Lesser Antilles Holiday Rentals, Caribbean: Private House Rentals

A beach with yellow lounge chairs, palm trees, a boat, and a pier.

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Go beyond your typical stay in Lesser Antilles

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Condo

Villa

Spa

Hot tub

Resort

Family friendly

Cottage

Waterpark

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Our top choices for Lesser Antilles hotels

On the beach, white sand, sun-loungers, beach umbrellas

Townhome, 3 Bedrooms | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

1. Nanny Cay Resort and Marina

Road Town

Melissa

฿6,846

฿8,215 total

includes taxes & fees

10 Sept - 11 Sept

6 outdoor pools, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

4 restaurants; breakfast, lunch and dinner served

2. Simpson Bay Resort, Marina & Spa

Pelican Key

indhira

฿5,219

฿6,263 total

includes taxes & fees

13 Sept - 14 Sept

Deluxe Oceanfront Suite | Minibar, in-room safe, laptop workspace, blackout curtains

3. The Morgan Resort Spa Village

Simpson Bay

Juan Carlos

฿14,586

฿17,816 total

includes taxes & fees

10 Sept - 11 Sept

5 restaurants; breakfast, lunch and dinner served

On the beach, sun-loungers, beach umbrellas, beach towels

4. Sonesta Maho Beach All Inclusive Resort Casino & Spa

Lowlands

Steven

฿11,222

฿13,579 total

includes taxes & fees

5 Oct - 6 Oct

3 outdoor pools, pool umbrellas, pool loungers

Villa, 4 Bedrooms | Living area | 42-inch plasma TV with satellite channels, TV, pay films

5. Scrub Island Resort, Spa & Marina

Scrub Island

Joseph

฿14,114

฿18,911 total

includes taxes & fees

9 Oct - 10 Oct

Deluxe Penthouse, Balcony, Ocean View (Cool Water 1) | View from room

Deluxe Penthouse, Balcony, Ocean View (Cool Water 1) | Living area | 55-inch Smart TV with satellite channels, TV

6. Cane Garden Bay Beach Hotel

Cane Garden Bay

Joseph

฿9,177

฿11,471 total

includes taxes & fees

10 Sept - 11 Sept

Outdoor pool, pool umbrellas, pool loungers

Premier Studio, 1 King Bed, Ocean View | Private kitchen | Coffee/tea maker, mini-fridge, stovetop, toaster

7. Old Crow Hotel and Suites

Vieques

Alexis

฿3,256

฿3,727 total

includes taxes & fees

10 Sept - 11 Sept

Single Room | Desk, laptop workspace, blackout curtains, iron/ironing board

Double Room | Living area | 32-inch flat-screen TV with cable channels, TV

8. The Paradise Inn

Philipsburg

Carlisle

฿3,404

฿3,575 total

includes taxes & fees

10 Sept - 11 Sept

2 outdoor pools, pool umbrellas, pool loungers

9. Hommage Hotel & Residences

Nettle Bay

Anneka T

฿6,049

฿6,291 total

includes taxes & fees

11 Sept - 12 Sept

Deluxe Triple Room | In-room safe, desk, free WiFi

10. The Moorings Yacht Club Hotel

Road Town

Paul

฿6,362

฿7,635 total

includes taxes & fees

10 Sept - 11 Sept

Room, 2 Queen Beds, Beachfront | Premium bedding, in-room safe, iron/ironing board, free WiFi

Studio, 1 King Bed, Beachside | Premium bedding, in-room safe, iron/ironing board, free WiFi

Deluxe Studio, 1 King Bed, Beachside | Property grounds

11. Mary's Boon Beach Resort & Spa

Simpson Bay

Christopher

฿4,112

฿4,934 total

includes taxes & fees

10 Sept - 11 Sept

Deluxe Suite, 1 King Bed | View from room

12. Sea Gate Hotel

Isabel II

Jose

฿2,590

฿3,038 total

includes taxes & fees

10 Sept - 11 Sept

Superior Condo, 2 Bedrooms, Garden View | Private kitchen | Coffee/tea maker, mini-fridge

