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Holiday Homes in Oyster Bay

Destination
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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
45 rentals in Oyster Bay.
Read our reviews and book while there's availability, holiday rental in Oyster Bay
Read our reviews and book while there's availability, holiday rental in Oyster Bay
Read our reviews and book while there's availability, holiday rental in Oyster Bay

Read our reviews and book while there's availability

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 Bdrm BEACHFRONT 30% off >7days 
Quiet Safe Centre Island Sunsets, holiday rental in Oyster Bay
5 Bdrm BEACHFRONT 30% off >7days 
Quiet Safe Centre Island Sunsets, holiday rental in Oyster Bay
5 Bdrm BEACHFRONT 30% off >7days 
Quiet Safe Centre Island Sunsets, holiday rental in Oyster Bay

5 Bdrm BEACHFRONT 30% off >7days Quiet Safe Centre Island Sunsets

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walk to Beach, Marina, parks, cafes, restaurants.  3 BD RM Apartment, holiday rental in Oyster Bay
Walk to Beach, Marina, parks, cafes, restaurants.  3 BD RM Apartment, holiday rental in Oyster Bay
Walk to Beach, Marina, parks, cafes, restaurants.  3 BD RM Apartment, holiday rental in Oyster Bay

Walk to Beach, Marina, parks, cafes, restaurants. 3 BD RM Apartment

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Spectacular Waterfront Retreat, holiday rental in Oyster Bay
Spectacular Waterfront Retreat, holiday rental in Oyster Bay
Spectacular Waterfront Retreat, holiday rental in Oyster Bay

Spectacular Waterfront Retreat

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, private woodland cottage with two bedrooms and stone patio for summer!, holiday rental in Oyster Bay
Secluded, private woodland cottage with two bedrooms and stone patio for summer!, holiday rental in Oyster Bay
Secluded, private woodland cottage with two bedrooms and stone patio for summer!, holiday rental in Oyster Bay

Secluded, private woodland cottage with two bedrooms and stone patio for summer!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Gold Coast Estate - Island Centre, holiday rental in Oyster Bay
Gold Coast Estate - Island Centre, holiday rental in Oyster Bay
Gold Coast Estate - Island Centre, holiday rental in Oyster Bay

Gold Coast Estate - Island Centre

Holiday Rental House
11 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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The following properties within 32 kms of Oyster Bay match all your filters:
Hamptons Style Living Walk to Cafe  Deck, holiday rental in Oyster Bay
Hamptons Style Living Walk to Cafe  Deck, holiday rental in Oyster Bay
Hamptons Style Living Walk to Cafe  Deck, holiday rental in Oyster Bay

Hamptons Style Living Walk to Cafe Deck

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Captain's Cottage - Cold Spring Harbor Water Views, holiday rental in Oyster Bay
Captain's Cottage - Cold Spring Harbor Water Views, holiday rental in Oyster Bay
Captain's Cottage - Cold Spring Harbor Water Views, holiday rental in Oyster Bay

Captain's Cottage - Cold Spring Harbor Water Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Resort style house for rent in Old Brookville. Minimum 3 nights stay!, holiday rental in Oyster Bay
Resort style house for rent in Old Brookville. Minimum 3 nights stay!, holiday rental in Oyster Bay
Resort style house for rent in Old Brookville. Minimum 3 nights stay!, holiday rental in Oyster Bay

Resort style house for rent in Old Brookville. Minimum 3 nights stay!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming 3B2B Home Upper Level, holiday rental in Oyster Bay
Charming 3B2B Home Upper Level, holiday rental in Oyster Bay
Charming 3B2B Home Upper Level, holiday rental in Oyster Bay

Charming 3B2B Home Upper Level

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Glen Cove Vacation Rental < 1 Mi to Downtown!, holiday rental in Oyster Bay
Glen Cove Vacation Rental < 1 Mi to Downtown!, holiday rental in Oyster Bay
Glen Cove Vacation Rental < 1 Mi to Downtown!, holiday rental in Oyster Bay

Glen Cove Vacation Rental < 1 Mi to Downtown!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunny/Cozy 1 Bdrm Apt, 1 Hr To NYC, holiday rental in Oyster Bay
Sunny/Cozy 1 Bdrm Apt, 1 Hr To NYC, holiday rental in Oyster Bay
Sunny/Cozy 1 Bdrm Apt, 1 Hr To NYC, holiday rental in Oyster Bay

Sunny/Cozy 1 Bdrm Apt, 1 Hr To NYC

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SECRET HIDEAWAY: LUXURY ***. STUDIO W/PRIV. ENTRN, holiday rental in Oyster Bay
SECRET HIDEAWAY: LUXURY ***. STUDIO W/PRIV. ENTRN, holiday rental in Oyster Bay
SECRET HIDEAWAY: LUXURY ***. STUDIO W/PRIV. ENTRN, holiday rental in Oyster Bay

SECRET HIDEAWAY: LUXURY ***. STUDIO W/PRIV. ENTRN

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ultra-Modern Studio | Near Hospital & NYCIM | WiFi, holiday rental in Oyster Bay
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi, holiday rental in Oyster Bay
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi, holiday rental in Oyster Bay

