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Vacation rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hilton Head Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Condo in Hilton Head Island

4.88 out of 5 average rating, 160 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Peaceful decor. Screened balcony. Furnished kitchen. Free use of WIFI, beach chairs/umbrella, gym, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore our sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

Oct 26 – Nov 2

Condo in Hilton Head Island

4.98 out of 5 average rating, 222 reviews

Ocean View Luxe! KING BED 65"TV Bar Pickleball GYM

Beachfront Building! Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot HGTV Featured Decorator Coastal Decor KING BED Expanded Bedroom 2 SmartTVs Private Balcony Beach Chairs, Umbrella, Boogie Boards, Ice Chest, Pool Noodles Full Kitchen Top Floor Elevator RESORT: No Resort Fees Huge Oceanfront Pool 2nd Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated/24 Hour Security Trolley Stop 4 Beach Boardwalks Bradley Beach

Nov 10 – 17

Condo in Hilton Head Island

4.85 out of 5 average rating, 155 reviews

Boardwalk to Beach, Hot Tub, 3 Pools and Tennis!

Welcome to our beautifully renovated family friendly villa within walking distance to the beach! The villa is located in a wonderful 24 hour gated community offering endless entertainment! The resort includes tennis courts, outdoor pools, pickleball, heated indoor pool, hot tub, sauna, fitness room, indoor track, volleyball, BBQ and picnic area, an onsite store and deli as well as easy access to Coco's Oceanfront Bar & Grill. There is so much to do on the resort you will never want to leave!

Oct 16 – 23

Condo in Hilton Head Island

4.89 out of 5 average rating, 151 reviews

Beachfront property with ocean/sunrise view!

Ocean sunrises from your private balcony! Steps to the beach! Newly renovated 1 Bed/1 Bath villa in a gated ocean community. New flooring throughout with new central air/heat. Nicely appointed, fully equipped and immaculate. Perfect for up to 4 guests. Boardwalk to beach. Outdoor pool/showers. 2 beach cruiser bicycles included. Easy walk to Coligny Plaza for many restaurants, shops, grocery, etc. Great golf courses, tennis, biking/hiking trails, boating/fishing, parks in area.

Dec 12 – 19

Condo in Hilton Head Island

4.88 out of 5 average rating, 194 reviews

Our Villa by the Sea

Enjoy our villa by the sea with a short board walk to one of the longest beaches in the US. Complementary beach accessories waiting for you. Relax on the balcony with the fresh ocean breeze and a peak of the ocean. Located on Hilton Head Beach & Tennis Resort, enjoy all of the amenities as our guest ... bar & grill on the beach, pool with ocean view, tennis courts, bike rentals, restaurant, and fitness center. Or just venture out and discover Hilton Head Island's beautiful attractions.

Dec 27 – Jan 3

Condo in Hilton Head Island

4.97 out of 5 average rating, 119 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**

Mar 11 – 18

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 274 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Location .. Location .. Location !!! Private guest suite with independent entrance from outside, total privacy, and complete amenities, queen bed and full bath (no kitchen). Just step outside - great water-front restaurants with live music, weekly fireworks during summer, bars, shops, outdoor pool and BBQ. Supermarkets and more restaurants in 10 minutes walking. Free shuttle from April till September, beach only 1.4 miles. Great golfing, biking, tennis, fishing and water sports.

Feb 1 – 8

Condo in Hilton Head Island

4.95 out of 5 average rating, 228 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled - just last year! Adorable beach front condo located in Hilton Head Beach and Tennis Resort. Watch and listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within the resort where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rentals, and a newly renovated gym. It's all here! 😊The 2024 getaway your been waiting for! 🏖️

Nov 8 – 15

Condo in Hilton Head Island

4.99 out of 5 average rating, 312 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.

Nov 29 – Dec 6

Condo in Hilton Head Island

4.92 out of 5 average rating, 101 reviews

Secluded 1st Floor Beach Getaway

Newly Remodeled - 2 Bedroom/2 Bath First Floor Villa in a Gated Community - less than a five minute walk through our complex to a private, natural beach! Everything you need to enjoy a relaxing, peaceful getaway and all that Hilton Head Island is famous for. Located in a beautiful, quiet community that offers 2 outdoor pools and one indoor pool that can be enjoyed year round. Come discover why this island has been voted the #1 best island in the United States!

