Holiday rentals with a pool in James 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!

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.

Daniel Island Studio For Your Enjoyment!

Finished Room over Garage in historic Charleston, SC, is a cozy and beautiful living space with a full bath and kitchen, as well as a washer/dryer. Conveniently located in Smythe Park, just a mile away from downtown Daniel Island with shops and grocery store (Publix). Approximately 20 - 25 minutes from downtown Charleston. Accessibility limitations: this space requires walking 16 steps to access, and there is not a grab bar in the bath. No pets, smoking, or partying please. Permit #00711

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.

Little Oak Love | 5 Minutes to Folly | Marsh Views

Little Oak Love is a serene escape just a mile from Folly Beach, nestled in a gated community. This top-floor, two-bedroom, two-bath condo offers stunning views from almost every room, and ultimate privacy. Sip your morning coffee or catch sunset views from the screened lanai or balcony. Enjoy access to the community pool, pavilion, gas grill & fire pit. Plus, you're only a 20-minute drive from historic Downtown Charleston. This condo is perfect for the ultimate Lowcountry vacation experience!

Folly River Walk Everywhere, Pool, and Dock

Enjoy laid back Folly Beach Lifestyle Walking distance from the beach, restaurants, and shops. 3 bedrooms each with its own bath make it the perfect space! Enjoy the community dock and pool! Inside the home the kitchen has been renovated and is a great open layout to enjoy friends and family. Ditch the cars once you arrive though! Walk, bike, or rent a golf cart for the week! Enjoy the best sunsets from the pool or dock after a day at the beach! *Please no animals due to family allergies*

CHS Golfview Guest house - Poolside Retreat

Stay at The Golfview Guest House, a peaceful 2BR, 1.5BA retreat on the 10th hole of Charleston’s award-winning Municipal Golf Course, “The Muni.” Enjoy a full kitchen, bright living area, and sleeping for four (1 queen, 2 twins). Relax by the pool or take in golf-course views in Riverland Terrace, one of Charleston’s most beloved neighborhoods. Just 10 min to downtown and 9 miles to Folly Beach, this spot offers privacy, comfort, and Southern charm — ideal for families, couples, or friends.

Amazing Views - hot tub - 5 beds - Walk to beach

**Pool will not be completed until June 2026. Our home offers some of the most stunning views on Folly! With four private patios, a Private heated Plunge pool and hot tub overlooking the 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

Indigo House Poolside Retreat

Indigo House Poolside Retreat is a bright, beachy & bohemian space that is perfect for your stay in beautiful Charleston! This one bedroom pool house apartment is located in the heart of James Island, just 10 minutes from the downtown peninsula and 15 minutes from Folly Beach. It can sleep up to four adults and includes a full kitchen with incredible outdoor space including a salt water pool and a gas fire pit. While the pool house is located in the owners' backyard, it feels very private.

Riverfront Retreat/2 Balconies Pool, Walk to Beach

Wake up to peaceful Folly River views, sip coffee from your private bedroom balcony, then stroll to the beach or downtown Folly in minutes. This beautifully renovated 2-bedroom 2 1/2 bath condo features two private balconies, sunset water views, pool access, and an unbeatable location — perfect for couples, friends, or small families looking for a relaxing coastal getaway • Minutes to downtown • Night walk safety • No parking stress • Bars/restaurants ***2.5 bathrooms for only 4 guests

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.

Luxury pool, center of Folly, 2 blocks to beach!

Luxuriate in the lagoon pool or large hot tub and listen to the ocean on this private dune. You CAN have it all: an intimate, luxurious, artsy, home on a hill above the Folly nightlife... 3 master bedrms/2 baths!) AND... ONLY 2 BLOCKS to Folly's center AND the beach.Unforgettable PORCH times! It's MASSIVE! ********One of the king beds/baths is an attached guest house. ***** Enjoy the sounds of the pool fountain and the walks to the pubs/restaurants!