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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cozy and convenient apartment 1 min from train., holiday rental in Oyster Bay
cozy and convenient apartment 1 min from train., holiday rental in Oyster Bay
cozy and convenient apartment 1 min from train., holiday rental in Oyster Bay

cozy and convenient apartment 1 min from train.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Adorable Cottage with Water Views, Across the street from Prime & other eateries, holiday rental in Oyster Bay
Adorable Cottage with Water Views, Across the street from Prime & other eateries, holiday rental in Oyster Bay
Adorable Cottage with Water Views, Across the street from Prime & other eateries, holiday rental in Oyster Bay

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beachfront Summer Rental- Sea Cliff, holiday rental in Oyster Bay
Beachfront Summer Rental- Sea Cliff, holiday rental in Oyster Bay
Beachfront Summer Rental- Sea Cliff, holiday rental in Oyster Bay

Beachfront Summer Rental- Sea Cliff

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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THE OASIS * LONG ISLAND, holiday rental in Oyster Bay
THE OASIS * LONG ISLAND, holiday rental in Oyster Bay
THE OASIS * LONG ISLAND, holiday rental in Oyster Bay

THE OASIS * LONG ISLAND

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beach Home  w/ Private Beach Access just feet away, holiday rental in Oyster Bay
Beach Home  w/ Private Beach Access just feet away, holiday rental in Oyster Bay
Beach Home  w/ Private Beach Access just feet away, holiday rental in Oyster Bay

Beach Home w/ Private Beach Access just feet away

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beach house cottage steps to private beach in the heart of Bayville, holiday rental in Oyster Bay
Beach house cottage steps to private beach in the heart of Bayville, holiday rental in Oyster Bay
Beach house cottage steps to private beach in the heart of Bayville, holiday rental in Oyster Bay

Beach house cottage steps to private beach in the heart of Bayville

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Long Island Apartment w/ Balcony ~ 25 Mi to NYC, holiday rental in Oyster Bay
Long Island Apartment w/ Balcony ~ 25 Mi to NYC, holiday rental in Oyster Bay
Long Island Apartment w/ Balcony ~ 25 Mi to NYC, holiday rental in Oyster Bay

Long Island Apartment w/ Balcony ~ 25 Mi to NYC

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Glen Cove Home: Walk to Boardwalk + Dining!, holiday rental in Oyster Bay
Glen Cove Home: Walk to Boardwalk + Dining!, holiday rental in Oyster Bay
Glen Cove Home: Walk to Boardwalk + Dining!, holiday rental in Oyster Bay

Glen Cove Home: Walk to Boardwalk + Dining!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ideally Located Glen Cove Apartment!, holiday rental in Oyster Bay
Ideally Located Glen Cove Apartment!, holiday rental in Oyster Bay
Ideally Located Glen Cove Apartment!, holiday rental in Oyster Bay

Ideally Located Glen Cove Apartment!

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming New York Escape Near Central Park!, holiday rental in Oyster Bay
Charming New York Escape Near Central Park!, holiday rental in Oyster Bay
Charming New York Escape Near Central Park!, holiday rental in Oyster Bay

Charming New York Escape Near Central Park!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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120 foot walk to semiprivate beach New central air, holiday rental in Oyster Bay
120 foot walk to semiprivate beach New central air, holiday rental in Oyster Bay
120 foot walk to semiprivate beach New central air, holiday rental in Oyster Bay

120 foot walk to semiprivate beach New central air

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking Waterfront house, holiday rental in Oyster Bay
Breathtaking Waterfront house, holiday rental in Oyster Bay
Breathtaking Waterfront house, holiday rental in Oyster Bay

Breathtaking Waterfront house

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant private resort style North Shore home, holiday rental in Oyster Bay
Elegant private resort style North Shore home, holiday rental in Oyster Bay
Elegant private resort style North Shore home, holiday rental in Oyster Bay

Elegant private resort style North Shore home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious, secluded, unique Carriage House close to NYC and beach!, holiday rental in Oyster Bay
Spacious, secluded, unique Carriage House close to NYC and beach!, holiday rental in Oyster Bay
Spacious, secluded, unique Carriage House close to NYC and beach!, holiday rental in Oyster Bay

Spacious, secluded, unique Carriage House close to NYC and beach!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time, holiday rental in Oyster Bay
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time, holiday rental in Oyster Bay
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time, holiday rental in Oyster Bay

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Charming bungalow with AC and WiFi in fantastic Cold Spring Harbor., holiday rental in Oyster Bay
Charming bungalow with AC and WiFi in fantastic Cold Spring Harbor., holiday rental in Oyster Bay
Charming bungalow with AC and WiFi in fantastic Cold Spring Harbor., holiday rental in Oyster Bay

Charming bungalow with AC and WiFi in fantastic Cold Spring Harbor.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Two for One Luxury Home & Studio Pre Weddings, holiday rental in Oyster Bay
Two for One Luxury Home & Studio Pre Weddings, holiday rental in Oyster Bay
Two for One Luxury Home & Studio Pre Weddings, holiday rental in Oyster Bay

