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Vacation rentals with a pool in Hilton Head

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Top-rated rentals with a pool in Hilton Head

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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.)

Dec 22 – 29

G$23,990 GYD per night

Condo in Hilton Head Island

4.93 out of 5 average rating, 165 reviews

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

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

Mar 11 – 18

G$34,654 GYD per night

Condo in Hilton Head Island

4.97 out of 5 average rating, 209 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 private balcony. Private 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!

Dec 2 – 9

G$32,097 GYD per night

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

G$35,113 GYD per night

Condo in Hilton Head Island

4.97 out of 5 average rating, 199 reviews

HHBT Resort-OceanView-Remodeled-Steps to beach!

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!

Oct 22 – 29

G$35,242 GYD per night

Condo in Hilton Head Island

4.96 out of 5 average rating, 105 reviews

Beautiful Couples Retreat !

Welcome to Serenity by the Shore. Escape to this top floor unit which is steps away to the beautiful ocean. Our condo features a heavenly pillowtop mattress in the master bedroom, private ocean view balcony and fully equipped kitchen for all your cooking needs. The condo is perfectly located within the Hilton Head Beach and Tennis Resort, the island's largest ocean front pool, tennis courts, Pool Bar & Grill. This luxury condo is great for a solo getaway, family vacation or romantic escape!

Feb 3 – 10

G$29,475 GYD per night

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 24 – 31

G$25,454 GYD per night

Condo in Hilton Head Island

4.97 out of 5 average rating, 120 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**

Jan 1 – 8

G$48,535 GYD per night

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 275 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.

Aug 11 – 18

G$32,613 GYD per night

Condo in Hilton Head Island

4.89 out of 5 average rating, 167 reviews

Hilton Head Island - Beach Retreat !!

Newly painted 3rd fl. 2 BR/2 Bath walk-up (2.5 short flights of stairs) unit, new kitchen floor & carpet. Sleeps 6. A total of 5 beds includes 1 king, 1 twin bed, twin over full/bunk beds & a sofa bed. Fully equip. kitchen w/new appliances. Unit has an open fl. plan w/view of lagoon & fountain. 5 min walk across the parking lot to the beach. Coconutz Sports Bar & Jamaica Joez Beach Bar on site. Gym & Laundry room on premises. Resort Parking Pass Fee is $35.00 per vehicle.

Mar 29 – Apr 5

G$24,254 GYD per night

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.

Apr 10 – 17

G$38,338 GYD per night

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

G$33,268 GYD per night

Vacation rentals for every style

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Popular amenities for Hilton Head rentals with a pool

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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

G$103,624 GYD per night

Home in Hilton Head Island

4.85 out of 5 average rating, 100 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Feb 11 – 18

G$103,071 GYD per night

Home in Hilton Head Island

4.92 out of 5 average rating, 169 reviews

Spa/Fully Screened Heated Pool/Elevator/Fenced-51

Oct 16 – 23

G$178,847 GYD per night

Home in Hilton Head Island

4.96 out of 5 average rating, 121 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Aug 18 – 25

G$61,380 GYD per night

Home in Hilton Head Island

4.86 out of 5 average rating, 345 reviews

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

Mar 27 – Apr 3

G$88,310 GYD per night

Home in Hilton Head Island

4.86 out of 5 average rating, 102 reviews

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

Oct 25 – Nov 1

G$66,476 GYD per night

Home in Hilton Head Island

4.89 out of 5 average rating, 107 reviews

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

Oct 6 – 13

G$137,991 GYD per night

Home in Hilton Head Island

4.85 out of 5 average rating, 204 reviews

Coastal Town Gallery House - live like a local!

Apr 4 – 11

G$115,619 GYD per night

Condo rentals with a pool

Condo in Hilton Head Island

4.81 out of 5 average rating, 112 reviews

HILTON HEAD RESORT CONDO - NEWLY RENOVATED

Nov 3 – 10

G$26,338 GYD per night

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Nov 13 – 20

G$26,667 GYD per night

Condo in Hilton Head Island

4.97 out of 5 average rating, 155 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Jan 16 – 23

G$36,280 GYD per night

Condo in Hilton Head Island

4.98 out of 5 average rating, 181 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

Jan 7 – 14

G$45,861 GYD per night

Condo in Hilton Head Island

4.89 out of 5 average rating, 108 reviews

Pool + Beach Views | Sauna | Indoor Pool

Nov 12 – 19

G$32,886 GYD per night

Condo in Hilton Head Island

4.81 out of 5 average rating, 143 reviews

SeaForever-King Bed, Ocean Views w/ Beach Access

Dec 19 – 26

G$25,116 GYD per night

Condo in Hilton Head Island

4.92 out of 5 average rating, 102 reviews

Secluded 1st Floor Beach Getaway

Oct 18 – 25

G$36,296 GYD per night

Condo in Hilton Head Island

4.9 out of 5 average rating, 127 reviews

Coastal Comfort! Condo in beachfront resort.

Feb 13 – 20

G$31,181 GYD per night

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