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Vacation rentals with a pool in Hilton Head Island

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Vacation rentals for every style

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Popular amenities for Hilton Head Island rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favorite
Home in Hilton Head Island
5 out of 5 average rating, 77 reviews

98 Sandcastle Ct

Top guest favorite
A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.
Home in Sea Pines
5 out of 5 average rating, 19 reviews

Starfish Beach House with Pool and Bikes

Guest favorite
Home in Hilton Head Island
4.98 out of 5 average rating, 109 reviews

Resort-Style Pool, Cute House 88 Steps to Sand

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 Sea Pines
4.91 out of 5 average rating, 148 reviews

Water Views Treehouse walkable to Harbour Town

Guest favorite
The image showcases a backyard oasis featuring a newly constructed pool surrounded by a patio. Lounge chairs are arranged around the pool, and vibrant greenery enhances the tranquil setting. A shaded area with a table and umbrella is visible in the background.
Home in Hilton Head Island
4.98 out of 5 average rating, 90 reviews

Private pool/spa : pool heat available : Kg master

Guest favorite
The living area features an open layout with a cozy sofa and patterned armchairs surrounding a wooden coffee table. Natural light streams through large sliding glass doors that provide a view of the pool and outdoor seating area. Neutral tones and decorative accents create a welcoming environment.
Home in Hilton Head Island
4.95 out of 5 average rating, 20 reviews

Modern Serenity - Steps to Beach and Coligny Plaza

Guest favorite
Home in Hilton Head Island
4.86 out of 5 average rating, 372 reviews

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

Guest favorite
The spacious backyard features a large heated sports pool surrounded by a well-manicured lawn. Deck chairs in vibrant colors are arranged along the poolside, while a covered deck is accessible from the house. Lush trees provide shade, enhancing the relaxing outdoor environment.
Home in Sea Pines
5 out of 5 average rating, 5 reviews

Ask @ New Listing Discounts~Sea Pines~Pool~Yard

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Condo rentals with a pool

Guest favorite
An expansive beachside pool is featured, surrounded by lounge chairs positioned on a paved deck. The pool's clear water reflects the blue sky and nearby palm trees, creating a relaxing atmosphere. Umbrellas provide shaded seating areas, enhancing comfort for guests.
Condo in Hilton Head Island
4.93 out of 5 average rating, 57 reviews

1Min Walk to Beach/Ocean View Balcony/Huge Pool

Guest favorite
An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.
Condo in Hilton Head Island
4.89 out of 5 average rating, 197 reviews

Easy Breezy at Hilton Head Beach & Tennis

Guest favorite
The pool area is surrounded by lounge chairs and features a spacious pool with clear water. Tall palm trees provide shade, while the elegant building stands in the background under a clear blue sky. An umbrella is positioned for sun protection.
Condo in Palmetto Dunes
4.9 out of 5 average rating, 104 reviews

Luxury Condo King bed Pool &Ocean views hot Tub

Top guest favorite
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.
Condo in Hilton Head Island
4.97 out of 5 average rating, 116 reviews

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

Guest favorite
An aerial view captures the villa and surrounding area, highlighting the proximity to the beach. The ocean is visible in the background, while the spacious grounds feature multiple buildings and a parking area. Nearby greenery enhances the coastal atmosphere.
Condo in Hilton Head Island
4.93 out of 5 average rating, 130 reviews

Ocean View 1-bdrm. Steps to the Beach and Pool.

Guest favorite
A light-filled living area features a comfortable gray sofa and a white coffee table. A large television is positioned on a matching media console. In the background, a dining table for four is visible, with the kitchen seen through an open doorway.
Condo in Hilton Head Island
4.91 out of 5 average rating, 573 reviews

(4) Location! Walk to Coligny Beach Shops Dining!

Superhost
An expansive oceanview features a large swimming pool and spacious deck area surrounded by lounge chairs. The distant beach, with umbrellas dotting the sandy shore, is accessible via a wooden walkway. The clear blue sky complements the serene coastal landscape.
Condo in Hilton Head Island
4.86 out of 5 average rating, 116 reviews

Beautiful Ocean View- Top Floor - Beach & Tennis

Guest favorite
Condo in Hilton Head Island
5 out of 5 average rating, 72 reviews

THE SANDPIPER’s NEST Luxury direct Oceanfront

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Quick stats about vacation rentals with a pool in Hilton Head Island

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    R178 ZAR before taxes and fees

  • Total number of reviews

    120K reviews

  • Family-friendly rentals

    4.4K properties are a good fit for families

  • Pet-friendly rentals

    830 properties allow pets

  • Rentals with dedicated workspaces

    2.8K properties have a dedicated workspace

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