Holiday rentals with a pool in Fripp Island

Condo in Saint Helena Island

The open-concept kitchen and dining area are visible, featuring dark cabinetry and a granite countertop. A dining table for four is positioned nearby, and stairs lead to the upper level. Soft blue walls complement the space, creating a calm atmosphere.

4.99 out of 5 average rating, 210 reviews

Turtle Villa|Ocean Front/New DECK; B Building

Take in the lush, coastal beauty of the Carolina Lowcountry from our 2BR/2.5BA Cedar Reef Villas condo! Watch the glow of sunrise on the marsh & ocean without leaving your plush king bed. Play a game of tennis, then take a cool dip in one of the resort's pools within walking distance. Stroll to the beach via the Cedar Reef boardwalk access, or drive 3 miles to pristine Hunting Island State Park. Close out the day in nearby Beaufort with a date night dinner and a stunning sunset on the marina!

A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.

4.96 out of 5 average rating, 318 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

A spacious kitchen featuring sleek white cabinetry and a large marble island with seating for four. Modern appliances, including a stainless steel refrigerator and oven, are visible, along with a stylish black backsplash that complements the overall design.

4.9 out of 5 average rating, 107 reviews

Luxe Hilton Head Beach Villa w/ Pool Views

Escape to our beautiful beach getaway where you are just a short walking distance to a beautiful natural beach. Our completely restored condo is designed with the perfect blend of luxury and relaxation to enjoy your time in Hilton Head. Our spacious and open floor plan creates a bright and an inviting atmosphere that is perfect for lounging with loved ones and friends. Our bedrooms will give you a perfect night of rest and relaxation while each bathroom provides the perfect spa like experience

4.98 out of 5 average rating, 185 reviews

A charming cottage is set amidst lush greenery, featuring a wide, welcoming pathway made of patterned pavers leading to a spacious deck. Large windows reflect natural light, and a few outdoor chairs are positioned under umbrellas, inviting relaxation in the shaded area.

Cottage in Beaufort

Private Island Cottage

Looking for a place to relax and enjoy a stress free holiday, consider this Beautiful cottage set on a private Island with dock access to the intercoastal water way. Minutes from downtown Beaufort, 35 miles from Hilton Head Island, 45 miles from Savannah, GA, 60 miles from Charelston. only minutes from great resturants and attractions like: Hunting Island state park and public golf coures. Fishing, kayaking or paddel boarding (equipment provided), or just relax on one of the docks or porches.

4.96 out of 5 average rating, 314 reviews

Ocean & Marsh View KING BED 65"TV Bar Pickleball

✨Top 5% Guest Favorite✨ 2-3 min walk to Beach Beachfront Building Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot! KING BED + Big SmartTVs HGTV Decorator Designed Coastal Decor Private Top Floor Balcony Beach Chairs + Ice Chest Provided Couples Retreat! Well designed 540 square foot condo RESORT: 4 Beach Boardwalks! Huge Oceanfront Pool Beachfront Bar & Grille Sports Bar 2nd Pool FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated w/24 Hour Security!!

Apartment in Hilton Head Island

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.82 out of 5 average rating, 177 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

Guesthouse in Saint Helena Island

The screened-in porch features a hanging bed adorned with colorful pillows and a soft blanket. Surrounding seating areas include patterned chairs and a decorative rug. Large windows provide views of the greenery outside, allowing natural light to illuminate the space.

4.99 out of 5 average rating, 233 reviews

Charming Waterfront Cottage with Beautiful Views.

This is a very comfortable guest cottage with one bedroom, bathroom with large shower, kitchenette, and living room. Guests will occasionally share the dock, screened-in porch, and swimming pool. A beach pass is provided for Hunting Island State Park as well as beach chairs and towels. "MarshSong" is an inspirational place for anyone who just wants to relax, or explore; a good central point for visiting Charleston and Savannah. Rest, relax, recharge - nap on a hanging bed; sleep well.

A view from the balcony captures the serene ocean and beach during sunset. Vibrant colors reflect across the water, while lush greenery and trees frame the picturesque scene. The elegance of natural beauty is enhanced by a lantern hanging nearby.

