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Holiday Rentals in Dewey Beach

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266 rentals in Dewey Beach.
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A pet-friendly rental in the ocean block of North Dewey Beach!, holiday rental in Dewey Beach
A pet-friendly rental in the ocean block of North Dewey Beach!, holiday rental in Dewey Beach
A pet-friendly rental in the ocean block of North Dewey Beach!, holiday rental in Dewey Beach

A pet-friendly rental in the ocean block of North Dewey Beach!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Three Level Ocean Front Unit in popular Dewey Beach!, holiday rental in Dewey Beach
Three Level Ocean Front Unit in popular Dewey Beach!, holiday rental in Dewey Beach
Three Level Ocean Front Unit in popular Dewey Beach!, holiday rental in Dewey Beach

Three Level Ocean Front Unit in popular Dewey Beach!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lighthouse Cove Condo with bay view and great amenities!, holiday rental in Dewey Beach
Lighthouse Cove Condo with bay view and great amenities!, holiday rental in Dewey Beach
Lighthouse Cove Condo with bay view and great amenities!, holiday rental in Dewey Beach

Lighthouse Cove Condo with bay view and great amenities!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Three-Story Townhome with Community Pool Access, holiday rental in Dewey Beach
Three-Story Townhome with Community Pool Access, holiday rental in Dewey Beach
Three-Story Townhome with Community Pool Access, holiday rental in Dewey Beach

Three-Story Townhome with Community Pool Access

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Rare find! Immaculate and modern condo with a community pool! , holiday rental in Dewey Beach
Rare find! Immaculate and modern condo with a community pool! , holiday rental in Dewey Beach
Rare find! Immaculate and modern condo with a community pool! , holiday rental in Dewey Beach

Rare find! Immaculate and modern condo with a community pool!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanside Cozy Cottage 2 Blocks to Beach! Family & Dog Friendly! All Amenities!, holiday rental in Dewey Beach
Oceanside Cozy Cottage 2 Blocks to Beach! Family & Dog Friendly! All Amenities!, holiday rental in Dewey Beach
Oceanside Cozy Cottage 2 Blocks to Beach! Family & Dog Friendly! All Amenities!, holiday rental in Dewey Beach

Oceanside Cozy Cottage 2 Blocks to Beach! Family & Dog Friendly! All Amenities!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Adorable, Family-Friendly, Uniquely Comfortable, Walk to Beach, holiday rental in Dewey Beach
Adorable, Family-Friendly, Uniquely Comfortable, Walk to Beach, holiday rental in Dewey Beach
Adorable, Family-Friendly, Uniquely Comfortable, Walk to Beach, holiday rental in Dewey Beach

Adorable, Family-Friendly, Uniquely Comfortable, Walk to Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Block Townhouse With NEW Everything & Ocean Views, holiday rental in Dewey Beach
Beach Block Townhouse With NEW Everything & Ocean Views, holiday rental in Dewey Beach
Beach Block Townhouse With NEW Everything & Ocean Views, holiday rental in Dewey Beach

Beach Block Townhouse With NEW Everything & Ocean Views

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Renovated in 2022, 5BR, heated pool, firepit, garden oasis, character & charm!, holiday rental in Dewey Beach
Renovated in 2022, 5BR, heated pool, firepit, garden oasis, character & charm!, holiday rental in Dewey Beach
Renovated in 2022, 5BR, heated pool, firepit, garden oasis, character & charm!, holiday rental in Dewey Beach

Renovated in 2022, 5BR, heated pool, firepit, garden oasis, character & charm!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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40 yards from the beach, heat / ac splits, 4 season rental, pet friendly!, holiday rental in Dewey Beach
40 yards from the beach, heat / ac splits, 4 season rental, pet friendly!, holiday rental in Dewey Beach
40 yards from the beach, heat / ac splits, 4 season rental, pet friendly!, holiday rental in Dewey Beach

40 yards from the beach, heat / ac splits, 4 season rental, pet friendly!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stay Play Dewey - Oceanfront Dewey Beach Townhouse, holiday rental in Dewey Beach
Stay Play Dewey - Oceanfront Dewey Beach Townhouse, holiday rental in Dewey Beach
Stay Play Dewey - Oceanfront Dewey Beach Townhouse, holiday rental in Dewey Beach

Stay Play Dewey - Oceanfront Dewey Beach Townhouse

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury cottage, 7BR, heated pool, firepit, beach-block, character & charm!, holiday rental in Dewey Beach
Luxury cottage, 7BR, heated pool, firepit, beach-block, character & charm!, holiday rental in Dewey Beach
Luxury cottage, 7BR, heated pool, firepit, beach-block, character & charm!, holiday rental in Dewey Beach