Oct 30 – Nov 6

Condo in Hilton Head Island

4.98 out of 5 average rating, 180 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

Step into oceanfront comfort. This beautiful condo has all the comforts of home and is located in the heart of the south end of the island steps away to restaurants, shopping and the pristine Coligny beach. It’s the perfect place for a romantic beach getaway for 2. Upon entry you will see an incredible view of the ocean in this light and bright TOP floor Breakers condo.The condo is cleaned/managed by the local owner to ensure 100% satisfaction by my guests.

Nov 10 – 17

Condo in Hilton Head Island

4.99 out of 5 average rating, 144 reviews

Reno’d 1st floor walk to beach, pools pickleball

Welcome to our lovely renovated 1st floor unit in Fiddler's Cove. Perfect for a tennis, golf, biking or beach holiday! A 6-7 min walk to Folly Field beach via private beach access. 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.

Nov 11 – 18

Vacation rentals for every style

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Popular amenities for Hilton Head Island rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Hilton Head Island

4.97 out of 5 average rating, 107 reviews

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

Jan 24 – 31

Home in Hilton Head Island

4.96 out of 5 average rating, 121 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Sep 20 – 27

Home in Hilton Head Island

4.94 out of 5 average rating, 128 reviews

Spa/Fully Screened Heated Pool/Elevator/Fenced-79

Feb 24 – Mar 3

Home in Hilton Head Island

4.85 out of 5 average rating, 100 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Apr 22 – 29

Home in Hilton Head Island

4.85 out of 5 average rating, 204 reviews

Coastal Town Gallery House - live like a local!

Oct 1 – 8

Home in Hilton Head Island

4.89 out of 5 average rating, 107 reviews

Luxe & Fun Family Gem ~ Walk to Beach ~ Pool ~ BBQ

Mar 3 – 10

Home in Hilton Head Island

4.86 out of 5 average rating, 345 reviews

W2Beach*4TVsRokuAppleTV*Pets *WiFi*3King ßds*grill

Aug 27 – Sep 3

Home in Hilton Head Island

4.86 out of 5 average rating, 102 reviews

Blue Sky Villa: Beach/pets/golf/tennis/pickleball

Nov 1 – 8

Condo rentals with a pool

Condo in Hilton Head Island

4.96 out of 5 average rating, 104 reviews

Luxury Couples Retreat !

Feb 11 – 18

Condo in Hilton Head Island

4.87 out of 5 average rating, 447 reviews

(2) Renovated, beachfront complex w/3 restaurants!

May 8 – 15

Condo in Hilton Head Island

4.85 out of 5 average rating, 234 reviews

Charming Sea Pines Villa with View on Hilton Head

Oct 27 – Nov 3

Condo in Hilton Head Island

4.81 out of 5 average rating, 112 reviews

HILTON HEAD RESORT CONDO - NEWLY RENOVATED

Mar 6 – 13

Condo in Hilton Head Island

4.86 out of 5 average rating, 107 reviews

Relaxing and comfy condo with lots of amenities!

Dec 11 – 18

Condo in Hilton Head Island

4.88 out of 5 average rating, 104 reviews

Casa del Sol

Feb 21 – 28

Condo in Hilton Head Island

4.9 out of 5 average rating, 127 reviews

Coastal Comfort! Condo in beachfront resort.

Nov 20 – 27

Condo in Hilton Head Island

4.95 out of 5 average rating, 115 reviews

2nd row ocean - walk to beach and Salty Dog Cafe

Dec 22 – 29

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

Total rentals
4.8K properties
Rentals with dedicated workspaces
2.4K properties have a dedicated workspace
Pet-friendly rentals
670 properties allow pets
Family-friendly rentals
3.9K properties are a good fit for families
Total number of reviews
102K reviews
Nightly prices starting at
$10 before taxes and fees

Destinations to explore