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Jamaica Vacation Rentals

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50 rentals in Jamaica.
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Peaceful Waterfront Getaway with Sandy Beach and Pier, vacation rental in Jamaica
Peaceful Waterfront Getaway with Sandy Beach and Pier, vacation rental in Jamaica
Peaceful Waterfront Getaway with Sandy Beach and Pier, vacation rental in Jamaica

Peaceful Waterfront Getaway with Sandy Beach and Pier

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Rappahannock River Unplugged

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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The Holidays in Irvington! A page out of Norman Rockwell!, vacation rental in Jamaica
The Holidays in Irvington! A page out of Norman Rockwell!, vacation rental in Jamaica
The Holidays in Irvington! A page out of Norman Rockwell!, vacation rental in Jamaica

The Holidays in Irvington! A page out of Norman Rockwell!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Guest house in peaceful, secluded setting, vacation rental in Jamaica
Guest house in peaceful, secluded setting, vacation rental in Jamaica
Guest house in peaceful, secluded setting, vacation rental in Jamaica

Guest house in peaceful, secluded setting

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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'Pop Castle' Historic Gem on the Rappahannock River, vacation rental in Jamaica
'Pop Castle' Historic Gem on the Rappahannock River, vacation rental in Jamaica
'Pop Castle' Historic Gem on the Rappahannock River, vacation rental in Jamaica

'Pop Castle' Historic Gem on the Rappahannock River

Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Private waterfront retreat on Mattaponi River near Williamsburg, vacation rental in Jamaica
Private waterfront retreat on Mattaponi River near Williamsburg, vacation rental in Jamaica
Private waterfront retreat on Mattaponi River near Williamsburg, vacation rental in Jamaica

Private waterfront retreat on Mattaponi River near Williamsburg

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
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Sunrise on Irvington's Carters Creek, vacation rental in Jamaica
Sunrise on Irvington's Carters Creek, vacation rental in Jamaica
Sunrise on Irvington's Carters Creek, vacation rental in Jamaica

Sunrise on Irvington's Carters Creek

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Guest Beach House on the York River, vacation rental in Jamaica
Guest Beach House on the York River, vacation rental in Jamaica
Guest Beach House on the York River, vacation rental in Jamaica

Guest Beach House on the York River

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Rappahannock River Retreat, vacation rental in Jamaica
Rappahannock River Retreat, vacation rental in Jamaica
Rappahannock River Retreat, vacation rental in Jamaica

Rappahannock River Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront, Pier, Breathtaking View,  Walk to Tides Inn&Irvington, vacation rental in Jamaica
Waterfront, Pier, Breathtaking View,  Walk to Tides Inn&Irvington, vacation rental in Jamaica
Waterfront, Pier, Breathtaking View,  Walk to Tides Inn&Irvington, vacation rental in Jamaica

Waterfront, Pier, Breathtaking View, Walk to Tides Inn&Irvington

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Jamaica
A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Jamaica
A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Jamaica

A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Relax on the Rappahannock, vacation rental in Jamaica
Relax on the Rappahannock, vacation rental in Jamaica
Relax on the Rappahannock, vacation rental in Jamaica

Relax on the Rappahannock

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lands End Lodge on the Rappahannock River - Where the Road Ends & Fun Begins!, vacation rental in Jamaica
Lands End Lodge on the Rappahannock River - Where the Road Ends & Fun Begins!, vacation rental in Jamaica
Lands End Lodge on the Rappahannock River - Where the Road Ends & Fun Begins!, vacation rental in Jamaica

Lands End Lodge on the Rappahannock River - Where the Road Ends & Fun Begins!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sail in! Paddle out! Dog-friendly 500' serene waterfront near Chesapeake Bay, vacation rental in Jamaica
Sail in! Paddle out! Dog-friendly 500' serene waterfront near Chesapeake Bay, vacation rental in Jamaica
Sail in! Paddle out! Dog-friendly 500' serene waterfront near Chesapeake Bay, vacation rental in Jamaica

Sail in! Paddle out! Dog-friendly 500' serene waterfront near Chesapeake Bay

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Jamaica
Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Jamaica
Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Jamaica

Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to 'A Shore Thing!'  Waterfront Apartment for Two, vacation rental in Jamaica
Welcome to 'A Shore Thing!'  Waterfront Apartment for Two, vacation rental in Jamaica
Welcome to 'A Shore Thing!'  Waterfront Apartment for Two, vacation rental in Jamaica

Welcome to 'A Shore Thing!' Waterfront Apartment for Two

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Our Private Peninsula, Cozy, Serene,Fire Pit,Fishing,Kayak, Canoe, Paddle Board, vacation rental in Jamaica
Our Private Peninsula, Cozy, Serene,Fire Pit,Fishing,Kayak, Canoe, Paddle Board, vacation rental in Jamaica
Our Private Peninsula, Cozy, Serene,Fire Pit,Fishing,Kayak, Canoe, Paddle Board, vacation rental in Jamaica

Our Private Peninsula, Cozy, Serene,Fire Pit,Fishing,Kayak, Canoe, Paddle Board

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rappahannock River Cottage Getaway near Tappahannock, Urbanna, Chesapeake Bay, vacation rental in Jamaica
Rappahannock River Cottage Getaway near Tappahannock, Urbanna, Chesapeake Bay, vacation rental in Jamaica
Rappahannock River Cottage Getaway near Tappahannock, Urbanna, Chesapeake Bay, vacation rental in Jamaica

Rappahannock River Cottage Getaway near Tappahannock, Urbanna, Chesapeake Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Upscale Private Cottage in the Charming Village of Irvington with Dock Access!, vacation rental in Jamaica
Upscale Private Cottage in the Charming Village of Irvington with Dock Access!, vacation rental in Jamaica
Upscale Private Cottage in the Charming Village of Irvington with Dock Access!, vacation rental in Jamaica

Upscale Private Cottage in the Charming Village of Irvington with Dock Access!

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Charming Waterfront Family Getaway On The Rappahannock, vacation rental in Jamaica
Charming Waterfront Family Getaway On The Rappahannock, vacation rental in Jamaica
Charming Waterfront Family Getaway On The Rappahannock, vacation rental in Jamaica

Charming Waterfront Family Getaway On The Rappahannock

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Rosegill near Urbanna, VA on Rappahannock River, vacation rental in Jamaica
Historic Rosegill near Urbanna, VA on Rappahannock River, vacation rental in Jamaica
Historic Rosegill near Urbanna, VA on Rappahannock River, vacation rental in Jamaica

Historic Rosegill near Urbanna, VA on Rappahannock River

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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The River House Getaway! Come Relax and Enjoy!, vacation rental in Jamaica
The River House Getaway! Come Relax and Enjoy!, vacation rental in Jamaica
The River House Getaway! Come Relax and Enjoy!, vacation rental in Jamaica

The River House Getaway! Come Relax and Enjoy!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Deep water dock on the beautiful Corrotoman River, vacation rental in Jamaica
Deep water dock on the beautiful Corrotoman River, vacation rental in Jamaica
Deep water dock on the beautiful Corrotoman River, vacation rental in Jamaica

Deep water dock on the beautiful Corrotoman River

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Private, Peaceful, UNBELIEVABLY Close To The River! Fish, Kayak and More!, vacation rental in Jamaica
NEW! Private, Peaceful, UNBELIEVABLY Close To The River! Fish, Kayak and More!, vacation rental in Jamaica
NEW! Private, Peaceful, UNBELIEVABLY Close To The River! Fish, Kayak and More!, vacation rental in Jamaica

NEW! Private, Peaceful, UNBELIEVABLY Close To The River! Fish, Kayak and More!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bring the Boat & Bikes to Our in Town Kilmarnock Home from $95 per night, vacation rental in Jamaica
Bring the Boat & Bikes to Our in Town Kilmarnock Home from $95 per night, vacation rental in Jamaica
Bring the Boat & Bikes to Our in Town Kilmarnock Home from $95 per night, vacation rental in Jamaica

Bring the Boat & Bikes to Our in Town Kilmarnock Home from $95 per night

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax On Rappahannock, in Urbanna, Not Only For Oyster Fest, * The Blue Tango!, vacation rental in Jamaica
Relax On Rappahannock, in Urbanna, Not Only For Oyster Fest, * The Blue Tango!, vacation rental in Jamaica
Relax On Rappahannock, in Urbanna, Not Only For Oyster Fest, * The Blue Tango!, vacation rental in Jamaica

