Best Vacation Homes in Anguilla
Villa
10.0(53 Reviews)
4 Bedrooms
3 Baths
10 Guests
5000 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
CA $1,815/Night
7 Nights - CA $12,704
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
View
Parking
Air Conditioner
CA $182/Night
7 Nights - CA $1,277
Resort
9.8(267 Reviews)
1 Bath
Spa- Pool
- Balcony/Terrace
Breakfast
CA $1,090/Night
7 Nights - CA $7,627
House
10.0(37 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $388/Night
7 Nights - CA $2,715
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
CA $250/Night
7 Nights - CA $1,748
Villa
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $379/Night
7 Nights - CA $2,652
Villa
10.0(16 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $3,653/Night
7 Nights - CA $25,569
Villa
10.0(5 Reviews)
4 Bedrooms
1 Bath
8 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $2,695/Night
7 Nights - CA $18,868
Anguilla Luxury Rentals
Villa
10 Bedrooms
12 Baths
20 Guests
9999.67 ft²
Private Beach- Oceanfront
- Hot Tub
Fireplace/Heating
CA $9,272/Night
7 Nights - CA $64,903
Villa
7 Bedrooms
7 Baths
14 Guests
10494.81 ft²
- Private Pool
- Pool
- Parking
- Air Conditioner
CA $8,340/Night
7 Nights - CA $58,381
House
14 Bedrooms
12 Baths
34 Guests
2481.08 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
CA $7,714/Night
7 Nights - CA $54,001
Villa
5 Bedrooms
9 Baths
12 Guests
11840.3 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $7,285/Night
7 Nights - CA $50,995
Hotel
9.9(33 Reviews)
22 Baths
1243.72 ft²
- Oceanfront
- Hot Tub
- Spa
- Ocean View
CA $6,637/Night
7 Nights - CA $46,458
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
1345.49 ft²
- Pool
- View
- Parking
- Air Conditioner
CA $4,033/Night
7 Nights - CA $28,228
Villa
9.8(28 Reviews)
4 Bedrooms
4 Baths
10 Guests
7000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $3,935/Night
7 Nights - CA $27,548
Resort
9.7(3 Reviews)
11 Baths
50 Guests
1592.16 ft²
- Private Beach
- Oceanfront
- Spa
- Pool
CA $2,930/Night
7 Nights - CA $20,512
Anguilla Pet Friendly Vacation Rentals
Villa
9.4(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $866/Night
7 Nights - CA $6,066
Apartment
9.7(4 Reviews)
1 Bedroom
1 Bath
3 Guests
258.33 ft²
- Balcony/Terrace
Pet Friendly- Parking
- Air Conditioner
CA $278/Night
7 Nights - CA $1,945
Apartment
10.0(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
CA $449/Night
7 Nights - CA $3,140
Villa
10.0(31 Reviews)
4 Bedrooms
4 Baths
8 Guests
3500 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
CA $612/Night
7 Nights - CA $4,284
House
9.5(21 Reviews)
1 Bedroom
1 Bath
3 Guests
290.63 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
CA $125/Night
7 Nights - CA $874
Villa
10.0(18 Reviews)
3 Bedrooms
3 Baths
6 Guests
4000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $1,024/Night
7 Nights - CA $7,171
Villa
10.0(15 Reviews)
2 Bedrooms
2 Baths
8 Guests
2000 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
CA $554/Night
7 Nights - CA $3,875
Villa
10.0(14 Reviews)
5 Bedrooms
5 Baths
12 Guests
5000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $1,864/Night
7 Nights - CA $13,048
Anguilla Large Vacation Homes
Villa
9.6(7 Reviews)
5 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $1,540/Night
7 Nights - CA $10,780
Villa
9.8(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
21.53 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $552/Night
7 Nights - CA $3,867
Villa
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Spa
- Fireplace/Heating
- Pool
CA $1,366/Night
7 Nights - CA $9,565
Villa
9.6(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
Kitchen- Parking
- Air Conditioner
Internet
CA $297/Night
7 Nights - CA $2,082
Apartment
9.2(127 Reviews)
7 Bedrooms
6 Baths
24 Guests
742.71 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
CA $142/Night
7 Nights - CA $992
Villa
3 Bedrooms
2 Baths
12 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
CA $649/Night
7 Nights - CA $4,545
Villa
10.0(68 Reviews)
2 Bedrooms
1 Bath
5 Guests
2500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $916/Night
7 Nights - CA $6,415
Villa
10.0(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
2168 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $963/Night
7 Nights - CA $6,741
Why Choose Rent By Owner for your Anguilla Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Anguilla
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you make the most of your stay, whether you're seeking lively events or tranquil beaches in the area.
