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 $1,394, price is now $768 per person
$768
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,097, price is now $1,152 per person
$1,152
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,919, price is now $1,099 per person
$1,099
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $4,300, price is now $2,815 per person
$2,815
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,778, price is now $1,242 per person
$1,242
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $2,298, price is now $1,643 per person
$1,643
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,769, price is now $1,265 per person
$1,265
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,232, price is now $890 per person
$890
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,034, price is now $1,470 per person
$1,470
per person
Dec 7 - Dec 12
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,217, price is now $1,610 per person
$1,610
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)

3-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $768, price is now $577 per person
$577
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,394, price is now $768 per person
$768
per person
Nov 27 - Nov 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,281, price is now $755 per person
$755
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,353, price is now $866 per person
$866
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $972, price is now $668 per person
$668
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,097, price is now $788 per person
$788
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,091, price is now $821 per person
$821
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,008, price is now $768 per person
$768
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $803, price is now $620 per person
$620
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was $2,686, price is now $2,169 per person
$2,169
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,095, price is now $892 per person
$892
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $758, price is now $624 per person
$624
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

4-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Price was $950, price is now $723 per person
$723
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,628, price is now $893 per person
$893
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,584, price is now $920 per person
$920
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,400, price is now $1,008 per person
$1,008
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,006, price is now $735 per person
$735
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,260, price is now $925 per person
$925
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,784, price is now $1,322 per person
$1,322
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,521, price is now $1,129 per person
$1,129
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,441, price is now $1,821 per person
$1,821
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,270, price is now $961 per person
$961
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $1,179, price is now $909 per person
$909
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,000, price is now $780 per person
$780
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

5-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,232, price is now $890 per person
$890
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,097, price is now $1,152 per person
$1,152
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,919, price is now $1,099 per person
$1,099
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $4,300, price is now $2,815 per person
$2,815
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,778, price is now $1,242 per person
$1,242
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Save 100% on your flight
Price was $2,298, price is now $1,643 per person
$1,643
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,769, price is now $1,265 per person
$1,265
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,034, price is now $1,470 per person
$1,470
per person
Dec 7 - Dec 12
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,217, price is now $1,610 per person
$1,610
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,762, price is now $1,338 per person
$1,338
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,546, price is now $1,184 per person
$1,184
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,281, price is now $988 per person
$988
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)

6-7 night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,069, price is now $725 per person
$725
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,199, price is now $1,054 per person
$1,054
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $2,341, price is now $1,158 per person
$1,158
per person
Nov 23 - Nov 30
just found
Roundtrip non-stop flight included
Boston (BOS) 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 $1,903, price is now $957 per person
$957
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,889, price is now $1,209 per person
$1,209
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $1,767, price is now $1,175 per person
$1,175
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $3,677, price is now $2,522 per person
$2,522
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,325, price is now $1,612 per person
$1,612
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,545, price is now $1,075 per person
$1,075
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Save 100% on your flight
Price was $1,181, price is now $853 per person
$853
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Save 100% on your flight
Price was $2,225, price is now $1,628 per person
$1,628
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Save 100% on your flight
Price was $1,208, price is now $886 per person
$886
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
$405 nightly
The price is $443 total per night
$443 total
Oct 25 - Oct 26
Total with taxes and fees
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
Wyndham Alltra Punta Cana All-Inclusive Resort

Wyndham Alltra Punta Cana All-Inclusive Resort

4 out of 5
Playas Uvero Alto Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
120.96 mi from city center
$271 nightly
The price is $271 total per night
$271 total
Oct 25 - Oct 26
Total with taxes and fees
Located in Punta Cana (Uvero Alto), Wyndham Alltra Punta Cana All-Inclusive Resort is within a 15-minute drive of Sirenis Aquagames Water Park and Macao Beach.
Pool
Breakfast included
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Mahoe Bay, Ironshore Montego Bay Saint James
489.91 mi from city center
Get rates
When you stay at Hotel Riu Montego Bay - Adults Only - All Inclusive in Montego Bay, you'll be on the beach, within a 15-minute drive of Rose Hall Great House and Doctor's Cave Beach.
Pool
Hot Tub
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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.