Luxury cottage, 7BR, heated pool, firepit, beach-block, character & charm!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Luxury Condo With An Amazing Location & Views. 1 Block Away From The Beach!!, holiday rental in Dewey Beach
Luxury Condo With An Amazing Location & Views. 1 Block Away From The Beach!!, holiday rental in Dewey Beach
Luxury Condo With An Amazing Location & Views. 1 Block Away From The Beach!!, holiday rental in Dewey Beach

Luxury Condo With An Amazing Location & Views. 1 Block Away From The Beach!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front, Sunrise Views, Well Appointed, Delaware Beach, Rehoboth By The Sea, holiday rental in Dewey Beach
Ocean Front, Sunrise Views, Well Appointed, Delaware Beach, Rehoboth By The Sea, holiday rental in Dewey Beach
Ocean Front, Sunrise Views, Well Appointed, Delaware Beach, Rehoboth By The Sea, holiday rental in Dewey Beach

Ocean Front, Sunrise Views, Well Appointed, Delaware Beach, Rehoboth By The Sea

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Block in the Center of Dewey.  Large Deck Pets Allowed., holiday rental in Dewey Beach
Ocean Block in the Center of Dewey.  Large Deck Pets Allowed., holiday rental in Dewey Beach
Ocean Block in the Center of Dewey.  Large Deck Pets Allowed., holiday rental in Dewey Beach

Ocean Block in the Center of Dewey. Large Deck Pets Allowed.

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront Sights and Sounds! See and Hear the Ocean from Porch and Veranda, holiday rental in Dewey Beach
Oceanfront Sights and Sounds! See and Hear the Ocean from Porch and Veranda, holiday rental in Dewey Beach
Oceanfront Sights and Sounds! See and Hear the Ocean from Porch and Veranda, holiday rental in Dewey Beach

Oceanfront Sights and Sounds! See and Hear the Ocean from Porch and Veranda

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Rehoboth by the Sea Oceanfront Paradise!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Book Your Beach Vacation Now!, holiday rental in Dewey Beach
Book Your Beach Vacation Now!, holiday rental in Dewey Beach
Book Your Beach Vacation Now!, holiday rental in Dewey Beach

Book Your Beach Vacation Now!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Fall & Winter Openings!  BOOK NOW! One of the best kept secrets in Dewey Beach!!, holiday rental in Dewey Beach
Fall & Winter Openings!  BOOK NOW! One of the best kept secrets in Dewey Beach!!, holiday rental in Dewey Beach
Fall & Winter Openings!  BOOK NOW! One of the best kept secrets in Dewey Beach!!, holiday rental in Dewey Beach

Fall & Winter Openings! BOOK NOW! One of the best kept secrets in Dewey Beach!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Ocean Block Dewey Beach and Pet Friendly!, holiday rental in Dewey Beach
Ocean Block Dewey Beach and Pet Friendly!, holiday rental in Dewey Beach
Ocean Block Dewey Beach and Pet Friendly!, holiday rental in Dewey Beach

Ocean Block Dewey Beach and Pet Friendly!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Brand New-Complete Reno, holiday rental in Dewey Beach
Brand New-Complete Reno, holiday rental in Dewey Beach
Brand New-Complete Reno, holiday rental in Dewey Beach

Brand New-Complete Reno

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Come see beautiful fall sunsets over the bay! Amazing off season rates!, holiday rental in Dewey Beach
Come see beautiful fall sunsets over the bay! Amazing off season rates!, holiday rental in Dewey Beach
Come see beautiful fall sunsets over the bay! Amazing off season rates!, holiday rental in Dewey Beach

Come see beautiful fall sunsets over the bay! Amazing off season rates!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Renovated in 2020, 5BR, heated pool,
fire pit, character and charm!, holiday rental in Dewey Beach
Renovated in 2020, 5BR, heated pool,
fire pit, character and charm!, holiday rental in Dewey Beach
Renovated in 2020, 5BR, heated pool,
fire pit, character and charm!, holiday rental in Dewey Beach

Renovated in 2020, 5BR, heated pool, fire pit, character and charm!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Serenity Amid it All. Pet friendly, WiFi, outdoor shower, grill, holiday rental in Dewey Beach
Serenity Amid it All. Pet friendly, WiFi, outdoor shower, grill, holiday rental in Dewey Beach
Serenity Amid it All. Pet friendly, WiFi, outdoor shower, grill, holiday rental in Dewey Beach

Serenity Amid it All. Pet friendly, WiFi, outdoor shower, grill

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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ROOFTOP POOL&HOT TUB OPEN ALL YEAR!  BOOK YOUR FALL, WINTER OR SUMMER 2023 NOW!!, holiday rental in Dewey Beach
ROOFTOP POOL&HOT TUB OPEN ALL YEAR!  BOOK YOUR FALL, WINTER OR SUMMER 2023 NOW!!, holiday rental in Dewey Beach
ROOFTOP POOL&HOT TUB OPEN ALL YEAR!  BOOK YOUR FALL, WINTER OR SUMMER 2023 NOW!!, holiday rental in Dewey Beach

ROOFTOP POOL&HOT TUB OPEN ALL YEAR! BOOK YOUR FALL, WINTER OR SUMMER 2023 NOW!!