Superior Condo, 2 Bedrooms, Garden View | Living area | Flat-screen TV

13. Village Cay Hotel and Marina

Wickhams Cay 1

Andrea

฿5,329

฿6,288 total

includes taxes & fees

10 Sept - 11 Sept

14. The Villas at Simpson Bay Resort

Pelican Key

melissa

฿5,907

฿7,089 total

includes taxes & fees

13 Sept - 14 Sept

Penthouse, 2 Bedrooms, 2 Bathrooms, Ocean View | View from room

15. Royal Islander Resort La Plage

Lowlands

Amani

฿5,827

฿7,051 total

includes taxes & fees

30 Sept - 1 Oct

Outdoor pool, pool cabanas (surcharge), pool umbrellas

16. JW Marriott St. Maarten Beach Resort & Spa

Oyster Pond

Marcus ReShaun

฿11,808

฿15,224 total

includes taxes & fees

10 Sept - 11 Sept

Signature Tree House, 1 Queen Bed, Kitchen, Garden View | Terrace/patio

Luxury Tree House, 1 Queen Bed, Kitchen, Ocean View | Premium bedding, down duvets, in-room safe, laptop workspace

Superior Cabin, 1 King Bed, Kitchen, Garden View | Premium bedding, down duvets, in-room safe, laptop workspace

17. Finca Victoria

Vieques

Alysha

฿6,606

฿7,200 total

includes taxes & fees

12 Sept - 13 Sept

Premium bedding, down duvets, free WiFi, bed sheets

18. Fantastic Hotel

Marigot

Daniel

฿3,269

฿3,400 total

includes taxes & fees

12 Sept - 13 Sept

40-inch flat-screen TV with satellite channels, TV

Lighthouse 3 Bedroom Condo with Private Pool 1A | Terrace/patio

19. Oyster Bay Beach Resort

Oyster Pond

Eve

฿5,789

฿6,947 total

includes taxes & fees

10 Sept - 11 Sept

Deluxe Duplex | Living area | 32-inch Smart TV with cable channels, TV, Netflix

20. Edwards Guesthouse

Sandy Ground

Maricela

฿4,010

฿5,211 total

includes taxes & fees

10 Oct - 11 Oct

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Holiday Rentals in Lesser Antilles

Aparthotel

Deluxe Apartment, 3 Bedrooms, Balcony, Beach View | Living area | Smart TV

Deluxe Condo, 1 Bedroom, Beach View | Living area | Smart TV

Deluxe Apartment, 3 Bedrooms, Balcony, Beach View | Premium bedding, in-room safe, laptop workspace, soundproofing

Fourteen at Mullet Bay

Maho

"Delightful stay and walking distance of AUC medical school which was a plus."

Aparthotel

Superior Apartment, Balcony, Ocean View | Private kitchen | Espresso maker, coffee/tea maker, full-sized fridge, microwave

Panorama Residences at Monte Vista

Point Blanche

"Beautiful place would definitely recommend"

Cottage

Deluxe Cottage, Kitchen, Garden View (Calypso) | In-room safe, iron/ironing board, free cots/infant beds, free WiFi

Cottages by the Sea

Frederiksted

"I really enjoyed my stay at the Cottages. The beds were very comfortable and rooms were clean. The shower was very room. The my room didn't have an ocean view but ocean view was only a few short steps away. The people were very friendly and hospitable. I definitely recommend!"

Aparthotel

Studio with Balcony | Free WiFi, bed sheets

Bluebeard's Castle Resort

Charlotte Amalie

"Beautiful property our family loved our stay here"

Aparthotel

Beautiful 2 Bedroom - 2 Bathroom | Living area | Smart TV

The Hills Residence

Simpson Bay

"Very good"

Aparthotel

Luxury Villa, 1 King Bed with Sofa bed | Beach/ocean view

Dickenson Bay Oasis Antigua Village

Dickenson Bay

"Great location friendly staff beautiful grounds"

Apartment

Soundproofing, iron/ironing board, free WiFi, individually decorated

The Lighthouse Villas

Cane Garden Bay

"It was a perfect location and a charming hotel. Friendly staff and a great view!"

