Cheap Vacations in Caribbean Islands

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Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,257, price is now $601 per person
$601
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,692, price is now $705 per person
$705
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,196, price is now $648 per person
$648
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,521, price is now $999 per person
$999
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $921, price is now $636 per person
$636
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,139, price is now $808 per person
$808
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Forest

The Forest

4 out of 5
Price was $1,340, price is now $963 per person
$963
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,075, price is now $776 per person
$776
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,709, price is now $1,240 per person
$1,240
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,521 per person
$1,521
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

3-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,149, price is now $632 per person
$632
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,492, price is now $724 per person
$724
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,090, price is now $774 per person
$774
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $994, price is now $763 per person
$763
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $903, price is now $736 per person
$736
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,578, price is now $1,287 per person
$1,287
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,116, price is now $921 per person
$921
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,107, price is now $915 per person
$915
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $947, price is now $794 per person
$794
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Price was $1,305, price is now $1,104 per person
$1,104
per person
Oct 16 - Oct 19
found 12 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,170, price is now $993 per person
$993
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Price was $1,690, price is now $1,440 per person
$1,440
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

4-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $746, price is now $574 per person
$574
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,692, price is now $705 per person
$705
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,257, price is now $601 per person
$601
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,196, price is now $648 per person
$648
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,313, price is now $888 per person
$888
per person
Oct 15 - Oct 19
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $921, price is now $636 per person
$636
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,139, price is now $808 per person
$808
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Forest

The Forest

4 out of 5
Price was $1,340, price is now $963 per person
$963
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,075, price is now $776 per person
$776
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,709, price is now $1,240 per person
$1,240
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,521 per person
$1,521
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $995, price is now $746 per person
$746
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

5-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,697, price is now $781 per person
$781
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,286, price is now $923 per person
$923
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,521, price is now $999 per person
$999
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $1,531, price is now $1,049 per person
$1,049
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,422, price is now $1,027 per person
$1,027
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Save 100% on your flight
Price was $2,575, price is now $1,861 per person
$1,861
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,283, price is now $928 per person
$928
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,070, price is now $787 per person
$787
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,275, price is now $958 per person
$958
per person
Oct 8 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Forest

The Forest

4 out of 5
Price was $1,657, price is now $1,251 per person
$1,251
per person
Oct 8 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,372, price is now $1,046 per person
$1,046
per person
Oct 8 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,292, price is now $994 per person
$994
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

6-7 night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,904, price is now $757 per person
$757
per person
Oct 3 - Oct 10
found 13 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,634, price is now $933 per person
$933
per person
Oct 3 - Oct 10
found 13 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,018, price is now $1,244 per person
$1,244
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Save 100% on your flight
Price was $1,610, price is now $1,025 per person
$1,025
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $1,935, price is now $1,264 per person
$1,264
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Bougainvillea by Island Properties Online

Bougainvillea by Island Properties Online

3.5 out of 5
Save 100% on your flight
Price was $3,321, price is now $2,663 per person
$2,663
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,628, price is now $1,312 per person
$1,312
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Cupecoy Beach Club

Cupecoy Beach Club

3 out of 5
Price was $2,170, price is now $1,756 per person
$1,756
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Paradiso by Island Properties Online

Paradiso by Island Properties Online

4 out of 5
Save 100% on your flight
Price was $4,063, price is now $3,386 per person
$3,386
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Price was $3,426, price is now $2,869 per person
$2,869
per person
Sep 23 - Sep 30
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Savana at Porto Cupecoy Marina

Savana at Porto Cupecoy Marina

3.5 out of 5
Price was $1,459, price is now $1,247 per person
$1,247
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
OASIS Apartments Simpson Bay

OASIS Apartments Simpson Bay

4 out of 5
Price was $1,344, price is now $1,160 per person
$1,160
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

Top rated hotels for your Caribbean Islands vacation

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard Nassau New Providence
Free Cancellation
Reserve now, pay when you stay
637 mi from city center
The price is $357 total per night
$357 total
per night
Sep 6 - Sep 7
When you stay at Grand Hyatt Baha Mar in Nassau, you'll be on the beach, within a 5-minute drive of Royal Blue Golf Club and Cable Beach.
Pool
Spa
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
200 Coco Beach Blvd. Highway 955-I Río Grande
Free Cancellation
Reserve now, pay when you stay
301.79 mi from city center
The price is $338 total per night
$338 total
per night
Sep 10 - Sep 11
Located in Río Grande (Zarzal), Hyatt Regency Grand Reserve Puerto Rico is within a 15-minute drive of Carabali Rainforest Park and The Outlet Ruta 66.
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

5 out of 5
Playas de Bavaro Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
131.05 mi from city center
The price is $382 total per night
$382 total
per night
Sep 22 - Sep 23
Located in Punta Cana (Bávaro), Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive is within a 15-minute drive of Downtown Punta Cana and Los Corales Beach.
Don't see what you're looking for?
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.