Relax On Rappahannock, in Urbanna, Not Only For Oyster Fest, * The Blue Tango!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Enjoy Sunsets On The Creek In Your Own Private Paradise., vacation rental in Jamaica
Enjoy Sunsets On The Creek In Your Own Private Paradise., vacation rental in Jamaica
Enjoy Sunsets On The Creek In Your Own Private Paradise., vacation rental in Jamaica

Enjoy Sunsets On The Creek In Your Own Private Paradise.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Irvington Country Getaway House, vacation rental in Jamaica
Irvington Country Getaway House, vacation rental in Jamaica
Irvington Country Getaway House, vacation rental in Jamaica

Irvington Country Getaway House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shore Fun!  Perfect Waterfront Get-a-Way **New for 2019!  Hot Tub!**, vacation rental in Jamaica
Shore Fun!  Perfect Waterfront Get-a-Way **New for 2019!  Hot Tub!**, vacation rental in Jamaica
Shore Fun!  Perfect Waterfront Get-a-Way **New for 2019!  Hot Tub!**, vacation rental in Jamaica

Shore Fun! Perfect Waterfront Get-a-Way **New for 2019! Hot Tub!**

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront home with dock and study on 1.6 acres, vacation rental in Jamaica
Waterfront home with dock and study on 1.6 acres, vacation rental in Jamaica
Waterfront home with dock and study on 1.6 acres, vacation rental in Jamaica

Waterfront home with dock and study on 1.6 acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy family fun and Sunsets at Piankatank Point., vacation rental in Jamaica
Enjoy family fun and Sunsets at Piankatank Point., vacation rental in Jamaica
Enjoy family fun and Sunsets at Piankatank Point., vacation rental in Jamaica

Enjoy family fun and Sunsets at Piankatank Point.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Looking for a quiet waterfront cottage for 5 for a day, a week or longer?, vacation rental in Jamaica
Looking for a quiet waterfront cottage for 5 for a day, a week or longer?, vacation rental in Jamaica
Looking for a quiet waterfront cottage for 5 for a day, a week or longer?, vacation rental in Jamaica

Looking for a quiet waterfront cottage for 5 for a day, a week or longer?

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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River House looking at the Chesapeake Bay, vacation rental in Jamaica
River House looking at the Chesapeake Bay, vacation rental in Jamaica
River House looking at the Chesapeake Bay, vacation rental in Jamaica

River House looking at the Chesapeake Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Eastern Virginia's Premier Vacation Escape & Event Location, vacation rental in Jamaica
Eastern Virginia's Premier Vacation Escape & Event Location, vacation rental in Jamaica
Eastern Virginia's Premier Vacation Escape & Event Location, vacation rental in Jamaica

Eastern Virginia's Premier Vacation Escape & Event Location

Rental Home
5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Peaceful-Relaxing-Charming 1914 home-quaint town- fish-boat-bike-New listing, vacation rental in Jamaica
Peaceful-Relaxing-Charming 1914 home-quaint town- fish-boat-bike-New listing, vacation rental in Jamaica
Peaceful-Relaxing-Charming 1914 home-quaint town- fish-boat-bike-New listing, vacation rental in Jamaica

Peaceful-Relaxing-Charming 1914 home-quaint town- fish-boat-bike-New listing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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'The Keys Cottage' in the Woods In Irvington, vacation rental in Jamaica
'The Keys Cottage' in the Woods In Irvington, vacation rental in Jamaica
'The Keys Cottage' in the Woods In Irvington, vacation rental in Jamaica

'The Keys Cottage' in the Woods In Irvington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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My Blue Heaven on Hacks Creek!!!, vacation rental in Jamaica
My Blue Heaven on Hacks Creek!!!, vacation rental in Jamaica
My Blue Heaven on Hacks Creek!!!, vacation rental in Jamaica

My Blue Heaven on Hacks Creek!!!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Serene Sauna Retreat w/Chefs Kitchen & Luxury Bath, vacation rental in Jamaica
Serene Sauna Retreat w/Chefs Kitchen & Luxury Bath, vacation rental in Jamaica
Serene Sauna Retreat w/Chefs Kitchen & Luxury Bath, vacation rental in Jamaica

