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.

4.98 out of 5 average rating, 221 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 tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 291 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

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.

4.83 out of 5 average rating, 187 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."

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.

4.94 out of 5 average rating, 286 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

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, 236 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 may 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 vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.

4.96 out of 5 average rating, 205 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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, 414 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 serene beach scene at sunset, where the sky is filled with hues of orange and gold. The calm water reflects the vibrant sky, and footprints are visible in the fine sand leading along the shoreline.

4.96 out of 5 average rating, 139 reviews

Lovely family Villa Close to Beach

Welcome to Fiddlers Cove. We offer you a great vacation experience in a 2 bedroom, 2 bathroom apartment, 5 minute walk to Folly Field Beach. The apartment has everything you need. Fully equipped kitchen, toys, puzzles, highchair, booster, beach toys, and of course the ocean. **No need to buy bottles of water. We have a water purifier built into the kitchen sink. Bring your refillable water bottles and save. Enjoy the fresh ocean air and the sunset from the balcony.

5 out of 5 average rating, 107 reviews

Condo in Sea Pines

5 Star Location-Pool, Walk to Dining/Shops/Marina

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Apartment in Fripp Island

A well-appointed room features a queen bed with a light grey quilt. A kitchenette is visible in the background, equipped with modern appliances. Two stools are arranged at a small dining table. Soft lighting is provided by pendant lights and bedside lamps.

4.87 out of 5 average rating, 347 reviews

Cozy Sunsuite Fripp Island Resort- Steps to Beach!

Experience the perfect beach getaway on Fripp Island! This cozy 1st floor sunsuite is ideal for couples and families with young children, offering unparalleled convenience just steps away from the beach boardwalk. Enjoy easy close access to resort amenities like an Olympic pool, Arcade, Adults-Only pool with pool bar, tennis courts, and Beach Club restaurant for a memorable stay. Book now to receive up to Two Fripp Resort amenity cards included, a $110 value!

Superhost

4.85 out of 5 average rating, 151 reviews

Pool + Beach Views | Sauna | Indoor Pool

2 Minutes Walk to Beach - Escape to your very own paradise just steps away from the pristine white sands of the beach. Our beautifully appointed condo offers a luxurious and relaxing getaway with a stylish, modern interior design that is sure to impress. The spacious and open floor plan creates a bright and airy atmosphere that is perfect for lounging with loved ones, while the comfortable bedrooms provide a peaceful retreat for a restful night's sleep.

A light-filled living area features a cozy seating arrangement with a white sofa and a coffee table. The kitchen can be seen in the background, highlighting modern cabinetry and a casual dining setup. Natural textures are present through the woven rug and wood accents.

4.83 out of 5 average rating, 184 reviews

Easy Walk to the Beach ~ Sleeps 6! TWO bathrooms

5 minute walk to closest beach(with beach bar). 19 minute walk to Coligny beach! COME STAY at this charming beach-walk community! The pool is at the bottom of the stairs, 3/4 of a mile to Coligny circle with grocery store, shops, and restaurants. “COPPERTONE DAYS” features: 4 twin beds(memory foam), a master bedroom/master bath, laundry room, and a stocked kitchen+ highchair and a crib! We can usually accommodate early arrivals!

Popular amenities for Fripp Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Hilton Head Island

A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.

4.99 out of 5 average rating, 102 reviews

6 BR, Sleeps 26, Beach Time

Superhost

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.

Home in Fripp Island

4.8 out of 5 average rating, 25 reviews

Fripp Island Marsh Views Amenity Cards 3 King Beds

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

4.96 out of 5 average rating, 115 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 Beach/Pool Pass Included!

4.94 out of 5 average rating, 123 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

Home in Saint Helena Island

4.99 out of 5 average rating, 133 reviews

The Hampton House

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, 53 reviews

Charming Fripp Island Cottage Retreat

4.96 out of 5 average rating, 132 reviews

The front exterior of the house features a welcoming porch with a central decorative door and flanking windows. Flowering plants are suspended from the eaves, while well-maintained shrubs frame the entrance. A clear pathway leads to the door, inviting guests into the home.

Home in Bluffton

Encanto of the Lowcountry in Old Town Bluffton

Condo rentals with a pool

A spacious living area is featured with a comfortable gray sofa and a coffee table on a patterned rug. A ceiling fan is installed for airflow, and natural light enters through nearby windows. Decorative artwork and soft lamps add a welcoming touch to the space.

