Fitness-friendly holiday rentals in Anguilla

1 Bedroom Luxury Condo Seconds to Beach + Terrace & Hot Tub

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.

Panarea Pool-Gym Villa, West End

Private wellness villa, 10-min walk to Maundays Bay, Belmond Cap Jaluca & Four Seasons. Rare West End privacy on gated ½-acre grounds with lush tropical gardens, sea-view infinity pool, wildlife, and exclusive gym. White-washed airy great room blends Caribbean-European charm; shaded lounge, BBQ deck, AC throughout. Minutes drive from Meads Bay and Anguilla’s best dining: Blanchards, Straw Hat, Jacala. Ideal escape for couples, families, wellness travelers, and foodies. Beach gear provided!

Cliffside Villa w/Pool Ideal for Family or Couples

Caribbean indoor-outdoor living at its very best! Enjoy spectacular sunsets and ocean views from the infinity pool at Spyglass Hill Villa. This gorgeous 4-bedroom villa is modern chic with an open, relaxed setting complete with many outdoor dining and lounging spaces. Enjoy the tropics with outdoor showers in the two master suites and an open-air courtyard inside. Fully equipped, this villa is perfect for a couple, family or group of friends. https://goo.gl/maps/Hg1wPqgXbj5jY8s89

Driftwood Haven | Bright & Breezy Studio Escape

Relax in this spacious first-floor unit in the Ankle House building at Driftwood Haven, West End, Anguilla—ideal for couples or solo travelers. It features a full kitchen, comfortable bed, private bathroom, and A/C for a restful stay. Guests enjoy access to a shared spa-pool, small gym, and free parking. Just a 3-minute drive to Maundays, Meads, and Rendezvous Bays, plus top resorts like Four Seasons, Cap Juluca, and Aurora. The perfect base for your Anguilla getaway!

Driftwood Haven | 2-Bedroom Villa w/ Private Pool

Enjoy this spacious 2-bedroom, 2.5-bathroom villa in Anguilla’s popular West End. Just a 3-minute drive to Maundays, Meads, and Rendezvous Bays, the villa features an open-plan living and kitchen area that opens to a private deck and small pool—perfect for relaxing or entertaining. Upstairs, both bedrooms offer en-suite bathrooms and private patios. Ideal for families or couples seeking comfort, style, and close proximity to the island’s best beaches and resorts.

Driftwood Haven | Chic Studio in West End

Discover comfort at this bright first-floor unit in the Ankle House building at Driftwood Haven, West End, Anguilla. Perfect for solo travellers or couples, it features a comfy bed, private bathroom, A/C, and a convenient kitchenette. Enjoy access to a shared spa-pool, small gym, and free parking. Just a 3-minute drive to Maundays, Meads, and Rendezvous Bays, plus top resorts like Cap Juluca and Four Seasons. A relaxing island escape in the heart of it all!

Fortune Rise. (Car rental available)

Fortune Rise is a licensed property that's falls under the villa business regulations Act. It's a newly built modern cozy apartment with remote gate access, back up generator and perimeter security camera system located in Mount Fortune on the eastern end of the island. Five minutes driving access to grocery stores, Island Harbour beach and the restaurants thereon like Falcon Nest. 10 minutes drive from the famous Shoal Bay beach.

Oceanfront Studio Villa w/Kitchen By Shoal Bay #10

Enjoy the seaside panoramic Caribbean views. Enjoy your oversized comfy king bed with kitchen, private terrace, fiber-optic internet, Smart TV, AC, club bar area, and complimentary paddle boards and kayaks. Scilly Cay is a 5 minute paddle away. Explore nearby beach bars and restaurants, with world famous Shoal Bay beach just 10 minutes away. On demand house keeping included if needed. We know you’ll love your stay.

Spacious Island Retreat with Backyard Fire Pit

Slow down, sink in, and savor island life just 10 minutes from Anguilla’s pristine beaches. • Cloud-soft queen bed with crisp hotel linens • Fresh pastries on your first morning • Roast marshmallows under the stars • AC and high-speed Wi-Fi • Private patio with fire pit & breezes • Concierge: massages, dinner, and more Smart TV, in-unit washer/dryer; just arrive. We’ll handle the rest.

Fortune Estate (Car rental available)

Newly built modern cozy apartment with remote gate access, back up generator and perimeter security camera system located in Mount Fortune on the eastern end of the island. Five minutes driving access to grocery stores, Island Harbour beach and the restaurants thereon like Falcon Nest. 10 minutes drive from the famous Shoal Bay beach.

Oceanfront 2BD Villa - Arawak Beach Club #6&7

Start your getaway at Arawak Beach Club's 2BR villa with Caribbean vistas. Private entrance, 2 terraces, beach steps away. Dining 5 min, Shoal Bay 10 min. Fiber Internet, Smart TV, AC bedrooms. Ocean breezes, 2 oceanfront patios, DIY bar. Paddleboards, kayaks. Optional rental car.

Oceanfront Suite w/Pool - Arawak Beach Club #8

Begin your journey at Arawak Beach Club's Suite #8 with Caribbean panoramas. Private terrace, beach bars steps away. Dining 5 min, Fiber Internet, Smart TV. Ocean breeze, AC. Communal seating, oceanfront patio. Paddle boards, kayaks included. Optional rental car.