Villa

Private beach, white sand, sun-loungers, beach towels

Fort Recovery Beachfront Resort

West End

"Enjoyed."

Villa

Coffee/tea maker, fridge, microwave, cookware/dishes/utensils

Ke Villas

West End

"Great place great service and really friendly staff"

Apartment

703: Grand Studio Suite, 1 Queen Bed, Sea View | Egyptian cotton sheets, premium bedding, Select Comfort beds

802:Grand Apartment, 1 bedroom, 1 living room | Living area | 55-inch Smart TV with satellite channels, Netflix, Hulu

801:Grand Apartment, 1 Queen Bed, Sea View | Living area | 55-inch Smart TV with satellite channels, Netflix, Hulu

Mullet Bay Suites: Your Luxury Stay Awaits

Maho

"This place was amazing. Perfect experience"

Villa

Superior Cottage, 2 Bedrooms, Air conditioning, Ocean View | Living area | 65-inch Smart TV with digital channels, Netflix, streaming services

65-inch Smart TV with digital channels, Netflix, streaming services

Villa Island Paradise

St. John

"Such an amazing place to stay at St. Johns. Very clean, comfortable and cool. Balcony was exceptional and they had snorkeling gear which was so cool! Will definitely return. This was our 2nd time at st . John's"

Aparthotel

Deluxe Double Room | Down duvets, free WiFi, bed sheets

Deluxe Triple Room | Down duvets, free WiFi, bed sheets

July Apartments

Madame's Estate

"The property was no frills and the staff super helpful. Would stay again!"

Apartment

South Point Antigua Ocean Suites

English Harbour

"Great location, big rooms"

Villa

White Bay Villas and Beach Club

Jost Van Dyke

"We loved White Bay Villas! Maria and Bruno were amazing and took great care of us. The villa was clean and just perfect like the view. Can't wait to come back!"

Aparthotel

2 Bedroom Ocean View 2 Kings Suite | Living area | TV, table football

Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

"Fantastic location. Great little beach right next to hotel"

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Stay near popular Lesser Antilles attractions

A beach with clear turquoise water, a large tree, and a distant hill with buildings.

Sapphire Beach

9.0/10 (1,479 reviews)

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

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A beach with clear turquoise waters, a large airplane flying overhead, and a row of hotels in the background.

Maho Beach

8.8/10 (2,865 reviews)

Nothing says holiday like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Visit the top-notch restaurants or lively bars in this romantic area.

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A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Trunk Bay

9.6/10 (1,107 reviews)

Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.

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A beach with white sand, turquoise water, and a green hill in the background.

Flamenco Beach

9.2/10 (225 reviews)

If a restful holiday is part of your travel plans, Flamenco Beach might be the perfect place to visit during your trip to Culebra. Stroll along the seaside or seek out the snorkelling spots.

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A sandy beach with clear turquoise water, a large tree, and a hill with greenery in the background.

Magens Bay Beach

9.4/10 (1,559 reviews)

Appreciate the excellent views of hilly forests as you meander along a scenic trail on your way to this haven of white sand and inviting water.

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Virgin Islands National Park

9.6/10 (899 reviews)

Hike on scenic trails, explore sugar plantation ruins and snorkel along an underwater trail in this pristine nature park, which covers much of St. John.

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A beach with blue lounge chairs and a palm tree.

Bolongo Bay

8.2/10 (352 reviews)

Commune with nature and explore the great outdoors at Bolongo Bay during your travels in St. Thomas. Wander the beautiful beaches in this relaxing area.

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A beach with two palm trees, a red umbrella, and two beach chairs.

Jolly Beach

9.0/10 (789 reviews)

Why not spend a care-free afternoon at Jolly Beach during your travels in Jolly Harbour? While in this relaxing area, you can savour the top-notch restaurants.