Peak Season Highlights
December to April
This is the most popular time to visit, when the weather is ideal for enjoying the beaches and outdoor activities. It’s the perfect season for those seeking warm days and clear skies in the region.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 70°F (21°C)
June to August
During these months, the area attracts visitors looking to experience the vibrant summer atmosphere and lively events. Expect busy accommodations and lively social scenes throughout this period.
Average Temperature Daytime: close to 88°F (31°C) - Nighttime: roughly 78°F (26°C)
Off-Season Highlights
May and November
Should you prefer fewer crowds, visiting during these months offers a more tranquil experience with pleasant weather. It’s an ideal time for relaxation and exploring at your own pace.
Average Temperature Daytime: around 85°F (29°C) - Nighttime: approximately 75°F (24°C)
September to October
These months are considered quieter, with fewer visitors and lower rates. While the weather can be slightly more unpredictable, it remains warm enough for outdoor pursuits in the region.
Average Temperature Daytime: about 86°F (30°C) - Nighttime: near 76°F (24°C)
Weekly Weather Forecast for Anguilla
How to Book Your Anguilla Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Anguilla
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Private outdoor swimming pools for relaxing in the sun.
- Spacious decks and patios to enjoy al fresco dining or evening gatherings.
- Well-maintained gardens and lush landscaping to enhance your outdoor experience.
- Direct access to pristine beaches for swimming, sunbathing, or beach walks.
- Outdoor grilling stations or barbecue grills for delicious cookouts.
- Shade structures like umbrellas or gazebos to stay cool during the day.
- Terraces with scenic views of the surrounding island landscape.
Top Attractions Around Anguilla
What attractions are nearby?
When staying in this destination, you'll find a variety of activities nearby, from relaxing on pristine beaches to exploring vibrant local culture, ensuring your experience here is both enjoyable and memorable.
Family Activities
- Meads Bay Beach: Spend a relaxing day on the pristine sands and calm waters, perfect for family picnics and building sandcastles.
- The Anguilla Great House Museum: Discover local history and culture together through engaging exhibits that appeal to all ages.
- Scilly Cay: Enjoy a fun-filled excursion by boat to this nearby island, where kids can indulge in beach activities and the whole family can savor fresh seafood.
- Corito Bay: Experience safe swimming and snorkeling in the tranquil waters of this protected bay, ideal for family bonding in the region.
Adult Activities
- Sailing and Yachting: Explore the pristine waters surrounding the area by chartering a private yacht or joining a sailing tour to experience the region’s stunning coastline from the sea.
- Gourmet Dining Experiences: Indulge in world-class cuisine at exclusive restaurants here, where you can savor local flavors and international dishes with a picturesque view of the ocean.
- Golfing in Scenic Settings: Play a round on meticulously maintained courses that offer panoramic views of the region’s natural beauty, perfect for relaxing amid lush landscapes.
- Spa and Wellness Retreats: Treat yourself to luxurious spa treatments at upscale resorts, designed to provide relaxation and rejuvenation amidst the tranquil surroundings.
Other Places to Stay in Anguilla
Long Bay Village
Little Harbour
Blowing Point
George Hill
Shoal Bay
Sandy Hill
Island Harbour
East End Village
The Valley
West End Village
The Quarter
Rendezvous Bay
Anguilla Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Savor authentic flavors at nearby eateries to fully experience the region’s culinary scene during your stay.
- Plan outdoor activities early: Take advantage of the area's beautiful beaches and outdoor pursuits by scheduling them in the mornings or late afternoons for the best weather.
- Communicate with your rental host: Reach out ahead of time to ask for personalized tips and local insights that can enhance your visit to this destination.
- Respect local customs and environment: Embrace eco-friendly practices and cultural traditions to ensure a responsible and enriching experience here.
Transportation Options
- Car Rentals: Renting a car gives you the flexibility to explore all that this island destination has to offer at your own pace.
