Top Caribbean Places to Stay & Vacation Rentals with Long term stays allowed

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Island in Provincia de Cartagena, Colombia

4BR Stunning Island in Blue Sea with Pool KALUA★

12 beds

Mar 20 – 27

$2,246 per night

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Loft in Heredia, Costa Rica

Alianz Loft

2 beds

Jun 14 – 21

$244 per night

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Home in Sosua, Dominican Republic

Casa Cascada - Check out my other listing!

3 king beds

Dec 3 – 10

$249 per night

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Guest suite in San Juan, Puerto Rico

Treehouse w floating deck at La Botanica

1 queen bed

Dec 15 – 22

$190 per night

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Villa in Las Terrenas, Dominican Republic

Amazing sea view luxury modern, fully staffed

7 beds

Jun 14 – 21

$574 per night

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Home in North Side, Cayman Islands

Ocean's Edge: Beachfront Home with Rooftop Views

6 beds

Nov 25 – Dec 2

$704 per night

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Home in Fort Lauderdale, Florida

★Near Downtown & Beach- Luxury House /Heated spa★

8 beds

Dec 6 – 13

$800 per night

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Home in Stake Bay, Cayman Islands

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

3 beds

Mar 29 – Apr 5

$390 per night

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Home in Placida, Florida

Camp GoodNow: Stunning new beachfront home, private balcony off master!

4 beds

Sep 25 – Oct 2

$448 per night

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Superhost

Cottage in Eleuthera Island Shores, Bahamas

SHOREBREAK ECO COTTAGE

2 queen beds

May 27 – Jun 3

$395 per night

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Boat in Miami Beach, , Florida

Jewel of the Nile Yacht Hotel and Cruises

5 beds

Jul 14 – 21

$1,045 per night

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Superhost

Hotel room in Rincon, Puerto Rico

Tres Sirenas Boutique Hotel Oceanfront Suite

1 queen bed

Aug 16 – 23

$468 per night

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Home in Grand Cayman, Cayman Islands

We'll Sea

2 queen beds

Feb 6 – 13

$756 per night

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Villa in Kralendijk, Bonaire, Sint Eustatius and Saba

Villa Shores 32; Private Stunning Oceanfront Villa

5 beds

May 8 – 15

$1,188 per night

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Apartment in Isabela, Puerto Rico

Villa Shacks 2 bedroom-Unit 1

3 beds

Apr 25 – May 2

$285 per night

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Superhost

Home in San Cayetano de Venecia, Costa Rica

Quinta La Ceiba Modern Home with Pool in DairyFarm

3 beds

May 4 – 11

$175 per night

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Superhost

Condo in Montego Bay, Jamaica

Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.

2 beds

Apr 11 – 18

$181 per night

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Apartment in Montego Bay, Jamaica

Oceanfront Apt w/ Beach Access, Pool, & Gym (2F)

1 king bed

Dec 15 – 22

$257 per night

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Hut in Bavaro, Dominican Republic

Rekindle a Romance in a Retro Thatched Hut on the Beach

1 king bed

Oct 8 – 15

$175 per night

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Cabin in Bluefields, Jamaica

Cozy Oceanview Cabin

1 bed

Jan 4 – 11

$92 per night

951 stays