Vacation rentals in The Settlement

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Top-rated vacation rentals in The Settlement

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Guest favorite

Villa in St. John, U.S. Virgin Islands

5.0 out of 5 average rating, 125 reviews

Coral Bay Penthouse Gorgeous Tropical Island Views

Picturesque TRADEWINDS TERRACE is a penthouse sitting directly above Coral Bay's restaurants, bars, shops, and grocery/convenience stores. This uniquely designed round villa sits in a tropical setting on a hillside overlooking water and islands, providing a panoramic view for miles around. Conveniently located on a fully paved road (Rt. 108) immediately accessible to the main road (Rt. 10/Centerline) leading to St John island’s beaches & Virgin Islands National Park. EASY & free parking on site.

Feb 7 – 14

R7,314 ZAR per night

Guest favorite

Cottage in Central, U.S. Virgin Islands

4.99 out of 5 average rating, 132 reviews

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

Mar 2 – 9

R6,054 ZAR per night

Guest favorite

Villa in Anegada, British Virgin Islands

4.9 out of 5 average rating, 50 reviews

Loblolly Beach Cottages: GREEN (1 bedroom/1 bath)

Just renovated! *All reviews before 2021 are pre-renovations. The same Caribbean cottage charm, but now with beautiful modern amenities. Location is everything here. Step out of your cottage and into the sand at beautiful Loblolly Bay. We located on one of the most beautiful beaches and coral reefs in the Caribbean, (and on most days you will have it all to yourself). Snorkeling, relaxing, walking to Big Bamboo for a drink, stargazing, or taking an adventure tour. A private slice of heaven!

Aug 14 – 21

R4,212 ZAR per night

Guest favorite

Guesthouse in Coral Bay, U.S. Virgin Islands

4.96 out of 5 average rating, 140 reviews

Ocean Blue Cottage

Update: New mattress as of Fall 2022! Ocean Blue Cottage located in Upper Carolina, 400' above sea level, overlooking Coral Bay harbor, Bordeaux Mt, Carolina valley and a peek of the Caribbean Sea. 23 steps down from the road, it has a bedroom 9'x12', dining/kitchen area 6'x10', bathroom 3'x10', private outdoor shower 4'x5', deck 8'x4' with grill, furniture, umbrella. Pricing is $150 night. There’s also an $90 cleaning fee per reservation. 5 min drive to restaurants, 10 min to beaches.

Jul 28 – Aug 4

R3,316 ZAR per night

Guest favorite

Villa in Central, U.S. Virgin Islands

5.0 out of 5 average rating, 24 reviews

Mykonos- freshly built Greek Inspired Luxury Villa

Mykonos Villa- A Greek inspired Luxury Villa. This private property is located in one of the most sought after areas offering un interrupted breath taking views of St. John’s south shore. Conveniently located a short drive from Cruz Bays world class dining, shopping, and the entrance to the North Shore beaches. Our 2 level villa , 3 suite king bedrooms, fully equipped kitchen, living room, balconies, with elegant and modern decor gives a comfy luxury experience plus your own private pool

Feb 21 – 28

R20,915 ZAR per night

Guest favorite

Villa in Virgin Gorda, British Virgin Islands

4.97 out of 5 average rating, 78 reviews

Seascape Guest House, Leverick Bay, Virgin Gorda

Seascape Guest House is an exquisitely designed one bedroom villa on Virgin Gorda in the British Virgin Islands. Just completed, the spacious 650 SF villa is sustainably designed and features an open plan kitchen and living area with master bedroom and ensuite bathroom. The screened in patio and roof deck provide additional outdoor space to relax and take in the stunning ocean views. A short walk from all the amenities of Leverick Bay Resort, Seascape is a one of a kind BVI retreat.

Dec 9 – 16

R8,390 ZAR per night

Superhost

Cottage in Coral Bay, U.S. Virgin Islands

4.97 out of 5 average rating, 186 reviews

Little Spice: A Modern Tiny Cottage in Coral Bay

Come stay in your very own private tiny cottage in Coral Bay, on the quiet side of St. John! Little Spice is the perfect base camp for an active and adventurous couple interested in exploring the island. While the space is small, it definitely packs a BIG punch including a kitchenette, a/c, wifi, queen bed, full bath, valley views, and a completely private outside lounging space with a grill. And for the beach? Beach chairs, noodle floats and a cooler . What are you waiting for?!

Feb 9 – 16

R3,656 ZAR per night

Guest favorite

Cottage in Hansen Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 58 reviews

Milk Moon Cottage

Situated on the quiet and serene East End of St. John, Milk Moon Cottage is a private oasis overlooking the British Virgin Islands. The cottage features striking views, convenience to East End beaches, and plenty of amenities to make guests feel right at home. *** KEY FEATURES *** -Two bedroom, two bathroom home with air-conditioning throughout -Full-sized kitchen -Completely private pool -WiFi -Beach chairs, beach cooler with ice packs, & beach towels all provided

Mar 29 – Apr 5

R12,376 ZAR per night

Guest favorite

Apartment in Coral Bay, U.S. Virgin Islands

4.99 out of 5 average rating, 133 reviews

5*****AFFORDABLE LUXURY STUDIOW/ JEEP RENTAL AVAIL

5 ★★★★★ LUXURY AT AN AFFORDABLE PRICE In Coral Bay- the quiet side of St. John. Deluxe private entry studio w/ A/C, king size bed & kitchenette. 5 minute walk to restaurants, grocery stores, shopping. 220 degree view of the Bay from your covered deck -100 ft. above the Bay. Paved road & driveway. 4WD, Auto., Jeep Wrangler & Liberty for rent. Reserved beach space -East End (15-18 m. Dr.) Room Service Menu Avail. Race, religion, & LGBTQ friendly.

Sep 18 – 25

R2,992 ZAR per night

Guest favorite

Apartment in Cruz Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 100 reviews

Sieben Apartment * Pool* next to Hiking trails

Spacious Luxury 2 Bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both rooms have memory foam mattresses from Loom & Leaf. The master bedroom has 1 King bed with private bathroom, and the second bedroom can be set up as 2 Twin beds or 1 King bed. 10 min drive from Cruzbay, Restaurants and grocery Stores. Shared brand new Pool (4ft deep) with two other apartments. Shared BBQ by the Pool.

Oct 11 – 18

R6,618 ZAR per night

Guest favorite

Hut in Tortola, British Virgin Islands

4.94 out of 5 average rating, 134 reviews

Tiny Cozy Shack 8 minutes from Beef Island airport

Located in a breezy valley on the East End of Tortola overlooking Beef Island & Virgin Gorda. Nestled among boulders where you can enjoy the sun rise. Simple tiny room (8’x10’) with full size bed has a private bathroom + outdoor shower, no hot water.. Outdoor kitchenette with mini fridge, stove, kettle, toaster. Electricity, solar lights and WiFi available.

Dec 17 – 24

R1,983 ZAR per night

Superhost

Home in Virgin Island, U.S. Virgin Islands

4.78 out of 5 average rating, 213 reviews

Simplicity-affordable with a view

Simplicity is targeted at the down-to-earth traveler who comes to explore nature and simple living. It is a small studio with a kitchen, a bathroom, and a breathtaking view that is loved by our guests you can enjoy from the bedroom or the deck where you can relax with views of turquoise waters, green hillsides, and the neighboring British Virgin Islands.

Mar 24 – 31

R2,734 ZAR per night