Serene Sauna Retreat w/Chefs Kitchen & Luxury Bath

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront 4 bedroom historic home on Rappahanock River with Dock, vacation rental in Jamaica
Waterfront 4 bedroom historic home on Rappahanock River with Dock, vacation rental in Jamaica
Waterfront 4 bedroom historic home on Rappahanock River with Dock, vacation rental in Jamaica

Waterfront 4 bedroom historic home on Rappahanock River with Dock

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Drop Anchor! Coastal Living secluded waterfront 2hr from DC Kayaks, SUPs 4BR/3BA, vacation rental in Jamaica
Drop Anchor! Coastal Living secluded waterfront 2hr from DC Kayaks, SUPs 4BR/3BA, vacation rental in Jamaica
Drop Anchor! Coastal Living secluded waterfront 2hr from DC Kayaks, SUPs 4BR/3BA, vacation rental in Jamaica

Drop Anchor! Coastal Living secluded waterfront 2hr from DC Kayaks, SUPs 4BR/3BA

Rental Home
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Country Ranch close to area historical attractions, vacation rental in Jamaica
Country Ranch close to area historical attractions, vacation rental in Jamaica
Country Ranch close to area historical attractions, vacation rental in Jamaica

Country Ranch close to area historical attractions

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charm & Privacy! In the heart of town. Walk to Tides Inn and Downtown Irvington!, vacation rental in Jamaica
Charm & Privacy! In the heart of town. Walk to Tides Inn and Downtown Irvington!, vacation rental in Jamaica
Charm & Privacy! In the heart of town. Walk to Tides Inn and Downtown Irvington!, vacation rental in Jamaica

Charm & Privacy! In the heart of town. Walk to Tides Inn and Downtown Irvington!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pop Castle- Historic Gem on the Rappahannock River, vacation rental in Jamaica
Pop Castle- Historic Gem on the Rappahannock River, vacation rental in Jamaica
Pop Castle- Historic Gem on the Rappahannock River, vacation rental in Jamaica

Pop Castle- Historic Gem on the Rappahannock River

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Location Location-Step directly out on N.Main Street to shopping & restaurants,, vacation rental in Jamaica
Location Location-Step directly out on N.Main Street to shopping & restaurants,, vacation rental in Jamaica
Location Location-Step directly out on N.Main Street to shopping & restaurants,, vacation rental in Jamaica

Location Location-Step directly out on N.Main Street to shopping & restaurants,

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Jamaica
Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Jamaica
Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Jamaica

Rappahannock River waterfront property for rent with Pier & Pool access

Rental Home
3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home with Pier, 2bds/1ba, vacation rental in Jamaica
Waterfront Home with Pier, 2bds/1ba, vacation rental in Jamaica
Waterfront Home with Pier, 2bds/1ba, vacation rental in Jamaica

Waterfront Home with Pier, 2bds/1ba

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BayCations!-Urbanna-Boating-Seafood-Golf-Wineries, vacation rental in Jamaica
BayCations!-Urbanna-Boating-Seafood-Golf-Wineries, vacation rental in Jamaica
BayCations!-Urbanna-Boating-Seafood-Golf-Wineries, vacation rental in Jamaica

BayCations!-Urbanna-Boating-Seafood-Golf-Wineries

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1 block off the River Romantic Apartment, vacation rental in Jamaica
1 block off the River Romantic Apartment, vacation rental in Jamaica
1 block off the River Romantic Apartment, vacation rental in Jamaica

1 block off the River Romantic Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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� Luxury Waterfront Retreat w/ Private Pool & Dock, vacation rental in Jamaica
� Luxury Waterfront Retreat w/ Private Pool & Dock, vacation rental in Jamaica
� Luxury Waterfront Retreat w/ Private Pool & Dock, vacation rental in Jamaica

� Luxury Waterfront Retreat w/ Private Pool & Dock

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Rosé Retreat at Vineyard Grove - Perfect for a romantic getaway!, vacation rental in Jamaica
The Rosé Retreat at Vineyard Grove - Perfect for a romantic getaway!, vacation rental in Jamaica
The Rosé Retreat at Vineyard Grove - Perfect for a romantic getaway!, vacation rental in Jamaica

The Rosé Retreat at Vineyard Grove - Perfect for a romantic getaway!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Jamaica