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
Save 100% on your flight
Price was $1,845, price is now $1,051 per person
$1,051
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 $2,254, price is now $1,082 per person
$1,082
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,651, price is now $1,177 per person
$1,177
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Agua Azul by Island Properties Online

Agua Azul by Island Properties Online

3.5 out of 5
Price was $1,544, price is now $1,202 per person
$1,202
per person
Jul 25 - Aug 1
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
Oyster Pond
Save 100% on your flight
Price was $3,226, price is now $2,552 per person
$2,552
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Bougainvillea by Island Properties Online

Bougainvillea by Island Properties Online

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $3,463, price is now $2,742 per person
$2,742
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Alizee by Island Properties Online

Alizee by Island Properties Online

3.5 out of 5
Save 100% on your flight
Price was $2,976, price is now $2,457 per person
$2,457
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
The Cliff

The Cliff

3 out of 5
Maho
Price was $1,655, price is now $1,419 per person
$1,419
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,381, price is now $1,188 per person
$1,188
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Villa Amalia

Villa Amalia

5 out of 5
Price was $6,737, price is now $5,877 per person
$5,877
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

3-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $946, price is now $720 per person
$720
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 $1,482, price is now $761 per person
$761
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,480, price is now $859 per person
$859
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,318, price is now $1,049 per person
$1,049
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $977, price is now $782 per person
$782
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,151, price is now $922 per person
$922
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,081, price is now $870 per person
$870
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,100, price is now $888 per person
$888
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,070, price is now $865 per person
$865
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,114, price is now $925 per person
$925
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Price was $1,770, price is now $1,478 per person
$1,478
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Sea Palace

Sea Palace

3 out of 5
Price was $831, price is now $726 per person
$726
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)

4-night Caribbean Islands vacations

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

Hotel La Plantation

4 out of 5
Price was $1,196, price is now $934 per person
$934
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,845, price is now $1,051 per person
$1,051
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,426, price is now $969 per person
$969
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,314, price is now $992 per person
$992
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,565, price is now $1,184 per person
$1,184
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 $2,262, price is now $1,767 per person
$1,767
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,319, price is now $1,035 per person
$1,035
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,488, price is now $1,174 per person
$1,174
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip 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
Price was $1,935, price is now $1,532 per person
$1,532
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,186, price is now $942 per person
$942
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,287, price is now $1,028 per person
$1,028
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Philipsburg (SXM)
Tradewinds at Simpson Bay

Tradewinds at Simpson Bay

3.5 out of 5
Price was $1,281, price is now $1,048 per person
$1,048
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 $1,146, price is now $833 per person
$833
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $2,254, price is now $1,082 per person
$1,082
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,990, price is now $986 per person
$986
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,503, price is now $902 per person
$902
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,608, price is now $1,067 per person
$1,067
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,676, price is now $1,162 per person
$1,162
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,215, price is now $874 per person
$874
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,620, price is now $1,180 per person
$1,180
per person
Aug 1 - Aug 6
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 $1,327, price is now $974 per person
$974
per person
Jul 19 - Jul 24
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
Price was $1,369, price is now $1,007 per person
$1,007
per person
Jul 19 - Jul 24
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 $2,223, price is now $1,649 per person
$1,649
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,829, price is now $1,361 per person
$1,361
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $1,240, price is now $848 per person
$848
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $2,597, price is now $1,131 per person
$1,131
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,948, price is now $1,406 per person
$1,406
per person
Aug 1 - Aug 8
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,893, price is now $989 per person
$989
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Save 100% on your flight
Price was $1,490, price is now $951 per person
$951
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,047, price is now $1,307 per person
$1,307
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,473, price is now $949 per person
$949
per person
Jul 25 - Aug 1
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
Save 100% on your flight
Price was $1,646, price is now $1,066 per person
$1,066
per person
Jul 25 - Aug 1
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 $1,706, price is now $1,113 per person
$1,113
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,907, price is now $1,255 per person
$1,255
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $2,122, price is now $1,441 per person
$1,441
per person
Aug 1 - Aug 8
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,368, price is now $1,655 per person
$1,655
per person
Aug 1 - Aug 8
found 22 hours ago
Roundtrip non-stop 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
$405 nightly
The price is $443 total per night
$443 total
Jun 23 - Jun 24
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
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
$232 nightly
The price is $297 total per night
$297 total
Jul 7 - Jul 8
Total with taxes and fees
When you stay at Serenade Punta Cana Beach & Spa Resort - All Inclusive in Punta Cana, you'll be on the waterfront, within a 15-minute drive of Cabeza de Toro Beach and Downtown Punta Cana.
On private beach
Pool
TRS Turquesa Hotel - Adults Only - All Inclusive

TRS Turquesa Hotel - Adults Only - All Inclusive

5 out of 5
Av. Francia Punta Cana La Altagracia
129.16 mi from city center
$280 nightly
The price is $359 total per night
$359 total
Jun 30 - Jul 1
Total with taxes and fees
With a stay at TRS Turquesa Hotel - Adults Only - All Inclusive in Punta Cana, you'll be 0.3 mi (0.5 km) from Cortecito Beach and 10.2 mi (16.4 km) from Macao Beach.
On private beach
Pool
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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.