Holiday rentals with a pool in Sullivan's Island

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!

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!

2 Bedroom condo w/ Pool Steps to Front Beach IOP

Oceanside Villas A103 This newly renovated 2-bedroom, 2-bath first-floor condo is perfect for families, couples, or friends looking for a relaxing beach getaway. Located on the Isle of Palms strip in the Oceanside Villas community, this condo is just across the street from the beach and within walking distance of restaurants, shops, and local attractions. Enjoy a modern, clean, and bright space with access to a community pool, private pier & private beach access w/shared laundry facilities.

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.

Key Lime Condo

Located in the Front Beach district of Isle of Palms, about one block from the beach and right in the middle of all the fun. Walk to all Front Beach restaurants and bars including Papi's Taqueria, Coda del Pesce, and the world-famous Windjammer. Guests can enjoy the condo pool and plenty of free on-site parking. There are 16 units in this converted beach hotel. All are individually owned. Pandemic Info: The unit has its own HVAC system so you won't be sharing "air" with anyone. :)

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

Summer Hayes on IOP with extra special Pool

Enjoy Summer Hayes, our special 4-bedroom and 2-bath beach home! Its perfect for two small families or one large family. We bought this home in Oct 2016 and use it regularly and upgrade it constantly. Its a 2-minute walk to the beach, the beds sleep great and the kitchen is well equipped. The beach at 8th Ave will be the highlight of your trip. The evenings are quiet and the waves can be heard from our deck. Pool is not heated ... heated hot tub included free in Fall/Winter!

Renovated Home Near Shem Creek & Sullivan’s Island

Located in the heart of Old Village, this beautifully decorated 3-bedroom, 2-bath home is just 3 miles from Sullivan’s Island beaches and 5 miles to downtown Charleston. Walk or rent a golf cart to Shem Creek’s bars, restaurants, and The Post House. Ample parking and close to top Mt. Pleasant eateries. Clean, cozy, and welcoming – ideal for beach lovers, foodies, and history buffs. Must be 25+ to rent. Golf cart rentals available nearby. ST260053 BL-24-000027

Luxury Coastal Cottage With Pool

Experience Life in The Lowcountry! Our Coastal Cottage has luxury finishes, a gourmet kitchen, spacious bedrooms, and the new pool installed Spring of 2022 is ideal for discerning travelers of all ages. We pride ourselves on making sure your vacation time is special. Isle of Palms offers a premier beach vacation experience with pleasant beaches and delightful restaurants. We are a 5-minute walk to the beach on a quiet residential street away from the crowds.

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..

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.

SALTY HUT AT THE BEACH, Isle of Palms, SC

Hitch a ride from the airport and never need a car. This newly renovated cozy cottage will truly give you the Low Country beach experience you're looking for. Located on Isle of Palms and steps away from the nearest beach access. Walk to the grocery store or take a short walk down the beach to several restaurants & beachfront bars offering local live music. Tired of the beach, no problem. Simply walk to the community pool and tennis court.