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Vacation rentals with a pool in Hilton Head

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

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Popular amenities for Hilton Head rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favorite
A private pool measuring 25x14 feet is surrounded by a landscaped area and lounge chairs. The upper level of the cottage is visible, featuring a balcony with an American flag. Paved walkways and greenery enhance the outdoor space.
Home in Hilton Head Island
5 out of 5 average rating, 9 reviews

2nd Row - Private Pool ~ 4 King Bedrooms

Guest favorite
A private heated pool is presented with crystal-clear water, surrounded by a deck featuring four lounge chairs. The pool area is framed by lush greenery and trees, creating a peaceful outdoor space for relaxation.
Home in Hilton Head Island
4.96 out of 5 average rating, 90 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

Top guest favorite
The living room features a contemporary layout with two comfortable sofas and cozy accent chairs arranged around a central round coffee table. A large television is mounted above a media console, complemented by decorative plants and coastal artwork on the walls.
Home in Hilton Head Island
5 out of 5 average rating, 7 reviews

Walk to Beach, 8BR, Heated Pool, Sauna, Elevator

Guest favorite
A scenic outdoor dining area features two high white chairs and a small table, offering a view of the marsh and water beyond. The surrounding greenery includes palm and pine trees, creating a tranquil atmosphere.
Home in Hilton Head Island
4.91 out of 5 average rating, 150 reviews

Water Views Treehouse walkable to Harbour Town

Guest favorite
Home in Hilton Head Island
4.86 out of 5 average rating, 374 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

Guest favorite
A screened-in pool area features a clear blue pool surrounded by light-colored tiles. Comfortable lounge chairs are arranged nearby, and a dining set is positioned under a ceiling fan. A television is mounted on the wall for entertainment.
Home in Hilton Head Island
4.97 out of 5 average rating, 117 reviews

Cozy beach house w/Private Heated Pool near park

Guest favorite
A large outdoor swimming pool is surrounded by a landscaped area, featuring several lounge chairs arranged on a sun deck. Umbrellas provide shade over some seating areas, and the pool area is framed by greenery, offering a serene atmosphere for relaxation.
Home in Hilton Head Island
4.97 out of 5 average rating, 149 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Guest favorite
Aerial view of a private backyard featuring a kidney-shaped pool surrounded by a natural stone patio. Comfortable lounge chairs are positioned by the pool, and a covered area with overhead beams houses an outdoor kitchen. A fenced perimeter ensures privacy.
Home in Hilton Head Island
5 out of 5 average rating, 34 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

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Condo rentals with a pool

Superhost
An outdoor pool is surrounded by landscaped grounds, featuring lounge chairs positioned around the edges. A small gazebo is visible in the background, with tall trees providing shade nearby. The pool depth is indicated, showing a gradual slope with a shallow area marked at 3 feet.
Condo in Hilton Head Island
4.85 out of 5 average rating, 123 reviews

Modern villa for vacation or remote work getaway!

Guest favorite
Condo in Hilton Head Island
4.95 out of 5 average rating, 133 reviews

Heron Hideaway: lovely updated near-beach 2bd/2ba

Guest favorite
The spacious beachside pool is prominently featured alongside the sandy shore, offering sun loungers and shaded seating areas. The ocean's gentle waves meet the horizon under a clear blue sky, with beach umbrellas dotting the coast in the distance.
Condo in Hilton Head Island
4.71 out of 5 average rating, 231 reviews

Condo on Beachfront Resort

Top guest favorite
The spacious outdoor pool area is surrounded by lounge chairs arranged neatly along the perimeter. Lush palm trees provide subtle greenery in the background, while buildings of the resort stand at a distance against a clear blue sky.
Condo in Hilton Head Island
4.98 out of 5 average rating, 202 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Guest favorite
A large outdoor pool is surrounded by numerous lounge chairs and features a spacious area for swimming. People are enjoying the water under a clear blue sky, with grassy areas and shaded cabanas in the background, along with the condo buildings lining the edge.
Condo in Hilton Head Island
4.89 out of 5 average rating, 215 reviews

Oceanside Beach Retreat

Guest favorite
A large outdoor pool is surrounded by lounge chairs, providing ample space for relaxation. Palm trees and lush greenery frame the area, while a multi-story building can be seen in the background, contributing to the welcoming ambiance of the space.
Condo in Hilton Head Island
4.92 out of 5 average rating, 106 reviews

BEACH PATH At Hilton Head Beach and Tennis Resort

Top guest favorite
A spacious outdoor pool is surrounded by lounge chairs and umbrellas, with palm trees visible in the background. The clear water reflects the sky, creating a serene environment for relaxation. The area offers direct views of the beach beyond the pool.
Condo in Hilton Head Island
4.92 out of 5 average rating, 134 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Guest favorite
A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.
Condo in Hilton Head Island
4.84 out of 5 average rating, 166 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

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Other vacation rentals with a pool

Top guest favorite
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.
Apartment in Hilton Head Island
5 out of 5 average rating, 32 reviews

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

Top guest favorite
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 Hilton Head Island
4.99 out of 5 average rating, 90 reviews

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

Top guest favorite
An inviting open-concept living area features a dining table set for four, complemented by a soft rug beneath. A modern kitchen is visible in the background, with sleek cabinetry and appliances, while a comfortable seating area showcases a leather sofa and glass coffee table, illuminated by ceiling fans.
Condo in Hilton Head Island
5 out of 5 average rating, 21 reviews

Luxurious, Dog Friendly Ground Fl Villa Fazio Golf

Guest favorite
A table is set with two elegant glasses of white wine, a lit candle in a silver holder, and a champagne bucket containing three bottles. The background features a soft sunset over the ocean, enhancing a tranquil dining atmosphere on the private balcony.
Condo in Hilton Head Island
4.98 out of 5 average rating, 52 reviews

Direct Oceanview-Balcony-2MIN Walk Beach, 2 Pools

Top guest favorite
A cozy living area is highlighted by a round glass table atop a soft rug. Large sliding glass doors allow natural light to fill the space and provide a view of the blue sky and surrounding greenery. A wicker lamp and throw pillows add to the inviting decor.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 34 reviews

Oceanfront Villa with pool

Top guest favorite
A dining area features a reclaimed wood table surrounded by cross-back chairs. A shelving unit holds decorative items and books. Natural light brightens the stylish living room in the background, where plush seating and tasteful decor can be seen.
Home in Hilton Head Island
5 out of 5 average rating, 18 reviews

Steps to the Beach - Perfect All-Season Getaway

Top guest favorite
A circular window seat is framed by a decorative arch and surrounded by bookshelves filled with various books and decorative items. Plush cushions invite relaxation, while natural light filters through the stained glass window, offering a view of the outdoor greenery.
Home in Savannah
5 out of 5 average rating, 82 reviews

Casula Solis

Top guest favorite
Condo in Hilton Head Island
5 out of 5 average rating, 37 reviews

Palmetto Dunes! Luxe 2B Beach Golf Pickleball Pool

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