Lesser Antilles Beach Vacations
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Top Beach vacation packages in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
La Playa Orient Bay
$622
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
9.4/10 Exceptional! (768 reviews)
The overall property was nice. There was mold on the ceiling from water leaking in the unit above. The shower leaks a lot of water onto the floor and the toilet rocks and needs tightened to the floor. The light above the kitchen sink only stays on a few seconds. The room was clean and overall resort was nice.
Reviewed on Aug 6, 2026
The Villas at Simpson Bay Resort
Pelican Key
$860
per person
Sep 9 - Sep 12
found 14 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Well day two of our stay it looked like it was raining in our room the air conditioner pipe broke water all over our kitchen when I went to the hotel front desk Mr.Walters never once apologized for the issue said we could move to sixth floor then back once it was fixed I refused to move twice, day four the toilet wouldn’t flush called front desk left for 5 hours came back still wasn’t fixed called again noone ever came my husband ended up fixing !!!Asked for a late check out for all the inconviences we dealt with was told if we pay for another day ,Would never stay here again ! Do better Simpson Villas
Reviewed on Aug 9, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
$790
per person
Sep 9 - Sep 12
found 14 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Great stay. Two weeks in unit m410. Beautiful views, spacious room, great staff. All the comforts of home. Only issues were a few days of rowdy guests. Large group of rude guests. Loud, drunk and obnoxious. They smoked cigars in the pool. Once this was brought to the attention of staff, it was handled. I’d stay here again.
Reviewed on Aug 10, 2026
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View all trips5* Beach vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, St. Thomas
$1,309
per person
Oct 10 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to St. Thomas (STT)
8.4/10 Very Good! (486 reviews)
Really enjoyed our stay. The beach was clean, staff was friendly. Utilize the golf carts to get around the property or get your steps in!
The lady LINDSEY will pick you up on the beach or other private charters.
Our goal was to roam the island and dine at different restaurants, we took advantage of all of the restaurants on property. The coffee shop was easy for a quick breakfast.
I would recommend bringing your own yeti or purchasing one in the coffee shop to prevent your drinks from melting so fast.
I loved hanging out under the tree.
And don’t forget to use the pool and beach near Coconut Cove restaurant/ resident side
Reviewed on Aug 9, 2026
Zemi Beach House, LXR Hotels & Resorts
$2,073
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to The Valley (AXA)
9.8/10 Exceptional! (279 reviews)
This place was amazing. Absolutely everything was amazing. Thank you Charisma for being awesome and making us feel welcomed from the first interaction. Thank you to the ladies at Zemi Thai Spa for a remarkable experience. The breakfast, food and drinks were chefs kiss. 10/10! No complaints, nothing but wonderful things to say ❤️
Reviewed on Aug 9, 2026
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View all trips3 Night Beach vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
$790
per person
Sep 9 - Sep 12
found 14 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Great stay. Two weeks in unit m410. Beautiful views, spacious room, great staff. All the comforts of home. Only issues were a few days of rowdy guests. Large group of rude guests. Loud, drunk and obnoxious. They smoked cigars in the pool. Once this was brought to the attention of staff, it was handled. I’d stay here again.
Reviewed on Aug 10, 2026
The Villas at Simpson Bay Resort
Pelican Key
$860
per person
Sep 9 - Sep 12
found 14 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Well day two of our stay it looked like it was raining in our room the air conditioner pipe broke water all over our kitchen when I went to the hotel front desk Mr.Walters never once apologized for the issue said we could move to sixth floor then back once it was fixed I refused to move twice, day four the toilet wouldn’t flush called front desk left for 5 hours came back still wasn’t fixed called again noone ever came my husband ended up fixing !!!Asked for a late check out for all the inconviences we dealt with was told if we pay for another day ,Would never stay here again ! Do better Simpson Villas
Reviewed on Aug 9, 2026
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See all available trips from Columbus to Lesser Antilles
View all trips4 Night Beach vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
$695
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Great stay. Two weeks in unit m410. Beautiful views, spacious room, great staff. All the comforts of home. Only issues were a few days of rowdy guests. Large group of rude guests. Loud, drunk and obnoxious. They smoked cigars in the pool. Once this was brought to the attention of staff, it was handled. I’d stay here again.
Reviewed on Aug 10, 2026
The Villas at Simpson Bay Resort
Pelican Key
$817
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Well day two of our stay it looked like it was raining in our room the air conditioner pipe broke water all over our kitchen when I went to the hotel front desk Mr.Walters never once apologized for the issue said we could move to sixth floor then back once it was fixed I refused to move twice, day four the toilet wouldn’t flush called front desk left for 5 hours came back still wasn’t fixed called again noone ever came my husband ended up fixing !!!Asked for a late check out for all the inconviences we dealt with was told if we pay for another day ,Would never stay here again ! Do better Simpson Villas
Reviewed on Aug 9, 2026
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See all available trips from Columbus to Lesser Antilles
View all tripsFind your perfect Lesser Antilles beach vacation
How do I book the best Lesser Antilles beach vacation packages?
Life’s a beach when you dive into our brilliant Lesser Antilles beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in Lesser Antilles?
A rental steps from the shore creates an amazingly affordable Lesser Antilles beach vacation. Seaside sojourns during low season start from $622. Prices and availability are subject to change. Additional terms may apply.
When should I book a Lesser Antilles beach holiday?
For a bustling beach break, book in . For a less crowded coast, is the time to turn up.
How can I book the best family beach vacations in Lesser Antilles?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a Lesser Antilles beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a Lesser Antilles vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find Lesser Antilles beach vacation deals?
Sort your search results by deals to delight in amazing Lesser Antilles beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a Lesser Antilles beach trip with free cancellation and/or flexible dates?
Just like the Lesser Antilles tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my Lesser Antilles beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Lesser Antilles. (OK, maybe not that last part.)
Top Beach Lesser Antilles Hotels
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
- 4 hours drive from Oyster Bay Marina
This hotel is a few steps from Pineapple Beach, where you can watch the sunset on your beach trip. Amenities at Margaritaville Vacation Club - St. Thomas include ...
8/10 Very Good! (2,507 reviews)
"Staff was very helpful. Big negative:no housekeeping services"
Reviewed on Aug 10, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
- 12 min drive from Oyster Bay Marina
At this spa all-inclusive property, get ready to stroll along the shore in Lowlands, as you'll be a short walk from Maho Beach. Amenities at Sonesta Maho Beach ...
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
- 4 hours drive from Oyster Bay Marina
Recharge at this luxury spa resort and get ready to watch the sunset on the beach in St. Thomas, as you'll be not far from Morningstar Beach. Amenities at The ...
8.4/10 Very Good! (1,378 reviews)
Travelers like: close to beach, cabanas, beach bars, beach towels
Travelers say...
"The staff was friendly and the grounds were beautiful!"
Reviewed on Aug 10, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