4.95 out of 5 average rating, 113 reviews

Quick Walk to Beach- 2BR/1BA - South Forest Beach

A welcoming living area features a large gray sectional sofa accompanied by two blue accent chairs. A round black coffee table is centered on a light gray area rug, while a wall-mounted image of boats adds a coastal touch. The kitchen is visible in the background.

4.84 out of 5 average rating, 126 reviews

Modern villa for vacation or remote work getaway!

A decorative bicycle wall art piece in soft mint green is displayed alongside a playful turtle motif. The bicycle features a white woven basket and artistic details, adding a coastal charm to the interior.

4.94 out of 5 average rating, 236 reviews

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway

4.98 out of 5 average rating, 159 reviews

A welcoming living room is presented with two spacious sofas arranged around a decorative area rug. A large TV is mounted on the wall, and natural light filters in through sliding glass doors that offer access to the private balcony with views of the pool and surrounding greenery.

Condo in Tybee Island

Bliss on Bay 2 Bed / 2 Bath Beachfront Condo

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, 131 reviews

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

Superhost

A modern living area features a comfortable gray sofa paired with colorful accent chairs. A coffee table sits atop a textured area rug, while large windows provide natural light. A dining table with chairs and a small balcony view enhances the inviting space.

4.82 out of 5 average rating, 186 reviews

Snowbirds & Family rates - just ask!

A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.

4.98 out of 5 average rating, 205 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

A stretch of sandy beach is depicted under a bright sky, featuring three blue umbrellas positioned over wooden lounge chairs. Gentle ocean waves are seen rolling onto the shore, and the sun reflects off the water, creating a serene coastal atmosphere.

4.97 out of 5 average rating, 210 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Other holiday rentals with a pool

Apartment in Hilton Head Island

A light-filled living area features a cream-colored sofa with decorative cushions, complemented by a round wooden coffee table. In the backdrop, a mirrored wall enhances the spacious feel, while a vibrant beach-themed artwork adds a touch of coastal charm.

4.89 out of 5 average rating, 36 reviews

First Floor - 50 Yards to Sand- Partial Oceanview

Condo in Saint Helena Island

A serene view features palm trees framing a well-kept pool area, with bright blue lounge chairs arranged nearby. The scene is complemented by a sandy path leading to the ocean, under a soft pastel sky during dusk.

5 out of 5 average rating, 6 reviews

Island Retreat-Gorgeous Condo w/ Pool/Ocean Views!

Apartment in Palmetto Dunes

A spacious living area features comfortable seating arrangements, including a cozy sectional sofa and armchairs. Large glass doors provide access to the balcony, with views of the outdoors. The room is bright, complemented by a flat-screen TV and decorative shelving.

5 out of 5 average rating, 38 reviews

#4203 Renovated/1BR/2BA/Direct Ocean Views/Sofa Bd

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

Cottage in Saint Helena Island

A charming two-story cottage is framed by vibrant palm trees and lush landscaping. A welcoming entryway is highlighted by a blue front door, leading up a set of wooden stairs. Sunshine illuminates the exterior, enhancing the coastal appeal of the home.

4.86 out of 5 average rating, 85 reviews

Saltwater Zen - A Fripp Island Oceanfront Retreat

Condo in Saint Helena Island

A light blue Adirondack chair is positioned on a balcony, offering views of a green lawn and the ocean in the distance. Palm trees frame the scene against a backdrop of clouds and an expansive sky.

5 out of 5 average rating, 31 reviews

Tidewater Shoals, Ocean View! Cards Available

4.96 out of 5 average rating, 83 reviews

A spacious living area is highlighted by a modern sectional sofa and a wooden coffee table. Industrial-style decor is present, including a large wall art piece resembling a vintage wheel. A dining table is visible alongside a well-equipped kitchen, all set beneath exposed wooden beams.

Apartment in Habersham

Near Pool Shops Restaurants~Prestigious Habersham!

A vibrant sunrise casts warm orange and yellow hues across the horizon, reflecting off the ocean's surface. Silhouettes of palm trees frame the scene, while the beachfront resort's pathways and amenities are visible in the foreground.