Cheap Vacations in Caribbean Islands

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Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Vicky's Keys - Hostel

Vicky's Keys - Hostel

1.5 out of 5
Sucker Garden
Price was $581, price is now $477 per person
$477
per person
Jan 24 - Jan 31
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
Pelican Key
Save 100% on your flight
Price was $1,752, price is now $1,012 per person
$1,012
per person
Jan 22 - Jan 25
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
Downtown Philipsburg
Price was $1,293, price is now $973 per person
$973
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sea Palace

Sea Palace

3 out of 5
Downtown Philipsburg
Price was $1,178, price is now $958 per person
$958
per person
Jan 30 - Feb 5
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
Oyster Pond
Price was $845, price is now $688 per person
$688
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,217, price is now $1,870 per person
$1,870
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Artimino by Island Properties Online

Artimino by Island Properties Online

3.5 out of 5
Maho
Save 100% on your flight
Price was $2,251, price is now $1,901 per person
$1,901
per person
Feb 4 - Feb 11
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Cupecoy Beach Club

Cupecoy Beach Club

3 out of 5
Maho
Save 100% on your flight
Price was $1,796, price is now $1,532 per person
$1,532
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Belair
Price was $908, price is now $777 per person
$777
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Baker's Suites

Baker's Suites

3.5 out of 5
Price was $750, price is now $664 per person
$664
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop 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 $845, price is now $688 per person
$688
per person
Jan 19 - Jan 22
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 $2,164, price is now $1,221 per person
$1,221
per person
Feb 5 - Feb 8
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 $1,752, price is now $1,012 per person
$1,012
per person
Jan 22 - Jan 25
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 $1,640, price is now $1,073 per person
$1,073
per person
Feb 5 - Feb 8
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 $1,314, price is now $961 per person
$961
per person
Feb 5 - Feb 8
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 $1,240, price is now $909 per person
$909
per person
Feb 5 - Feb 8
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 $1,293, price is now $973 per person
$973
per person
Jan 19 - Jan 22
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 $1,578, price is now $1,210 per person
$1,210
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Price was $1,049, price is now $831 per person
$831
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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 $1,005, price is now $831 per person
$831
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Royal Islander Resort La Terrasse

Royal Islander Resort La Terrasse

4 out of 5
Price was $1,027, price is now $859 per person
$859
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,217, price is now $1,870 per person
$1,870
per person
Jan 19 - Jan 22
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.
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,209, price is now $957 per person
$957
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $2,021, price is now $1,015 per person
$1,015
per person
Jan 19 - Jan 23
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 $2,553, price is now $1,396 per person
$1,396
per person
Jan 31 - Feb 4
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 $1,648, price is now $1,102 per person
$1,102
per person
Jan 15 - Jan 19
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 $1,706, price is now $1,247 per person
$1,247
per person
Jan 15 - Jan 19
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 $2,255, price is now $1,650 per person
$1,650
per person
Jan 15 - Jan 19
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 $2,031, price is now $1,497 per person
$1,497
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip 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 $1,417, price is now $1,068 per person
$1,068
per person
Jan 31 - Feb 4
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 $1,271, price is now $1,000 per person
$1,000
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Price was $1,342, price is now $1,056 per person
$1,056
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
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 $1,770, price is now $1,433 per person
$1,433
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,786, price is now $2,323 per person
$2,323
per person
Jan 19 - Jan 23
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.
Adonis Cupecoy

Adonis Cupecoy

2.5 out of 5
Price was $603, price is now $460 per person
$460
per person
Jan 19 - Jan 24
found 20 hours 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 $2,444, price is now $1,041 per person
$1,041
per person
Jan 19 - Jan 24
found 20 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 $2,998, price is now $1,406 per person
$1,406
per person
Jan 19 - Jan 24
found 20 hours 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 $1,936, price is now $1,164 per person
$1,164
per person
Jan 19 - Jan 24
found 20 hours 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 $2,390, price is now $1,466 per person
$1,466
per person
Jan 19 - Jan 24
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,338, price is now $875 per person
$875
per person
Jan 19 - Jan 24
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Save 100% on your flight
Price was $1,426, price is now $953 per person
$953
per person
Jan 19 - Jan 24
found 20 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 $1,800, price is now $1,227 per person
$1,227
per person
Jan 19 - Jan 24
found 20 hours 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 $2,287, price is now $1,605 per person
$1,605
per person
Jan 19 - Jan 24
found 20 hours 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 $2,084, price is now $1,468 per person
$1,468
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Save 100% on your flight
Price was $1,667, price is now $1,209 per person
$1,209
per person
Jan 19 - Jan 24
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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 $1,109, price is now $897 per person
$897
per person
Jan 19 - Jan 24
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

6-7 night Caribbean Islands vacations

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

The Paradise Inn

3 out of 5
Price was $563, price is now $442 per person
$442
per person
Jan 24 - Jan 31
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 $3,369, price is now $1,409 per person
$1,409
per person
Jan 18 - Jan 25
found 19 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 $4,187, price is now $2,225 per person
$2,225
per person
Jan 24 - Jan 31
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 $1,987, price is now $1,119 per person
$1,119
per person
Jan 24 - Jan 31
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 $3,203, price is now $1,935 per person
$1,935
per person
Jan 24 - Jan 31
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
Save 100% on your flight
Price was $1,729, price is now $1,096 per person
$1,096
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Price was $2,097, price is now $1,367 per person
$1,367
per person
Jan 18 - Jan 25
found 19 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 $2,225, price is now $1,503 per person
$1,503
per person
Jan 24 - Jan 31
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 $3,059, price is now $2,133 per person
$2,133
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Adonis Cupecoy

Adonis Cupecoy

2.5 out of 5
Price was $734, price is now $524 per person
$524
per person
Jan 24 - Jan 31
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 $1,964, price is now $1,507 per person
$1,507
per person
Jan 30 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Save 100% on your flight
Price was $1,420, price is now $1,135 per person
$1,135
per person
Jan 24 - Jan 31
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
637 mi from city center
$471 nightly
The price is $516 total per night
$516 total
Jan 3 - Jan 4, 2026
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
Hotel Riu Republica - Adults only - All Inclusive

Hotel Riu Republica - Adults only - All Inclusive

4 out of 5
Playa Arena Gorda Punta Cana
126.6 mi from city center
Get rates
With a stay at Hotel Riu Republica - Adults only - All Inclusive in Punta Cana (Bávaro), you'll be within a 15-minute drive of Arena Gorda Beach and Cana Bay Golf Club.
Pool
Hot Tub
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
131.05 mi from city center
$404 nightly
The price is $518 total per night
$518 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
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.
Pool
Breakfast included
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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.