Luxury Rentals in "Leeward"

From USD 2500 p/n

Solarah | 4BR

Caribbean Selection, Corporate Retreat, Villas, Wellness Collection, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Short Walk to the Beach

4

8

4

Leeward

From USD $ 3,000 /night

Villa Aqua Bliss

Adventure Vacations, Caribbean Selection, Golf Vacations, Ocean View, Villas, Wellness Collection, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Villa Near The Beach

4

8

4

Leeward

From USD $ 4,000 /night

The Catch

Beachfront Villas, Caribbean Selection, Corporate Retreat, Golf Vacations, Honeymoon Collection, Ocean View, Summer 2025, Villas, Yoga Retreat / Christmas & New Year Holidays 2025/2026

5

12

5.5

Grace Bay, Leeward

From USD 4000 p/night

Young Villa

Caribbean Selection, Corporate Retreat, Golf Vacations, Ocean View, Villas, Waterfront, Wellness Collection / Villa Near The Beach

7

14

7

Leeward

From USD 2200 p/night

Villa Rehab | 4 BR

Adventure Vacations, Caribbean Selection, Corporate Retreat, Golf Vacations, Ocean View, Villas, Waterfront / Christmas & New Year Holidays 2025/2026, Villa Near The Beach

4

8

5

Leeward

From USD 2200 p/night

Villa Rehab | 6 BR

Adventure Vacations, Caribbean Selection, Food & Wine Collection, Golf Vacations, Large Retreats, Ocean View, Villas, Waterfront / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Large Villas, Villa Near The Beach

6

12

5

Leeward

From USD 2186 p/night

Fully Staffed

Villa Azimuth

Caribbean Selection, Corporate Retreat, Golf Vacations, Honeymoon Collection, Ocean View, Villas, Waterfront / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Villa Near The Beach

3

6

3

Leeward

From USD 2800 p/night

7th Night Free

Aquazure

Adventure Vacations, Beachfront Villas, Caribbean Selection, Honeymoon Collection / Christmas & New Year Holidays 2025/2026

5

10

5

Leeward

From USD 2530 p/n

Villa Big Chill | 6 BR

Caribbean Selection, Corporate Retreat, Large Retreats, Ocean View, Villas, Wellness Collection, Yoga Retreat / Large Villas, Villa Near The Beach

6

12

6

Leeward

From USD 2250 p/n

Big Chill | 4 BR

Caribbean Selection / Christmas & New Year Holidays 2025/2026, Large Villas, Short Walk to the Beach

4

8

6

Leeward

From USD 1800 p/n

Solarah | 5 BR

Caribbean Selection, Corporate Retreat, Large Retreats, Ocean View, Villas / Christmas & New Year Holidays 2025/2026, Large Villas, Short Walk to the Beach

5

10

5

Leeward

From USD 17000 p/night

Fully Staffed

Sole e Mare | 10 BR

Beachfront Villas, Caribbean Selection, Corporate Retreat, Food & Wine Collection, Large Retreats, Ocean View, Villas, Wellness Collection, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Large Villas

10

20

10

Grace Bay, Leeward

From USD 2200 p/n

Below Deck | 5 BR

Adventure Vacations, Caribbean Selection, Golf Vacations, Large Retreats, Ocean View, Special Rates, Villas, Waterfront / Large Villas, Villa Near The Beach

5

10

4

Leeward

From USD 6950 p/n

5th Night Free

Fully Staffed

Cabuya | 5 BR

Adventure Vacations, Beachfront Villas, Caribbean Selection, Corporate Retreat, Large Retreats, Ocean View, Villas, Wellness Collection, Yoga Retreat / Fully Staffed Villas, Large Villas

5

10

5.5

Leeward

From USD 3200 p/night

Sunset Bay

Adventure Vacations, Caribbean Selection, Golf Vacations, Large Retreats, Ocean View, Villas, Waterfront / Christmas & New Year Holidays 2025/2026, Large Villas, Villa Near The Beach

8

16

7

Leeward

From USD 1500 p/n

7th Night Free

Sugar Apple

Caribbean Selection, Corporate Retreat, Food & Wine Collection, Golf Vacations, Ocean View, Villas / Christmas & New Year Holidays 2025/2026, Villa Near The Beach

4

8

4

Leeward

From USD $ 6,890 p/night /night

5th Night Free

Fully Staffed

Cabuya | 6 BR

Adventure Vacations, Beachfront Villas, Caribbean Selection, Large Retreats, Ocean View, Villas, Wellness Collection, Yoga Retreat / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Large Villas

6

12

6.5

Leeward

Starting From $ 7,700 /night

Fully Staffed

Amazing Grace

Adventure Vacations, Caribbean Selection, Corporate Retreat, Food & Wine Collection, Golf Vacations, Large Retreats, Ocean View, Villas, Wellness Collection / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Large Villas

5

10

5

Leeward