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Learn more about Lesser Antilles

Island views, seaside views and top sights from Maho Beach to Sapphire Beach—discover Lesser Antilles, a tropical destination also famous for its port.

See all hotels in Lesser Antilles

Top Lesser Antilles Hotel Reviews

Hawksbill Resort Antigua

8/10 Good

"Vintage type property which doesn’t take away from the elegance, however foul smells are present when walking to and from rooms, water pressure in bathroom is good and hot, soaps are good towels are ages and have been in use for a while. WiFi on the property is excellent, barely any dead zones. Food is ok, wide enough variety however the flies and birds can get annoying while enjoying your meal and it is open air seating so it gets hot. Shops aren’t very close but a taxi can get you to and from the town quickly. Not many activities on the resort and it’s more laid back and quiet if that’s what you like, I was fine with relaxing. Mini fridge was always stocked and included with stay. Not all rooms have a tv so plan accordingly. Beds are comfortable and the views are amassing, it is a hilly resort so a lot of ramps and stairs to get from the rooms to the front desk and to the buffet. Overall the property is good, it needs renovations in the restrooms available to the public, more water stations outside of the buffet would be good, I didn’t tour the entire property so not sure if there were, staff is very pleasant and accommodating. I would stay again with the knowledge I have now, also it rains every other hour it seems so have an umbrella handy, also an insulated water bottle would be helpful with plenty of sunscreen. Drinks from the bar are good, there’s enough wine to knock you out with every meal."

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent

"Chef Dexter was phenomenal and patient. He treated me like family. I will definitely stay again!"

Margaritaville Vacation Club - St. Thomas

10/10 Excellent

"Was a great experience? The shuttle service to the rooms made me feel very exclusive and luxurious, just have to note the times they do start and stop the service. Staff were all the way helpful. Everyone on the compound was glad to help. The surrounding areas where lovely. Pool, ocean view everything. With live music, food and drinks I had a blast!"

Simpson Bay Resort, Marina & Spa

8/10 Good

"Well maintained property, near airport, restaurants and nightlife. Room was nice and clean, staff very helpful & friendly"

Divi Little Bay Beach Resort

10/10 Excellent

"Amazing place! Small and great! My room was beautiful and I walked out right into the beach! It’s close enough to everything and far away enough so it’s quiet and peaceful! I went without my kids and that was fine. I would like to return with them but I didn’t see any water slides or playground or babysitting so I’m not sure how kid friendly it is."

Oyster Bay Beach Resort

10/10 Excellent

"Everything about this resort is amazing the staff is amazing the shuttle is great definitely not my last trip to this awesome resort thank guys"

The Westin St. Thomas Beach Resort & Spa

8/10 Good

"It was convenient and clean"

Royal Islander Resort La Plage

10/10 Excellent

"Check in was very easy! The views absolutely cannot be beat. We worried it may be a bit loud with night clubs nearby but we slept soundly! The pool is excellent and the restaurant on property absolutely SPOILED my daughter for her birthday dinner. Already planning on coming back!"

Bunker Hill Hotel

8/10 Good

"The outside of the building need some work to be done"

More cheap stays in Lesser Antilles

Adonis Cupecoy

Jordan Road Lowlands

฿2,475

฿2,599 total

15 Sept - 16 Sept

includes taxes & fees

Sea Gate Hotel

Route 989 Km .04 Vieques

฿2,590

฿3,038 total

10 Sept - 11 Sept

includes taxes & fees

9.6/10 Exceptional! (1,008 reviews)

Casa de Tortuga

6 Calle Hucar Vieques Vieques

฿3,289

฿3,585 total

17 Sept - 18 Sept

includes taxes & fees

Old Crow Hotel and Suites

Barrio Florida, Carr.201 km 1.3 Vieques Puerto Rico

฿3,256

฿3,727 total

10 Sept - 11 Sept

includes taxes & fees

Cocovaa

34 white sands rd Simpson Bay

฿4,039

฿4,847 total

14 Sept - 15 Sept

includes taxes & fees

8.6/10 Excellent! (109 reviews)

Mamacita's Guest House

Calle Castelar #64 Culebra

฿4,144

฿5,011 total

10 Sept - 11 Sept

includes taxes & fees

8.2/10 Very good! (637 reviews)

Find out more about Lesser Antilles

Best time to go to Lesser Antilles

The best time to visit Lesser Antilles depends on your weather preferences. The hottest average temperature around Lesser Antilles is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Lesser Antilles is in February and March. March is mostly sunny.