4.95 out of 5 average rating, 276 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your balcony. Natural beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!a

Apartment in Hilton Head Island

A comfortable living area features a beige sofa and a cozy chair, complemented by a decorative ottoman. Natural light illuminates the space from sliding glass doors leading to a patio, while serene artwork with ocean themes adorns the wall.

4.81 out of 5 average rating, 156 reviews

1st Floor Beach-Side Villa Resort

Welcome to our beautiful Hilton Head villa! This is a 2 bedroom, 2 bathroom 1st-floor villa in a quiet gated community located within a 5-minute walk from a beautiful beach with a private entrance. Parking for the villa is steps from the door, with shops & restaurants nearby. Perfect for family vacations, golf, and business trips. The gated community has 10 tennis courts, 2 large outdoor swimming pools, a hot tub, racquetball courts, fitness centers & playground. $100 late checkout fee

A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.

4.99 out of 5 average rating, 165 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

A bright and inviting living space features a gray sofa with decorative pillows and a white coffee table on a patterned rug. The modern kitchen showcases white cabinetry and a dining area with stools. Fresh flowers are arranged in a vase on the table.

4.99 out of 5 average rating, 402 reviews

Ocean Front Resort Condo

Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.

A renovated kitchen features modern stainless steel appliances including a microwave, oven, and dishwasher. White cabinetry and granite countertops create a clean aesthetic. Ample storage is provided by drawers and cabinets, while laminate flooring adds a warm touch to the space.

4.99 out of 5 average rating, 205 reviews

Coastal 1st Floor Condo walk to beach pools pball

Welcome to our newly renovated 1st floor unit in Fiddler's Cove. Perfect for a tennis, pickleball, golf, biking or beach holiday! A 5-7 min walk to Folly Field beach via a private beach access available to our guests. Use our beach gear. Great secure wifi. Surrounded by world class golf courses. Enjoy 5 star amenities including 2 pools, hot tub, racquetball, pickle ball courts and gym. Pools are open from march 1st-October 31st and hot tub remains open year round.

Popular amenities for Fripp Island rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 37 reviews

A spacious living area is furnished with a large brown leather sectional sofa and a wooden coffee table. Natural light floods in through multiple windows, showcasing lush greenery outside. A dining area with wicker chairs is visible, enhancing the open layout of the space.

Home in Pigeon Point

The '56 Retreat

4.95 out of 5 average rating, 111 reviews

A charming coastal cottage is surrounded by lush greenery and mature coastal foliage. The home features a spacious front porch with a bright blue front door, set against a backdrop of soft landscaping and a clear sky.

Home in Edisto Island

Sandpiper Dream - Walk To The Beach + Pool Access!

4.95 out of 5 average rating, 125 reviews

A spacious living area is accentuated by vaulted ceilings and large windows, allowing natural light to fill the room. Comfortable sofas are arranged around a central coffee table, with decorative cushions adding color. A lamp and a decorative vase create a welcoming ambiance in this inviting space.

Home in Palmetto Dunes

Lovely 3BR in Palmetto Dunes w/ new pool & spa

A spacious two-story home features a welcoming entrance, adorned with white railings and blue siding. The driveway leads to two brown garage doors, while lush green landscaping adds a touch of nature near the front. Sunlight highlights the architectural details of the house.

4.93 out of 5 average rating, 30 reviews

Fabulous 4 Bedroom 3 bath Home on Fripp Island, SC

4.94 out of 5 average rating, 121 reviews

An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.

Home in Palmetto Dunes

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

4.5 out of 5 average rating, 4 reviews

Tide Watch Oceanfront beach house at Harbor Island

Home in Hilton Head Island

4.75 out of 5 average rating, 4 reviews

Walk to beach - 2BD/2BA retreat

Home in Saint Helena Island

An open living area is highlighted by vaulted ceilings with wooden beams. A comfortable sofa faces a television, with a coffee table resting atop a soft area rug. The kitchen features modern appliances, and a dining table surrounded by chairs provides a cozy eating space.

4.94 out of 5 average rating, 50 reviews

Charming Fripp Island Cottage Retreat

Condo rentals with a pool

4.78 out of 5 average rating, 207 reviews

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN

5 out of 5 average rating, 107 reviews

A modern kitchen features a central island with a white marble countertop and two woven bar stools. Stainless steel appliances are visible, along with a stylish herringbone backsplash. Natural light highlights the clean lines and organized layout of the space.