Two for One Luxury Home & Studio Pre Weddings

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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4 Bedroom House perfect for families! Near Beach!, holiday rental in Oyster Bay
4 Bedroom House perfect for families! Near Beach!, holiday rental in Oyster Bay
4 Bedroom House perfect for families! Near Beach!, holiday rental in Oyster Bay

4 Bedroom House perfect for families! Near Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family Home near NY Beach, Private Workspace by Zen Living, holiday rental in Oyster Bay
Family Home near NY Beach, Private Workspace by Zen Living, holiday rental in Oyster Bay
Family Home near NY Beach, Private Workspace by Zen Living, holiday rental in Oyster Bay

Family Home near NY Beach, Private Workspace by Zen Living

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxe Provincial Style Studio w/ Patio & Parking, holiday rental in Oyster Bay
Luxe Provincial Style Studio w/ Patio & Parking, holiday rental in Oyster Bay
Luxe Provincial Style Studio w/ Patio & Parking, holiday rental in Oyster Bay

Luxe Provincial Style Studio w/ Patio & Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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��SUNSATIONAL Locust Valley Village  Charmer�HIGH SPEED INTERNET!�, holiday rental in Oyster Bay
��SUNSATIONAL Locust Valley Village  Charmer�HIGH SPEED INTERNET!�, holiday rental in Oyster Bay
��SUNSATIONAL Locust Valley Village  Charmer�HIGH SPEED INTERNET!�, holiday rental in Oyster Bay

��SUNSATIONAL Locust Valley Village Charmer�HIGH SPEED INTERNET!�

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcoming Glen Cove Home ~ 1 Mi to Public Beach!, holiday rental in Oyster Bay
Welcoming Glen Cove Home ~ 1 Mi to Public Beach!, holiday rental in Oyster Bay
Welcoming Glen Cove Home ~ 1 Mi to Public Beach!, holiday rental in Oyster Bay

Welcoming Glen Cove Home ~ 1 Mi to Public Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Apartment on tree lined 2 acre estate. Close to beaches, farms and NYC., holiday rental in Oyster Bay
Private Apartment on tree lined 2 acre estate. Close to beaches, farms and NYC., holiday rental in Oyster Bay
Private Apartment on tree lined 2 acre estate. Close to beaches, farms and NYC., holiday rental in Oyster Bay

Private Apartment on tree lined 2 acre estate. Close to beaches, farms and NYC.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Retreat in special private water front surrounding-45 minutes from Manhattan., holiday rental in Oyster Bay
Retreat in special private water front surrounding-45 minutes from Manhattan., holiday rental in Oyster Bay
Retreat in special private water front surrounding-45 minutes from Manhattan., holiday rental in Oyster Bay

Retreat in special private water front surrounding-45 minutes from Manhattan.

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious One Bedroom suite, holiday rental in Oyster Bay
Spacious One Bedroom suite, holiday rental in Oyster Bay
Spacious One Bedroom suite, holiday rental in Oyster Bay

Spacious One Bedroom suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy retreat with fenced in yard—centrally located in the heart of Long Island., holiday rental in Oyster Bay
Cozy retreat with fenced in yard—centrally located in the heart of Long Island., holiday rental in Oyster Bay
Cozy retreat with fenced in yard—centrally located in the heart of Long Island., holiday rental in Oyster Bay

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2bed/2bath Beach Bungalow in Bayville, NY, holiday rental in Oyster Bay
2bed/2bath Beach Bungalow in Bayville, NY, holiday rental in Oyster Bay
2bed/2bath Beach Bungalow in Bayville, NY, holiday rental in Oyster Bay

2bed/2bath Beach Bungalow in Bayville, NY

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 3BR Near Huntington's Nightlife & Beach, holiday rental in Oyster Bay
Cozy 3BR Near Huntington's Nightlife & Beach, holiday rental in Oyster Bay
Cozy 3BR Near Huntington's Nightlife & Beach, holiday rental in Oyster Bay

Cozy 3BR Near Huntington's Nightlife & Beach

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Serene Haven: Stunning Yard, Pool, and Views by RedAwning, holiday rental in Oyster Bay
Serene Haven: Stunning Yard, Pool, and Views by RedAwning, holiday rental in Oyster Bay
Serene Haven: Stunning Yard, Pool, and Views by RedAwning, holiday rental in Oyster Bay

Serene Haven: Stunning Yard, Pool, and Views by RedAwning

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Four Levels of Family-sized Stylish Living w/ game rm, patio and large backyard, holiday rental in Oyster Bay
Four Levels of Family-sized Stylish Living w/ game rm, patio and large backyard, holiday rental in Oyster Bay
Four Levels of Family-sized Stylish Living w/ game rm, patio and large backyard, holiday rental in Oyster Bay

Four Levels of Family-sized Stylish Living w/ game rm, patio and large backyard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington, holiday rental in Oyster Bay
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington, holiday rental in Oyster Bay
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington, holiday rental in Oyster Bay

Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-45 of 45
Frequently Asked Questions about Oyster Bay