Title: Windward Islands Vacation Packages 2026 from $538 | Expedia.com

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![](https://images.trvl-media.com/place/553248635976409626/e2dde351-a30d-4d3a-8b41-8a16ce9b3f28.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windward Islands Vacations from $538

## Book a Hotel + Flight or Car together to unlock savings

## The Latest Windward Islands vacation packages

Price found within the past 48 hours. Click for updated prices.

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$538

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,874

per person

Apr 27 - May 2

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![SIRTAJ - Beverly Hills](https://images.trvl-media.com/lodging/7000000/6120000/6117200/6117111/868572f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SIRTAJ - Beverly Hills

South of Wilshire

$1,083

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Los Angeles (LAX)

8.4/10 Very Good! (1,001 reviews)

Excellent location, clean room, comfortable bed

Reviewed on Feb 15, 2026

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

$592

per person

Apr 27 - May 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

If you're looking for a super nice place to stay this is NOT that. It's an older hotel that serves It's purpose. Our room was very clean, AC was great, the bed & pillows are not comfortable but worked. The staff was extremely friendly. I would stay here again for a quick 2 night trip.

Reviewed on Feb 13, 2026

![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/06988314_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel Villa

South Beach

$564

per person

Apr 27 - May 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (997 reviews)

Room was clean only had a problem with the toilet it took them awhile to come fix it the breakfast was good and staff definitely did everything they could to make our stay comfortable even until check out they held our bags for us because we had a later flight from our check out.

Reviewed on Feb 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windward Islands

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-16/2026-03-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248635976409626)

### Discover the most popular places to visit in Windward Islands

![ellow and red lifeguard booth on Grand Anse Beach on Grenada Island](https://images.trvl-media.com/place/6073167/96524ea8-f64a-4e15-bade-e3a517ca2e7e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Grand Anse Beach

If a restful vacation is part of your travel plans, Grand Anse Beach might be the perfect place to seek out during your trip to Grand Anse. Make time to visit the area's shops, or simply enjoy its top-notch restaurants. 

[](https://expedia.com/Grand-Anse-Beach-Grenada.d6073167.Vacation-Attraction)

![Ponton du terminal croisières dans le centre ville de Fort-de-France.](https://images.trvl-media.com/place/553248635146436920/10fd2d82-e9f7-4566-ad08-a5bf649c2266.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cruise Terminal

Explore the waterfront in Fort-de-France with a trip to Cruise Terminal. While you're in the area, stroll along the beautiful beaches. 

[](https://expedia.com/Cruise-Terminal-Fort-de-France.d553248635146436920.Vacation-Attraction)

![Anse Chastanet Beach](https://images.trvl-media.com/place/6067561/b7099683-58ae-4932-bd36-7539b46bd0fb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Anse Chastanet Beach

Enjoy a pleasant Caribbean beach day surrounded by abundant natural beauty. Relax sunbathing on dark sand and snorkeling in crystal-clear waters.

[](https://expedia.com/Anse-Chastanet-Beach-Soufriere.d6067561.Vacation-Attraction)

## Windward Islands Hotel Deals

![Siesta Hotel](https://images.trvl-media.com/lodging/1000000/450000/443100/443089/1caf2548_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Siesta Hotel

Morne Rouge Street St. George's 

$111 nightly

$121 total

Feb 19 - Feb 20

Total with taxes and fees

8.8/10 Excellent! (1,014 reviews)

Everything was great.

Reviewed on Feb 10, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=443089&PinnedHotelID=443089&HadPinnedHotel=true&regionId=553248635976409626)

![Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort](https://images.trvl-media.com/lodging/16000000/15450000/15447000/15446956/5f1d48a1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Gros Islet Gros Islet 

Fully refundableReserve now, pay when you stay

$588 nightly

$588 total

Feb 17 - Feb 18

Total with taxes and fees

7.6/10 Good! (1,004 reviews)

The staff was great I felt very welcome.

Reviewed on Feb 12, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&selected=15446956&PinnedHotelID=15446956&HadPinnedHotel=true&regionId=553248635976409626)

![Radisson Grenada Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/16300/16281/99bd052a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Radisson Grenada Beach Resort

Grand Anse St. George's 

Fully refundableReserve now, pay when you stay

$250 nightly

$272 total

Mar 14 - Mar 15

Total with taxes and fees

8.2/10 Very Good! (1,560 reviews)

It was a great stay I really only have minor complaints. Let’s start with the good: Beautiful clean property. Excellent customer service by all of the staff. They are very kind and move with urgency and did everything to accommodate my requests. Beautiful property right on the beach with three lovely ...

Reviewed on Feb 13, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F14%2F2026&endDate=3%2F15%2F2026&selected=16281&PinnedHotelID=16281&HadPinnedHotel=true&regionId=553248635976409626)

[See all 6,667 properties in Windward Islands](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&regionId=553248635976409626)

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.

## Find the Best Windward Islands Vacation Packages

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