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Taylors Island Vacation Rentals

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50 rentals in Taylors Island.
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Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island

Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island
A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island
A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island

A Vacation Away From It All-Family And Pet Friendly

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island
Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island
Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island

Tidal Serenity- Remote Waterfront Home with dock

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island
Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island
Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island

Family and Pet-Friendly, Waterfront with Pier

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!, vacation rental in Taylors Island
6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!, vacation rental in Taylors Island
6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!, vacation rental in Taylors Island

6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Peaceful Multi-generational Waterfront  Retreat w/Pool, vacation rental in Taylors Island
Peaceful Multi-generational Waterfront  Retreat w/Pool, vacation rental in Taylors Island
Peaceful Multi-generational Waterfront  Retreat w/Pool, vacation rental in Taylors Island

Peaceful Multi-generational Waterfront Retreat w/Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, vacation rental in Taylors Island
SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, vacation rental in Taylors Island
SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, vacation rental in Taylors Island

SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Rental Home
7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Waterfront Rental on Fishing Creek, Cambridge, MD, vacation rental in Taylors Island
Waterfront Rental on Fishing Creek, Cambridge, MD, vacation rental in Taylors Island
Waterfront Rental on Fishing Creek, Cambridge, MD, vacation rental in Taylors Island

Waterfront Rental on Fishing Creek, Cambridge, MD

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Retreat on the Chesapeake, vacation rental in Taylors Island
Waterfront Retreat on the Chesapeake, vacation rental in Taylors Island
Waterfront Retreat on the Chesapeake, vacation rental in Taylors Island

Waterfront Retreat on the Chesapeake

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Harbor Cottage Vacation Rental, vacation rental in Taylors Island
Chesapeake Bay Harbor Cottage Vacation Rental, vacation rental in Taylors Island
Chesapeake Bay Harbor Cottage Vacation Rental, vacation rental in Taylors Island

Chesapeake Bay Harbor Cottage Vacation Rental

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, vacation rental in Taylors Island
Waterfront Family Retreat with Deepwater Dock, vacation rental in Taylors Island
Waterfront Family Retreat with Deepwater Dock, vacation rental in Taylors Island

Waterfront Family Retreat with Deepwater Dock

Rental Home
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL, vacation rental in Taylors Island
BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL, vacation rental in Taylors Island
BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL, vacation rental in Taylors Island

BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Best Kept Secret By the Bay, vacation rental in Taylors Island
Best Kept Secret By the Bay, vacation rental in Taylors Island
Best Kept Secret By the Bay, vacation rental in Taylors Island

Best Kept Secret By the Bay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island

5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40

Rental Home
12 bedrooms
9 bathrooms
Sleeps 40
Match: Sleeps
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Waterfront, 23 Private Acres, Dock & Pool

Rental Home
4 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Very Private 2 Acre Waterfront Family Retreat with Pool and Pier, vacation rental in Taylors Island
Very Private 2 Acre Waterfront Family Retreat with Pool and Pier, vacation rental in Taylors Island
Very Private 2 Acre Waterfront Family Retreat with Pool and Pier, vacation rental in Taylors Island

Very Private 2 Acre Waterfront Family Retreat with Pool and Pier

Rental Home
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Our Always Dreaming Cottage - The Bay At Your Back Steps, vacation rental in Taylors Island
Our Always Dreaming Cottage - The Bay At Your Back Steps, vacation rental in Taylors Island
Our Always Dreaming Cottage - The Bay At Your Back Steps, vacation rental in Taylors Island

Our Always Dreaming Cottage - The Bay At Your Back Steps

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, vacation rental in Taylors Island
Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, vacation rental in Taylors Island
Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, vacation rental in Taylors Island

Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island
Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island
Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island

Waterfront Family Retreat with Pool on 7+ acres!

Rental Home
10 bedrooms
7 bathrooms
Sleeps 24
Match: Sleeps
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Harwood Cottage on Church Creek, waterfront, vacation rental in Taylors Island
Harwood Cottage on Church Creek, waterfront, vacation rental in Taylors Island
Harwood Cottage on Church Creek, waterfront, vacation rental in Taylors Island

Harwood Cottage on Church Creek, waterfront

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River, vacation rental in Taylors Island
Waterfront Getaway on the Choptank River, vacation rental in Taylors Island
Waterfront Getaway on the Choptank River, vacation rental in Taylors Island

Waterfront Getaway on the Choptank River

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW VACATION HOME !!!!, vacation rental in Taylors Island
NEW VACATION HOME !!!!, vacation rental in Taylors Island
NEW VACATION HOME !!!!, vacation rental in Taylors Island

NEW VACATION HOME !!!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cottage at Heron Cove, Chesapeake Bay, Cambridge, vacation rental in Taylors Island
Cottage at Heron Cove, Chesapeake Bay, Cambridge, vacation rental in Taylors Island
Cottage at Heron Cove, Chesapeake Bay, Cambridge, vacation rental in Taylors Island

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island
BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island
BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island

BayDreams - IronMan/Eagleman Retreat on the bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Estate on Bay / Fam. Reunions / Slps 28, vacation rental in Taylors Island
Year Round Estate on Bay / Fam. Reunions / Slps 28, vacation rental in Taylors Island
Year Round Estate on Bay / Fam. Reunions / Slps 28, vacation rental in Taylors Island

