Holiday rentals with a pool in Road Town

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Road Town

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Villa in Coral Bay, U.S. Virgin Islands

4.93 out of 5 average rating, 85 reviews

Heaven's Gate - Spectacular Panoramic Ocean View

This Mediterranean style, four bedroom luxury villa sits at the top of a mountainside overlooking St. John’s pristine Hurricane Hole, designated a Virgin Islands Coral Reef Monument in 2001. Heaven’s Gate is a serene and very private hilltop vacation villa. Each of the four handsomely furnished bedroom suites includes its own private bath, three with outside showers, and each suite has access to outside terraces. Please review the House Rules prior to booking. Compliance is mandatory.

10 – 17 Oct

$8,819 AUD total

Guest favourite

Villa in Ballast Bay, British Virgin Islands

4.91 out of 5 average rating, 43 reviews

Villa Almondeen- Peaceful 2bedroom villa with pool

Villa Almondeen sits about 100 feet from the water’s edge in a private and secured area. It is five minutes away from the popular Cane Garden Bay Beach and 15 minutes from other close-by beaches. You can enjoy views of Jost Van Dyke and the boating activities around the “Bay.” To the left is an area called “The Pointe,” a line-fishing and snorkeling area, and to the right is the famous “Smith’s Toe (pronounced “Smittoe”), another fishing area, and home to the blue parrot fish.

10 – 17 Mar

$7,226 AUD total

Superhost

Apartment in Tortola, British Virgin Islands

4.83 out of 5 average rating, 29 reviews

Seaside Serenity apt

Relax at this unique and tranquil getaway. This location is perfect for anyone wanting the local experience. Walking distance from where the local fisherman comes in with the fresh catch of the day (lobster included.) It's also near some of the best restaurants on the island!!! (Ask me about D'Coal Pot Restaurant.) Immerse yourself in the local seaside swimming pool or ride the waves when the surf's up. Enjoy every little thing our beautiful piece of paradise has to offer!!!

1 – 8 Oct

$1,888 AUD total

Guest favourite

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

3 – 10 Aug

$6,704 AUD total

Guest favourite

Guesthouse in Tortola, British Virgin Islands

4.96 out of 5 average rating, 46 reviews

The Anchorage- Studio apt above Cane Garden Bay

We are back with a newly renovated guest room! Charming studio apartment on lower level of provencal estate, centrally located in the hills above Cane Garden Bay w/view of Jost Van Dyke & surf at Cane Garden Bay. Private terrace w/outdoor dining. Includes use of shared pool. Small trail through 1 acre of undeveloped but landscaped jungle. 4WD vehicle required. Property is 10 min drive to Road Town & Cane Garden Bay, 5 min to Nanny Cay. 30 min to airport & west end.

1 – 8 Dec

$2,221 AUD total

Guest favourite

Condo in East End, U.S. Virgin Islands

4.97 out of 5 average rating, 108 reviews

Beautiful corner unit condo right on the beach!

Location, location, location! Beautiful 2nd floor studio condo at Sapphire Resort & Marina in building A. This corner unit features a wrap around balcony ideal for enjoying the wonderful view of the sandy beach and turquoise waters. Unit features a king bed as well as a sleeper sofa. Kitchen is appointed with full oven/stove, dishwasher, microwave and refrigerator/freezer with ice maker. Come and enjoy all that St. Thomas has to offer!

24 – 31 Oct

$3,240 AUD total

Superhost

Villa in Tortola, British Virgin Islands

5.0 out of 5 average rating, 4 reviews

Villa Soleil, 3 BDs, Pool, January Discounted Rate

Villa Soleil is a luxuriously appointed vacation villa on the North shore of Tortola, British Virgin Islands. Privately nestled in the tropical hillside overlooking the paradisiacal Trunk Bay beach, this villa emanates the perfect balance of sophistication, style and comfort. There are 3 bedrooms, 2.5 bathrooms and 2 outdoor stone showers. Choose from, a King, Queen or Double/Twin bunk with King room (ideal for kids/family/couple)

9 – 16 Oct

$10,060 AUD total

Guest favourite

Apartment in Cruz Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 101 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.

2 – 9 Dec

$6,087 AUD total

Guest favourite

Villa in Brewers Bay, British Virgin Islands

4.84 out of 5 average rating, 43 reviews

Villa Matija

Villa Matija is nestled comfortably into the hillside overlooking Brewers Bay on Tortola in the British Virgin Islands. Allow yourself a little luxury and be eco-friendly at the same time! Villa Matija (pronounced ma-TEE-ya) sits above Brewers Bay with an outstanding view of Jost Van Dyke and several other smaller cays & islands. On a clear day you can see Puerto Rico (about 70 miles away)!

3 – 10 June

$5,361 AUD total

Guest favourite

Home in Roadtown, British Virgin Islands

4.95 out of 5 average rating, 87 reviews

Kerensa Villa

Stylish, secluded villa with pool and stunning views. Kerensa is close to gorgeous beaches and has panoramic views of the North coast and surrounding islands. You’ll love it because of the beautiful natural setting, the seclusion, the high end equipment and the quirky antiques and decor. It is ideal for romantic couples but can sleep up to 4 with a pull-out sofa-bed if required.

19 – 26 Dec

$8,348 AUD total

Superhost

Villa in Trunk Bay, British Virgin Islands

5.0 out of 5 average rating, 4 reviews

Ventana - modern villa, closest property to beach

Ventana - where every window frames a stunning view of an azure ocean and the rugged coastline of Trunk Bay enveloping the soft sandy beach below. Share quality time in this stylish minimalist villa, where every room and space hi-lights the stunning beach just yards below. Lounge by the pool or wander down the gravel track below that leads to this beautiful beach.

26 Sept – 3 Oct

$9,626 AUD total

Guest favourite

Condo in Road Town, British Virgin Islands

4.92 out of 5 average rating, 24 reviews

Modern condo with shared pool in Road Town-1 Room

Newly renovated 3 bedroom, 2 bathroom seaside condo located in Tobacco Wharf, Road Town; the capital of the British Virgin Islands. This property is located inside a lovely fenced yard with private parking, and beautiful gardens. It is in walking distance to the business center of town, shops, grocery stores, restaurants, banks, Tortola Sports Club etc.

30 Sept – 7 Oct

$2,140 AUD total