Condo in Sea Pines

5 Star Location! Pool, Walk to Shops/Dining

The kitchen and dining area is equipped with modern appliances, including a microwave and coffee maker. A wooden table with six chairs is set for dining, while white cabinetry and light countertops create a spacious atmosphere. A sliding door provides access to the outdoor area.

4.97 out of 5 average rating, 100 reviews

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D

4.94 out of 5 average rating, 107 reviews

The living area is furnished with a spacious sectional sofa, accented by decorative pillows and a cozy throw. A large television is mounted on the wall, and floor-to-ceiling windows provide an ocean view, allowing natural light to fill the room.

Condo in Palmetto Dunes

Ocean Views at Villamare, Steps to the Beach!

A living area is characterized by a comfortable seating arrangement, featuring a light-colored sofa and a patterned armchair. A wooden coffee table is placed centrally, and a television is mounted above a decorative fireplace. Large windows provide views of the outdoor deck and surrounding greenery.

4.98 out of 5 average rating, 126 reviews

1BR/2BA condo w/private beach access in Shipyard

A bright kitchen and dining area is featured, showcasing light wooden cabinetry, stainless steel appliances, and a dining table with four chairs. A large flat-screen TV is mounted on the wall, and tasteful decor adds a cozy touch to the space. Natural light fills the room.

4.96 out of 5 average rating, 115 reviews

Beach Front Resort - Ocean View King Bed

A comfortable bedroom features a spacious bed adorned with white and blue striped bedding. Two bedside lamps provide gentle lighting beside the bed, while a large mirror reflects the room’s arrangement. Windows allow natural light to illuminate the space, highlighting the soft gray carpeting.

4.91 out of 5 average rating, 168 reviews

Beach condo in gated resort w/ tons of amenities!

A serene landscape is presented, featuring a tranquil pond surrounded by lush greenery and palm trees. The view extends toward the beach, with well-maintained walkways leading through the gardens. A clear sky with scattered clouds adds to the peaceful ambiance.

4.92 out of 5 average rating, 142 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Other holiday rentals with a pool

4.99 out of 5 average rating, 99 reviews

A spacious deck features a circular fire pit surrounded by four wooden adirondack chairs with cushions. A striped pouf adds comfort to the area. Scenic sunset views over the beachfront landscape create a serene backdrop.

Chalet in Sea Pines

180º Ocean Views, Treehouse "Siren's Lookout"

Lush vegetation lines the foreground, featuring tall palm trees and dense greenery. The expansive marsh area extends in the background, showcasing vibrant shades of green under a clear sky with scattered clouds, offering a serene natural view.

4.82 out of 5 average rating, 22 reviews

Fripp Island Marsh Views Amenity Cards 3 King Beds

The exterior of a split-level beach house is visible, featuring a light-colored facade with a spacious deck and stairs leading to the upper level. Lush greenery surrounds the property, and palm trees are positioned in the yard, adding to the coastal setting.

4.84 out of 5 average rating, 49 reviews

Private Pool-Fripp Island-Steps From The Beach

5 out of 5 average rating, 16 reviews

The open living area features a spacious sofa surrounded by two armchairs and a glass coffee table. A large artwork decorated with soothing colors hangs on the wall, and a ceiling fan is visible above, enhancing the relaxed ambiance.

Villa in Fripp Island

Tidal Treasure - Fripp

A welcoming living area features a cozy sofa and a round dining table, surrounded by yellow chairs. A stylish woven light fixture hangs above the table, while soft lighting from lamps creates a warm atmosphere. A sliding glass door allows natural light and leads to a patio.

4.96 out of 5 average rating, 70 reviews

Sea la Vie @ Fiddler's Cove

5 out of 5 average rating, 5 reviews

Home in Harbor Island

King Suite | Golf Cart | No Gate Fees | Park Pass

5 out of 5 average rating, 20 reviews

A serene view of calm waters features a distant sailboat gliding gracefully across the horizon. Lush greenery and tall grasses frame the scene, with a palm tree located in the foreground, offering a glimpse of the natural coastal landscape.

Treehouse in Sea Pines

Luxury Waterfront Tree House | Harbour Town | Pool