Year Round Estate on Bay / Fam. Reunions / Slps 28

Rental Home
7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Rental Home
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Quiet Woodland cottage near St. Leonard's Creek, vacation rental in Taylors Island
Quiet Woodland cottage near St. Leonard's Creek, vacation rental in Taylors Island
Quiet Woodland cottage near St. Leonard's Creek, vacation rental in Taylors Island

Quiet Woodland cottage near St. Leonard's Creek

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Chesapeake Waterfront Retreat with Pool, vacation rental in Taylors Island
Chesapeake Waterfront Retreat with Pool, vacation rental in Taylors Island
Chesapeake Waterfront Retreat with Pool, vacation rental in Taylors Island

Chesapeake Waterfront Retreat with Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming and Cozy with a Waterview, vacation rental in Taylors Island
Charming and Cozy with a Waterview, vacation rental in Taylors Island
Charming and Cozy with a Waterview, vacation rental in Taylors Island

Charming and Cozy with a Waterview

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bay Water Cottage - Private Bayfront Retreat from the World!, vacation rental in Taylors Island
Bay Water Cottage - Private Bayfront Retreat from the World!, vacation rental in Taylors Island
Bay Water Cottage - Private Bayfront Retreat from the World!, vacation rental in Taylors Island

Bay Water Cottage - Private Bayfront Retreat from the World!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island
Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island
Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island

Quarterdeck at Swan Cove Manor

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, vacation rental in Taylors Island
The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, vacation rental in Taylors Island
The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, vacation rental in Taylors Island

The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Best kept secret by the bay (Entire House), vacation rental in Taylors Island
Best kept secret by the bay (Entire House), vacation rental in Taylors Island
Best kept secret by the bay (Entire House), vacation rental in Taylors Island

Best kept secret by the bay (Entire House)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Outrigger at Swan Cove Manor, vacation rental in Taylors Island
Outrigger at Swan Cove Manor, vacation rental in Taylors Island
Outrigger at Swan Cove Manor, vacation rental in Taylors Island

Outrigger at Swan Cove Manor

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge, vacation rental in Taylors Island
Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge, vacation rental in Taylors Island
Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge, vacation rental in Taylors Island

Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, vacation rental in Taylors Island
Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, vacation rental in Taylors Island
Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, vacation rental in Taylors Island

Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!

Rental Home
7 bedrooms
6 bathrooms
Sleeps 24
Match: Sleeps
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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Hudson Manor - Multi-Family Waterfront Compound, Pool, Beach Volleyball!, vacation rental in Taylors Island
Hudson Manor - Multi-Family Waterfront Compound, Pool, Beach Volleyball!, vacation rental in Taylors Island
Hudson Manor - Multi-Family Waterfront Compound, Pool, Beach Volleyball!, vacation rental in Taylors Island

Hudson Manor - Multi-Family Waterfront Compound, Pool, Beach Volleyball!

Rental Home
7 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
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Monasterevin - Spacious Waterfront Home on 110-Acre Estate, Pets Welcome!, vacation rental in Taylors Island
Monasterevin - Spacious Waterfront Home on 110-Acre Estate, Pets Welcome!, vacation rental in Taylors Island
Monasterevin - Spacious Waterfront Home on 110-Acre Estate, Pets Welcome!, vacation rental in Taylors Island

Monasterevin - Spacious Waterfront Home on 110-Acre Estate, Pets Welcome!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spring Is Here, Come Explore Fossils and One Mile of Beach, vacation rental in Taylors Island
Spring Is Here, Come Explore Fossils and One Mile of Beach, vacation rental in Taylors Island
Spring Is Here, Come Explore Fossils and One Mile of Beach, vacation rental in Taylors Island

Spring Is Here, Come Explore Fossils and One Mile of Beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Business or Leisure?, vacation rental in Taylors Island
Business or Leisure?, vacation rental in Taylors Island
Business or Leisure?, vacation rental in Taylors Island

Business or Leisure?

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island

Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quiet cottage on wooded property, vacation rental in Taylors Island
Quiet cottage on wooded property, vacation rental in Taylors Island
Quiet cottage on wooded property, vacation rental in Taylors Island

Quiet cottage on wooded property

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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White Heron Inn 2565 Old House Point Rd, vacation rental in Taylors Island
White Heron Inn 2565 Old House Point Rd, vacation rental in Taylors Island
White Heron Inn 2565 Old House Point Rd, vacation rental in Taylors Island

White Heron Inn 2565 Old House Point Rd

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront glass house with private beach, vacation rental in Taylors Island
Waterfront glass house with private beach, vacation rental in Taylors Island
Waterfront glass house with private beach, vacation rental in Taylors Island

Waterfront glass house with private beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!, vacation rental in Taylors Island
Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!, vacation rental in Taylors Island
Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!, vacation rental in Taylors Island

Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!

Rental Home
7 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Breathtaking Waterfront Cambridge Getaway, vacation rental in Taylors Island
Breathtaking Waterfront Cambridge Getaway, vacation rental in Taylors Island
Breathtaking Waterfront Cambridge Getaway, vacation rental in Taylors Island

Breathtaking Waterfront Cambridge Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Mariner at Swan Cove Manor, vacation rental in Taylors Island
Mariner at Swan Cove Manor, vacation rental in Taylors Island
Mariner at Swan Cove Manor, vacation rental in Taylors Island

Mariner at Swan Cove Manor

Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Frequently Asked Questions about Taylors Island