Holiday Rental House
15 bedrooms
10 bathrooms
Sleeps 32
Match: Sleeps
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The Best Location in Dewey Beach 'Baywinds', holiday rental in Dewey Beach
The Best Location in Dewey Beach 'Baywinds', holiday rental in Dewey Beach
The Best Location in Dewey Beach 'Baywinds', holiday rental in Dewey Beach

The Best Location in Dewey Beach 'Baywinds'

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Coming to the Beach in the Fall and Winter is Wonderful!, holiday rental in Dewey Beach
Coming to the Beach in the Fall and Winter is Wonderful!, holiday rental in Dewey Beach
Coming to the Beach in the Fall and Winter is Wonderful!, holiday rental in Dewey Beach

Coming to the Beach in the Fall and Winter is Wonderful!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Flexibility, Great Value 7 Bedrm, 4 Bath, Home, Beach 2 Blocks, holiday rental in Dewey Beach
Flexibility, Great Value 7 Bedrm, 4 Bath, Home, Beach 2 Blocks, holiday rental in Dewey Beach
Flexibility, Great Value 7 Bedrm, 4 Bath, Home, Beach 2 Blocks, holiday rental in Dewey Beach

Flexibility, Great Value 7 Bedrm, 4 Bath, Home, Beach 2 Blocks

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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78 Steps to the BEACH and three parking spots!!, holiday rental in Dewey Beach
78 Steps to the BEACH and three parking spots!!, holiday rental in Dewey Beach
78 Steps to the BEACH and three parking spots!!, holiday rental in Dewey Beach

78 Steps to the BEACH and three parking spots!!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Perfect Location Dewey Townhouse great Mon to Fri rate, holiday rental in Dewey Beach
Perfect Location Dewey Townhouse great Mon to Fri rate, holiday rental in Dewey Beach
Perfect Location Dewey Townhouse great Mon to Fri rate, holiday rental in Dewey Beach

Perfect Location Dewey Townhouse great Mon to Fri rate

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Fantastic Condo just one block to the beach!, holiday rental in Dewey Beach
Fantastic Condo just one block to the beach!, holiday rental in Dewey Beach
Fantastic Condo just one block to the beach!, holiday rental in Dewey Beach

Fantastic Condo just one block to the beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning California-style cottage, 2 minute walk to beach!!, holiday rental in Dewey Beach
Stunning California-style cottage, 2 minute walk to beach!!, holiday rental in Dewey Beach
Stunning California-style cottage, 2 minute walk to beach!!, holiday rental in Dewey Beach

Stunning California-style cottage, 2 minute walk to beach!!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Luxury Condo 1 block from the Beach!!  Great Location with Marina & Bay Views., holiday rental in Dewey Beach
Luxury Condo 1 block from the Beach!!  Great Location with Marina & Bay Views., holiday rental in Dewey Beach
Luxury Condo 1 block from the Beach!!  Great Location with Marina & Bay Views., holiday rental in Dewey Beach

Luxury Condo 1 block from the Beach!! Great Location with Marina & Bay Views.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean-block townhome in Dewey Beach, featuring a rooftop deck with ocean views!, holiday rental in Dewey Beach
Ocean-block townhome in Dewey Beach, featuring a rooftop deck with ocean views!, holiday rental in Dewey Beach
Ocean-block townhome in Dewey Beach, featuring a rooftop deck with ocean views!, holiday rental in Dewey Beach

Ocean-block townhome in Dewey Beach, featuring a rooftop deck with ocean views!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Elevator! Dog friendly! 2nd house from ocean., holiday rental in Dewey Beach
Elevator! Dog friendly! 2nd house from ocean., holiday rental in Dewey Beach
Elevator! Dog friendly! 2nd house from ocean., holiday rental in Dewey Beach

Elevator! Dog friendly! 2nd house from ocean.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Newly Decorated Beach Cottage- Steps To The Beach, holiday rental in Dewey Beach
Newly Decorated Beach Cottage- Steps To The Beach, holiday rental in Dewey Beach
Newly Decorated Beach Cottage- Steps To The Beach, holiday rental in Dewey Beach

Newly Decorated Beach Cottage- Steps To The Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Be the Envy of Those Walking by! Prime Location!, holiday rental in Dewey Beach
Be the Envy of Those Walking by! Prime Location!, holiday rental in Dewey Beach
Be the Envy of Those Walking by! Prime Location!, holiday rental in Dewey Beach