Calendar Month	Temperature	Precipitation	Cloudiness
January	78.3°F (25.7°C)	No Rain	Mostly Sunny
February	77.7°F (25.4°C)	No Rain	Mostly Sunny
March	77.7°F (25.4°C)	No Rain	Mostly Sunny
April	78.8°F (26.0°C)	No Rain	Mostly Sunny
May	80.4°F (26.9°C)	Light Rain	Mostly Sunny
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny
July	82.2°F (27.9°C)	Light Rain	Mostly Sunny
August	82.8°F (28.2°C)	Light Rain	Mostly Sunny
September	82.9°F (28.3°C)	Light Rain	Mostly Sunny
October	82.6°F (28.1°C)	Light Rain	Mostly Sunny
November	81.1°F (27.3°C)	Light Rain	Mostly Cloudy
December	79.5°F (26.4°C)	No Rain	Mostly Sunny

Find hotels in Lesser Antilles from ฿2,599

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Lesser Antilles

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Lesser Antilles hotels

1. Nanny Cay Resort and Marina

2. Simpson Bay Resort, Marina & Spa

3. The Morgan Resort Spa Village

4. Sonesta Maho Beach All Inclusive Resort Casino & Spa

5. Scrub Island Resort, Spa & Marina

6. Cane Garden Bay Beach Hotel

7. Old Crow Hotel and Suites

8. The Paradise Inn

9. Hommage Hotel & Residences

10. The Moorings Yacht Club Hotel

11. Mary's Boon Beach Resort & Spa

12. Sea Gate Hotel

13. Village Cay Hotel and Marina

14. The Villas at Simpson Bay Resort

15. Royal Islander Resort La Plage

16. JW Marriott St. Maarten Beach Resort & Spa

17. Finca Victoria

18. Fantastic Hotel

19. Oyster Bay Beach Resort

20. Edwards Guesthouse

Holiday Rentals in Lesser Antilles

Fourteen at Mullet Bay

Panorama Residences at Monte Vista

Cottages by the Sea

Bluebeard's Castle Resort

The Hills Residence

Dickenson Bay Oasis Antigua Village

The Lighthouse Villas

Fort Recovery Beachfront Resort

Ke Villas

Mullet Bay Suites: Your Luxury Stay Awaits

Villa Island Paradise

July Apartments

South Point Antigua Ocean Suites

White Bay Villas and Beach Club

Hilton Vacation Club Royal Palm St. Maarten

Stay near popular Lesser Antilles attractions

Sapphire Beach

Maho Beach

Trunk Bay

Flamenco Beach

Magens Bay Beach

Virgin Islands National Park

Bolongo Bay

Jolly Beach

Learn more about Lesser Antilles

Top Lesser Antilles Hotel Reviews

Hawksbill Resort Antigua

Hilton Vacation Club Flamingo Beach St. Maarten

Margaritaville Vacation Club - St. Thomas

Simpson Bay Resort, Marina & Spa

Divi Little Bay Beach Resort

Oyster Bay Beach Resort

The Westin St. Thomas Beach Resort & Spa

Royal Islander Resort La Plage

Bunker Hill Hotel

More cheap stays in Lesser Antilles

Adonis Cupecoy

Sea Gate Hotel

Casa de Tortuga

Old Crow Hotel and Suites

Cocovaa

Mamacita's Guest House

Find out more about Lesser Antilles

Best time to go to Lesser Antilles

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