dipity Refined 4 bedrooms pool not heated

FamilyValueKitchen

4.83 out of 5 average rating, 170 reviews

A private saltwater pool is surrounded by a spacious wooden deck, featuring five lounge chairs for sunbathing, a shaded table for six, and a grill for outdoor cooking. Lush greenery and palm trees create a tranquil setting, enhancing the outdoor retreat.

Home in Kiawah Island

Kiawah Island Home w/ Pool - 4 bedroom /4 bath

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The coastal house stands against a vibrant sunset, surrounded by lush palm trees. Two spacious decks with white railings invite relaxation. The driveway leads to an entrance that features soft lighting, enhancing the inviting exterior. The tranquil atmosphere is complemented by the natural beauty of the surroundings.

4.9 out of 5 average rating, 127 reviews

Ocean Views~Heated Pool~Hot Tub~Golf~4Bed~2Bunk Rm

ValueLocationCheckout

4.89 out of 5 average rating, 243 reviews

The open living area features a comfortable sofa and two patterned armchairs, positioned near large windows that allow natural light to fill the space. A wooden coffee table is centrally located, creating an inviting spot for relaxation and gathering.

Home in Seabrook Island

Beach House- 0.4 Miles from the Ocean STR25-000614

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A private in-ground pool is surrounded by a spacious patio area, featuring colorful chairs and a large umbrella over the outdoor dining set. Lush greenery and a decorative fence enhance the vibrant outdoor setting under a bright blue sky.

4.97 out of 5 average rating, 140 reviews

Renovated House w/ Pool, Sauna,Gym,Outdoor shower!

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An aerial view of a spacious beach home surrounded by lush greenery. The property includes a private pool and a patio area with lounge chairs. Multiple decks are visible, highlighting the layout of the building and outdoor space.

4.98 out of 5 average rating, 186 reviews

Red Sunsets | Luxury Furnishings | Pool & Elevator

ValueLocationBack garden

4.97 out of 5 average rating, 132 reviews

The entrance to the cottage is framed by lush greenery and features a welcoming blue door. Two white chairs are positioned on either side of the front steps, offering a cozy spot for relaxation. A flag hangs proudly above the entrance, enhancing the charming curb appeal.

Home in Isle of Palms

Luxury Coastal Cottage With Pool

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The backyard features a large saltwater pool, surrounded by a stone patio. Eight lounge chairs are positioned along the edges, and an outdoor shed is visible in the background. Sunlight streams through trees, creating a serene outdoor setting.

4.92 out of 5 average rating, 159 reviews

Coastal Cottage in Charming Old Mt Pleasant

LocationFamilySleep quality

Apartment rentals with a pool

4.92 out of 5 average rating, 156 reviews

2 Bedroom condo w/ Pool Steps to Front Beach IOP

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The image captures a serene view of the beach, framed by patches of soft sand and tall, green grasses. The water stretches out into the distance, meeting a clear blue sky. The tranquil scene invites relaxation and enjoyment of the coastal environment.

4.91 out of 5 average rating, 193 reviews

Key Lime Condo

LocationValueAir conditioning

4.96 out of 5 average rating, 179 reviews

A dining area features a round table set for four, complete with plates and utensils. A cozy living room with a large couch and armchairs is visible, along with a staircase leading to the upper level. Natural light floods the space through patio doors.

Apartment in Charleston

Cozy Coastal Crib near Downtown and the Beach!

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Superhost

A scenic view of the ocean is presented, with a sandy beach visible in the distance. Palm trees frame the foreground, while a pool area and adjacent building are situated nearby. The boardwalk extends toward the water, enhancing the coastal atmosphere.

4.82 out of 5 average rating, 522 reviews

Oceanfront Top Floor ☼ Beautiful Panoramic View!

LocationFamilyOutdoor spaces

4.97 out of 5 average rating, 269 reviews

A serene outdoor balcony features a round table surrounded by colorful chairs, offering expansive views of marshlands at sunset. The warm colors of the sky reflect on the water, creating a peaceful setting. Glass door access enhances the connection to the interior space.

Apartment in Charleston

Little Oak Love | 5 Minutes to Folly | Marsh View

ValueLocationBiking

Apartment in Seabrook Island

A screened porch offers a cozy seating arrangement with a light-colored sofa and a woven coffee table. Tropical plants and large windows provide natural light and a view of the surrounding landscape. A ceiling fan enhances airflow in this inviting space.

4.93 out of 5 average rating, 135 reviews

Beautifully Transformed Upper Level Deluxe Villa

FamilyValueIndoor spaces

4.93 out of 5 average rating, 107 reviews

A covered porch offers a serene view of the sunset over the marsh. Four wicker chairs with blue cushions are arranged around a white coffee table. Lush greenery is visible in the distance, while the water reflects the warm colors of the evening sky.

Apartment in Charleston

Folly Beach Condo - Marsh View - “Westview Too”

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A view from the balcony showcases the ocean and a private pier in the distance. A white table with a starfish decoration is positioned in the foreground, with greenery and walking paths leading to the beach visible below.

4.94 out of 5 average rating, 394 reviews

Stylish Ocean Front Sanctuary

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Other holiday rentals with a pool

5 out of 5 average rating, 38 reviews

Home in Hanahan

Coastal Charm Cottage - Pool + Waterfront Access

ValueFamilyLaundry

4.99 out of 5 average rating, 253 reviews

A bright living area features a comfortable sectional sofa and accent chairs. A large flat-screen TV is mounted on the wall above a dark wood console. Natural light floods the space through sliding glass doors, which open to a screened back porch.

Townhouse in Charleston

The Oasis (Charming, Close, Sleeps 5)

LocationFamilyLayout

4.98 out of 5 average rating, 50 reviews

Home in North Charleston

Pool & Hot Tub Retreat, Arcade, 85" TV, By Airport

ValueLocationBeach

Cottage in Mount Pleasant

5 out of 5 average rating, 12 reviews

Private Plantation-Style Retreat w/ Pool!

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4.98 out of 5 average rating, 92 reviews

Folly Oasis | Beachside Home w. Pool + Parking

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Guest house in Park Circle

A shaded outdoor seating area is furnished with a comfortable couch and chairs, surrounded by tropical plants. A flat-screen TV is mounted on the wall, while a dining table awaits nearby. The entrance door adds a touch of charm to the inviting space.

4.93 out of 5 average rating, 204 reviews

My Happy Place

ValueFamilyCheck-in

Home in Cannonborough Elliotborough

The exterior of a charming cottage features light blue siding, white shutters, and a welcoming front door painted in a soft turquoise. A palm tree stands prominently in the foreground, set against a clear blue sky, enhancing the inviting entryway.

4.99 out of 5 average rating, 74 reviews

Green Cottage – Private Casa Zoë Downtown Stay

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