Cheap Vacations in Caribbean Islands

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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
Maho
Price was $784, price is now $553 per person
$553
per person
Apr 27 - May 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
Pelican Key
Price was $1,689, price is now $821 per person
$821
per person
Apr 27 - May 1
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
Pelican Key
Save 100% on your flight
Price was $1,984, price is now $1,148 per person
$1,148
per person
Apr 16 - Apr 20
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
Oyster Pond
Price was $1,250, price is now $725 per person
$725
per person
Apr 27 - May 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 $2,031, price is now $1,270 per person
$1,270
per person
Apr 20 - Apr 25
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 $1,373, price is now $926 per person
$926
per person
Apr 27 - May 1
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 $863, price is now $611 per person
$611
per person
Apr 27 - May 1
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 $772, price is now $555 per person
$555
per person
Apr 27 - May 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
Point Blanche
Price was $1,480, price is now $1,095 per person
$1,095
per person
Apr 27 - May 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 $1,113, price is now $858 per person
$858
per person
Apr 27 - May 1
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.
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 $704, price is now $559 per person
$559
per person
May 8 - May 11
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 $1,145, price is now $671 per person
$671
per person
May 8 - May 11
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 $1,202, price is now $785 per person
$785
per person
May 8 - May 11
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 $956, price is now $637 per person
$637
per person
May 8 - May 11
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 $1,250, price is now $881 per person
$881
per person
May 8 - May 11
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
Price was $1,109, price is now $798 per person
$798
per person
May 7 - May 10
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 $1,094, price is now $828 per person
$828
per person
May 8 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $755, price is now $576 per person
$576
per person
May 8 - May 11
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 $1,162, price is now $889 per person
$889
per person
May 8 - May 11
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 $780, price is now $600 per person
$600
per person
May 8 - May 11
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 $1,001, price is now $801 per person
$801
per person
May 8 - May 11
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 $977, price is now $782 per person
$782
per person
May 8 - May 11
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $784, price is now $553 per person
$553
per person
Apr 27 - May 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 $1,689, price is now $821 per person
$821
per person
Apr 27 - May 1
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 $1,984, price is now $1,148 per person
$1,148
per person
Apr 16 - Apr 20
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 $1,250, price is now $725 per person
$725
per person
Apr 27 - May 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 $1,373, price is now $926 per person
$926
per person
Apr 27 - May 1
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 $863, price is now $611 per person
$611
per person
Apr 27 - May 1
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 $772, price is now $555 per person
$555
per person
Apr 27 - May 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 $1,480, price is now $1,095 per person
$1,095
per person
Apr 27 - May 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 $1,193, price is now $899 per person
$899
per person
Apr 27 - May 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 $1,113, price is now $858 per person
$858
per person
Apr 27 - May 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 $1,792, price is now $1,402 per person
$1,402
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Port de Plaisance Resort, Trademark Collection by Wyndham

Port de Plaisance Resort, Trademark Collection by Wyndham

3.5 out of 5
Price was $1,013, price is now $840 per person
$840
per person
Apr 27 - May 1
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.
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Price was $1,200, price is now $969 per person
$969
per person
Apr 26 - May 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 $2,323, price is now $1,262 per person
$1,262
per person
Apr 17 - Apr 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
Price was $2,307, price is now $1,269 per person
$1,269
per person
Apr 17 - Apr 22
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 $2,031, price is now $1,270 per person
$1,270
per person
Apr 20 - Apr 25
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 $1,787, price is now $1,139 per person
$1,139
per person
Apr 17 - Apr 22
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 $1,628, price is now $1,177 per person
$1,177
per person
Apr 17 - Apr 22
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 $2,188, price is now $1,611 per person
$1,611
per person
Apr 17 - Apr 22
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 $1,851, price is now $1,483 per person
$1,483
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop 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
Price was $2,413, price is now $1,941 per person
$1,941
per person
Apr 20 - Apr 25
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 $1,616, price is now $1,304 per person
$1,304
per person
Apr 17 - Apr 22
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 $1,773, price is now $1,432 per person
$1,432
per person
Apr 17 - Apr 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
Price was $1,370, price is now $1,119 per person
$1,119
per person
Apr 28 - May 3
found 1 day 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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Save 100% on your flight
Price was $1,299, price is now $852 per person
$852
per person
May 1 - May 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
Save 100% on your flight
Price was $1,768, price is now $1,028 per person
$1,028
per person
May 1 - May 8
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 $1,437, price is now $876 per person
$876
per person
May 1 - May 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 $1,619, price is now $1,001 per person
$1,001
per person
May 5 - May 11
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 $2,383, price is now $1,483 per person
$1,483
per person
May 1 - May 8
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 $1,703, price is now $1,159 per person
$1,159
per person
May 1 - May 8
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 $2,569, price is now $1,877 per person
$1,877
per person
May 1 - May 8
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 $1,874, price is now $1,407 per person
$1,407
per person
May 1 - May 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 $2,468, price is now $1,875 per person
$1,875
per person
Apr 17 - Apr 23
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 $1,098, price is now $869 per person
$869
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,686, price is now $1,363 per person
$1,363
per person
May 1 - May 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was $1,966, price is now $1,607 per person
$1,607
per person
May 1 - May 8
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
The price is $525 total per night
$525 total
per night
Apr 12 - Apr 13
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.
Serenade Punta Cana Beach & Spa Resort - All Inclusive

Serenade Punta Cana Beach & Spa Resort - All Inclusive

4.5 out of 5
Carretera Cabeza de Toro Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
134.26 mi from city center
Get rates
With a stay at Serenade Punta Cana Beach & Spa Resort - All Inclusive in Punta Cana, you'll be within a 15-minute drive of Cabeza de Toro Beach and Downtown Punta Cana.
On private beach
Pool
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
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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.