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Holiday rentals in Lower South Hill

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Top-rated holiday rentals in Lower South Hill

Guests agree: these stays are highly rated for location, cleanliness and more.

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Cottage in Sandy Ground, Anguilla

4.8 out of 5 average rating, 10 reviews

Tranquil Cottage With Sea Views-North Hill Village

Welcome to Villa Kaiae in Anguilla, British West Indies. Villa Kaiae offers a relaxed setting just for two. The one-bedroom Anguilla villa is perched on the ridge at North Hill overlooking Road Bay harbor and offers stunning views of the Caribbean Sea, the surrounding islands, nightly tropical sunsets, and the quaint village of Sandy Ground below. Villa Kaiae offers you privacy to truly rediscover your senses and really get away from the daily grind. A rental car is needed if you decide to stay

8–15 May

$229 SGD per night

Guest favourite

Apartment in Meads Bay, Anguilla

5.0 out of 5 average rating, 7 reviews

Beach Resort 1 Bedroom Condo with Terrace, Hot Tub & Ocean View

Tranquility Beach Anguilla is Anguilla’s newest beach resort on top-rated Meads Bay Beach on the West End and was voted Best Boutique Hotel in Anguilla 2023. Everything you need for an ultimate beach vacation is at your doorstep and our award-winning staff is at your service. Swim and snorkel in turquoise waters. Walk to resorts, spas and top restaurants. This unit is professionally managed by our friendly resort staff including property manager, concierge team, housekeepers and beach butlers.

17–24 Oct

$612 SGD per night

Guest favourite

Apartment in Lower South Hill, Anguilla

5.0 out of 5 average rating, 19 reviews

Spacious 2nd FL Studio - 3 min to Rendezvous Bay

Enjoy your stay at this brand-new modern studio with high-end finishings throughout! Merrivale is located less than 3 minutes from Rendezvous Bay beach. This supersized studio accommodates up to 2 persons, with a workstation, a private patio, walk-in closet, and has everything to make you feel at home – free WiFi, Netflix, central air conditioning, washer and dryer, well-equipped full-sized kitchen, and tableware. A relaxing space to unwind, Merrivale is only minutes away from everything!

15–22 Dec

$303 SGD per night

Guest favourite

Home in Island Harbour, Anguilla

5.0 out of 5 average rating, 5 reviews

Oceanfront Villa With Pool Jacuzzi Near Shoal Bay

Your 2 bedroom oceanfront villa includes a private pool, hot tub & breathtaking caribbean views of Scilly Cay, Island Harbor. 5 minute drive to Shoal Bay. One of a kind sunrises from oceanfront terraces. Wake up to endless Caribbean turquoise views from the master King Bed. Relax on the spacious lower and upper decks . Take a dip in the pool or sea. Outdoor shower. Access additional club pool, common area and fire pit. Perfect for a family or romantic getaway. Welcome to Arawak Beach Villa.

3–10 Oct

$515 SGD per night

Guest favourite

Flat in West end , Anguilla

4.91 out of 5 average rating, 65 reviews

James Hughes nice place in West end

James Hughes apartment located in West end affordable and comfortable. we are close to maundays Bay Beach, shoal Bay West Beach, Barnes Bay beach, meads Bay Beach. we are also close to best buy supermarket. close to picante restaurants. excellent wifi. we have cars for rent $30per day we only take cash. we will take you back to the ferry or airport for free. Electric bikes for rent $25 per day. we also have scooters for rent $25 per day. we can take you to the beaches and pick you up $30

24 Nov – 1 Dec

$162 SGD per night

Guest favourite

Guest suite in West End, Anguilla

4.94 out of 5 average rating, 50 reviews

Hummingbird, Charming Garden Studio, West End

Stylish, cool yet affordable accommodations in a fabulous location. EXCELLENT WIFI. Unbeatable value for lovers of Anguilla's West End! Safe for singles - romantic for couples - all welcome. Walk to beaches: Mead's, Barnes and Maunday's Bays & places like Four Season's & Picante. Beautiful indoor/outdoor kitchen/lounge area &tropical garden. Discounts for long stay. You must be VACCINATED to vacation in Anguilla. Please visit the Anguilla Tourist Board for current entry protocols.