- Taxis: Taxis are readily available for convenient, door-to-door transportation around the region, ideal for short trips or when arriving from the airport.
- Public Transportation: Local buses operate within the area, offering an affordable way to travel between popular spots and your vacation rentals.
- Private Transfers: Private shuttle services provide seamless arrival and departure transfers, ensuring comfort and reliability during your stay here.
Local Customs Options
- Greeting Etiquette: When visiting locals, it is customary to greet with a warm "Good morning" or "Good afternoon," reflecting the island's friendly and welcoming spirit.
- Dress Code for Religious and Cultural Sites: Modest attire is appreciated when attending church services or cultural events, ensuring respectful participation in local traditions.
- Respect for Land and Environment: Maintaining cleanliness and refraining from littering are vital customs here, emphasizing the community’s commitment to preserving the region’s natural beauty.
- Celebrating Local Festivals: Participating in or observing traditional festivities offers insight into the area's vibrant culture, with an emphasis on embracing the lively music and dance traditions.
Frequently Asked Questions About Anguilla?
1. What are the top vacation rentals in Anguilla?
There are a lot of options in Anguilla. If you plan on staying in the Anguilla area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Anguilla:
- Panoramic view of Crocus Bay; spacious; private; heated pool
- BellamareVilla, Shoal Bay East, Pool.
- Honeymooners! Romantic Private Anguilla Villa w/Pool, Ocean Views, Beach Access
- Villa Tasha Luxury Seafront Villa in Anguilla on the Caribbean sea AMAZING!
- DragonFly Studio, a charming place dedicated to relaxation
- Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
- Lockrum Point Villa: Seaside Villa 3 Bed/3 Bath/Pool
- Very Private & Personal, Villa Hibernia, Ocean Front Pool & Sea Gazebo,
- Penthouse Mimosa Great Views, Oceanfront Estate
- Anguilla ~ Three Dolphins Villa ~ 2025 Renovation
2. How many vacation rentals have private pools in Anguilla?
There are 165 vacation rentals with private pools near Anguilla. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Anguilla are best for families?
If you are looking for a family-friendly vacation home in Anguilla, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Anguilla:
4. How many Rentbyowner vacation rentals are available in Anguilla?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 546 in the Anguilla area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Anguilla.
5. What is the cancellation policy for vacation rentals in Anguilla?
Cancellation policies vary by listing, so it's important to review the specific terms provided on the property’s page. You can also contact the owner directly for detailed information regarding refunds and any applicable fees.
6. How do I ensure my booking in Anguilla is secure?
Bookings are secured through trusted payment methods outlined on the listing. Confirm that you use the official booking platform and communicate through verified channels to protect your transaction.
7. Are there any additional fees or charges when booking a vacation rental in this destination?
Additional fees such as cleaning fees, security deposits, or taxes may apply depending on the property. Details and exact amounts are listed on each rental’s description, but contacting the owner can provide clarity.
8. What amenities should I expect when staying in a vacation rental here?
Amenities vary between properties, ranging from WiFi to fully equipped kitchens and private pools. The specifics are detailed in the listing, and you can inquire directly with the owner for any special requests.
9. Is it possible to modify or extend my reservation in the region once booked?
Modifications depend on the individual property’s policies. You should reach out directly to the owner as soon as possible to discuss extending or altering your stay, and confirm if your plans can be accommodated.
Anguilla Top Rated Vacation Rentals
Apartment
10.0(1 Review)
1 Bedroom
2 Baths
5 Guests
1076.39 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $351/Night
7 Nights - CA $2,455
Hotel
9.6(52 Reviews)
18 Baths
2914.03 ft²
- Oceanfront
- Spa
- Pool
- Ocean View
CA $1,634/Night
7 Nights - CA $11,441
Resort
9.4(12 Reviews)
21 Baths
37 Guests
7330.23 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
CA $1,021/Night
7 Nights - CA $7,145
CA $487/Night
7 Nights - CA $3,408
Resort
9.2(65 Reviews)
29 Baths
68 Guests
1585.66 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
CA $699/Night
7 Nights - CA $4,891
CA $542/Night
7 Nights - CA $3,795
Apartment
9.0(71 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $267/Night
7 Nights - CA $1,872
House
9.0(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1496.18 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $377/Night
7 Nights - CA $2,639