Be the Envy of Those Walking by! Prime Location!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful Home with a 3-Night Weekend Option!, holiday rental in Dewey Beach
Beautiful Home with a 3-Night Weekend Option!, holiday rental in Dewey Beach
Beautiful Home with a 3-Night Weekend Option!, holiday rental in Dewey Beach

Beautiful Home with a 3-Night Weekend Option!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Beautiful Dewey Beach Condo at the Opal, holiday rental in Dewey Beach
Beautiful Dewey Beach Condo at the Opal, holiday rental in Dewey Beach
Beautiful Dewey Beach Condo at the Opal, holiday rental in Dewey Beach

Beautiful Dewey Beach Condo at the Opal

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean Front beach house, holiday rental in Dewey Beach
Ocean Front beach house, holiday rental in Dewey Beach
Ocean Front beach house, holiday rental in Dewey Beach

Ocean Front beach house

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Luxury condo with bay views and walking distance to the beach., holiday rental in Dewey Beach
Luxury condo with bay views and walking distance to the beach., holiday rental in Dewey Beach
Luxury condo with bay views and walking distance to the beach., holiday rental in Dewey Beach

Luxury condo with bay views and walking distance to the beach.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Steps to Beach! Inground Pool, Roof Top Deck w/Ocean Views -2 Great Rooms!, holiday rental in Dewey Beach
Steps to Beach! Inground Pool, Roof Top Deck w/Ocean Views -2 Great Rooms!, holiday rental in Dewey Beach
Steps to Beach! Inground Pool, Roof Top Deck w/Ocean Views -2 Great Rooms!, holiday rental in Dewey Beach

Steps to Beach! Inground Pool, Roof Top Deck w/Ocean Views -2 Great Rooms!

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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DEWEY Beach Block Cottage on the Best Block in Dewey!, holiday rental in Dewey Beach
DEWEY Beach Block Cottage on the Best Block in Dewey!, holiday rental in Dewey Beach
DEWEY Beach Block Cottage on the Best Block in Dewey!, holiday rental in Dewey Beach

DEWEY Beach Block Cottage on the Best Block in Dewey!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean Block Single Family Home - 16a Dickinson, holiday rental in Dewey Beach
Ocean Block Single Family Home - 16a Dickinson, holiday rental in Dewey Beach
Ocean Block Single Family Home - 16a Dickinson, holiday rental in Dewey Beach

Ocean Block Single Family Home - 16a Dickinson

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Modern and well-kept condo in the heart of Dewey Beach!, holiday rental in Dewey Beach
Modern and well-kept condo in the heart of Dewey Beach!, holiday rental in Dewey Beach
Modern and well-kept condo in the heart of Dewey Beach!, holiday rental in Dewey Beach

Modern and well-kept condo in the heart of Dewey Beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Two 10 bdr/10 bath new construction resort homes to be built, open July 2023, holiday rental in Dewey Beach
Two 10 bdr/10 bath new construction resort homes to be built, open July 2023, holiday rental in Dewey Beach
Two 10 bdr/10 bath new construction resort homes to be built, open July 2023, holiday rental in Dewey Beach

Two 10 bdr/10 bath new construction resort homes to be built, open July 2023

Holiday Rental House
10 bedrooms
10 bathrooms
Sleeps 18
Match: Sleeps
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Dewey II Oceanblock 2BR., holiday rental in Dewey Beach
Dewey II Oceanblock 2BR., holiday rental in Dewey Beach
Dewey II Oceanblock 2BR., holiday rental in Dewey Beach

Dewey II Oceanblock 2BR.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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10 Chicago Street  - 10 Bedrooms - 91/2 Path Ocean Block w/ pool, holiday rental in Dewey Beach
10 Chicago Street  - 10 Bedrooms - 91/2 Path Ocean Block w/ pool, holiday rental in Dewey Beach
10 Chicago Street  - 10 Bedrooms - 91/2 Path Ocean Block w/ pool, holiday rental in Dewey Beach

10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool

Holiday Rental House
10 bedrooms
10 bathrooms
Sleeps 22
Match: Sleeps
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Enjoy the screened in porch just steps from the beach., holiday rental in Dewey Beach
Enjoy the screened in porch just steps from the beach., holiday rental in Dewey Beach
Enjoy the screened in porch just steps from the beach., holiday rental in Dewey Beach

Enjoy the screened in porch just steps from the beach.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Ocean View 4 BR End Unit Townhouse. End Unit, holiday rental in Dewey Beach
Ocean View 4 BR End Unit Townhouse. End Unit, holiday rental in Dewey Beach
Ocean View 4 BR End Unit Townhouse. End Unit, holiday rental in Dewey Beach

Ocean View 4 BR End Unit Townhouse. End Unit

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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