24–31 Mar

$246 SGD per night

Guest favourite

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 171 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

5–12 Oct

$416 SGD per night

Guest favourite

Loft in Marigot, St. Martin

4.99 out of 5 average rating, 116 reviews

Sea Loft Stunning View - Private Pool

* 200m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with sun loungers, garden furniture, outdoor table and BBQ * Office area * Wifi 100 Mbps * TV with thousands of channels from around the world * 250m walk to Fort Louis de Marigot Marina * 5 min walk to the city center of Marigot with its restaurants, shops and other shops * 5 min from the pier for St. Barts and Anguilla, and the taxi station

23–30 Apr

$587 SGD per night

Home in Sandy Ground, Anguilla

4.86 out of 5 average rating, 14 reviews

Helena’s Cottage

Your search for the perfect vacation beach home is over. Get ready to sink your toes into soft white sand just a few steps from the front door. You have found a special Gem on the island. What makes this Gem so special? First, it is hidden between the historic Road Bay Salt Pond and a beautiful white sandy beach. It is also located near the party spot and some of the best bars and restaurants on the island.

23–30 Apr

$157 SGD per night

Guest favourite

Flat in George Hill, Anguilla

5.0 out of 5 average rating, 12 reviews

Modern Smart Suite-1 bdrm studio w/ free fast WIFI

Little Lux- Smart Suite Studio offers savvy singles or couples an opportunity to live a little luxurious in a stylish modern setting with integrated smart technology, guests can unwind and disconnect and still remain connected. It's perfect for a weekend getaway or workful week. Private entrance, keyless access, and some touchless amenities make living up to new hygiene standards- easier.

19–26 Sep

$127 SGD per night

Guest favourite

Cottage in Cul-de-Sac, St. Martin

4.98 out of 5 average rating, 101 reviews

VILLA JADE 2: WATERFRONT/ POOL

VILLA JADE is a complex of 3 villas located in the CUL DE SAC Bay and its islets ... VILLA JADE 2 is a spacious suite /sea view for 2 people on the waterfront, with private pool. The 3 villas are adjoining but very quiet and intimate. Your only view is the sea... Direct access to the sea by a pontoon, and kayaks at your disposal.

3–10 Sep

$366 SGD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

12–19 Oct

$623 SGD per night

Holiday rentals for every style

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Popular amenities for Lower South Hill holiday rentals

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Air conditioning

Other great holiday rentals in Lower South Hill

Guest favourite

Flat in Grand-Case, St. Martin

5.0 out of 5 average rating, 10 reviews

Charming appartment on the beach, 1 or 2 bedrooms

30 May – 6 Jun

$452 SGD per night

Guest favourite

Flat in The Quarter, Anguilla

5.0 out of 5 average rating, 22 reviews

Thrush Nest View Studio Apartment

11–18 Jun

$169 SGD per night

Home in Shoal Bay Village, Anguilla

4.92 out of 5 average rating, 13 reviews

Shoal Bay Coastal Sanctuary, Anguilla

17–24 Apr

$931 SGD per night

Guest favourite

Flat in Grand-Case, St. Martin

4.92 out of 5 average rating, 74 reviews

lovely 1 bedroom beach front property

30 Oct – 6 Nov

$162 SGD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 36 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

22–29 Jun

$1,365 SGD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 56 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

19–26 Feb

$1,191 SGD per night

Guest favourite

Guest suite in The Valley, Anguilla

4.91 out of 5 average rating, 23 reviews

Hidden Treasure

21–28 May

$198 SGD per night

Guest favourite

Villa in Collectivity of Saint Martin, St. Martin

5.0 out of 5 average rating, 39 reviews

VILLA I LOVE View-villa luxe avec vue mer

12–19 Feb

$752 SGD per night

Destinations to explore