Vacation Rentals By Owner In Dewey Beach, DE

Bayside cottage located in the heart of Dewey Beach featuring a large open living room, enclosed and screened porches, relaxing decks, private en suite bedroom, and plenty of off street parking!brbrBedroom 1: 1 King W/ 3/4 BathbrBedroom 2: 1 Queen W/ Half BathbrBedroom 3: 2 TwinbrOther: 1 Sofa Bed-porchbrbrGuests can purchase a USD70 (non-refundable) accidental damage protection fee policy OR select a USD3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Cottage

Charming Bayside Cottage in Dewey Beach: Relaxing Decks, Porches & Private Rooms

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$353.18

This spacious 1st floor Ocean Block apartment is just steps to the beach and close to everything in Dewey!brbrBedroom 1: 1 QueenbrBedroom 2: 2 TwinsbrOther: Double Sofabed SunroombrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Apartment

Spacious 1st Floor Ocean Block Apt, Steps to Beach & Close to Dewey

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$287.66

Glorious water views from this 2 bedroom 2 bath condo 3rd floor unit with elevator in the building located in Marina View - complex pool is right outside your door. Each spacious bedroom has a queen sized bed and a large 3/4 bath. Open kitchen, dining and living overlook the Rehoboth Bay....walk to downtown Dewey Beach and catch the Jolly Trolley to Rehoboth Beach for the boardwalk, shopping and dining.brbrBedroom 1: 1 Queen W/ 3/4 BathbrBedroom 2: 1 Queen W/ 3/4 BathbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.brThe standard policy for community pools is that they are opened starting on May 25th and closing on September 1st.

Glorious Water Views! 2BR/2BA Condo with Pool, Walk to Dewey & Trolley!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$896.45

Welcome to 9 New Orleans South, a 4 bedroom 3.5 bathroom 3-story twin which is just steps from the beach and a block from all the Dewey hotspots! This home features ocean views from both the living areas and owners suite, gourmet kitchen with 6-burner gas stove and 2 sinks, a covered porch, lower deck, and balconies. The owners suite on the 3rd floor showcases a vaulted ceiling with knotty pine bead board in both the bedroom and the attached office. There are 2 additional bedrooms and one hall bathroom on the third floor, as well as one en suite bedroom with private entrance and a European style bathroom on the first floor. An outdoor shower is also located on the first floor. Come, park your car, and walk or ride your bike to all the best that Dewey Beach has to offer! NEW FOR 2025-DOG FRIENDLY FOR ALL STAYS WITH ARRIVAL AFTER 8/16/25! NO BEACH WEEK OR GRADUATION CELEBRATIONS ARE PERMITTED. GUESTS WILL BE CHARGED A CANCELLATION FEE.brbrBedroom 1: 1 QueenbrBedroom 2: 1 DoublebrBedroom 3: 1 DoublebrBedroom 4: 1 QueenbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Beachside 4-Bedroom Retreat: Ocean Views, Gourmet Kitchen & Dog-Friendly

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

Exceptional(1)

$295.79

Beautiful two bedroom condominium with a large community pool located in the heart of Dewey Beach, just one block to the Ocean with one en-suite bedroom with a King Bed and one Bedroom with two twin beds with an adjacent hall bath, three Smart TVs, surround sound and gaming cable, walking distance to everything in town and a short Trolley ride to Rehoboth!brbrBedroom 1: 1 King W 3/4 BabrBedroom 2: 2 TwinsbrLiving Area: 1 Queen Sofa BedbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.brbrThe standard policy for community pools is that they are opened starting on May 25th and closing on September 1st.

Charming 2-Bedroom Condo in Dewey Beach, Pool, 1 Block to Ocean & Walk to Town!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$589.08

Ocean block FRIDAY TO FRIDAY rental property in Dewey Beach with rare Community Pool access included! This beautifully remodeled 4-bedroom, 3.5-bath coastal retreat offers the perfect beach getaway with stunning ocean and bay views from multiple decks and balconies. Situated within walking distance to Deweys vibrant restaurants, shops, and nightlife, this townhouse is just a short stroll to the sandy shores, making it ideal for those looking to enjoy both the ocean and the energetic charm of Dewey Beach. The main level features a bright and open-concept layout, complete with a modern, fully equipped kitchen, spacious dining area, and a cozy family room that leads out to both front and rear decks, perfect for relaxing after a day in the sun. The third level includes two guest rooms, two full baths, and a luxurious primary suite with a private balcony showcasing breathtaking views. On the first level, an additional guest suite offers privacy and direct access to a charming screened porch ideal for unwinding with a cool drink. Additional exterior highlights include covered parking, extra guest parking, and a convenient outdoor shower to rinse off after your beach adventures. Whether you are enjoying the pool, the beach, or the nearby activities, this townhouse offers everything you need for an unforgettable Dewey Beach vacation!brbrBedroom 1: 1 KingbrBedroom 2: 1 QueenbrBedroom 3: 1 DoublebrBedroom 4: 2 Twins/bunk BedbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.brThe standard policy for community pools is that they are opened starting on May 25th and closing on September 1st.

Beachside 4-BR Dewey Retreat w/ Pool Access, Ocean Views, and Walk to Shore!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

Exceptional(1)

$315.76

Enjoy the fabulous views from this 3rd floor Beach Front condominium featuring a full kitchen, living room with a picture window so you can relax and watch the Ocean and a Oceanfront deck. Perfect vacation spot!brbrBedroom 1: 1 QueenbrLiving Area: 1 Queen Sleep SofabrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Oceanfront 3rd Floor Condo with Stunning Views & Private Deck – Perfect Escape!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

Exceptional(3)

$459.85

This exceptional Dog Friendly 3 Bedroom 2 Bath Ocean Block home has been totally renovated and features a spacious open floor plan, large charming private deck. gorgeous outdoor shower, Dog run, fenced yard, and one car off street parking along with 2 Dewey Beach Parking Permits for use during your stay. Just steps to the sand and in the heart of Dewey Beach for nightlife and bay sports. Take a short Jolly Trolley ride to Rehoboth Beach for fine dining, shops or a stroll on the Boardwalk. NO BEACH WEEK OR GRADUATION CELEBRATIONS ARE PERMITTED. GUESTS WILL BE CHARGED A CANCELLATION FEE ( FOR VRBO RENTALS).brbrBedroom 1: QueenbrBedroom 2: Queen & TwinbrBedroom 3: DoublebrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Dog-Friendly 3BR Ocean Block Home w/ Deck, Fenced Yard & Steps to Sand!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$679.28

Ocean Front! Enjoy the fabulous views from this beautifully appointed end unit Dewey Beach townhouse. Located just steps from the sand, the many amenities include a new patio area with fire pit on the ground level, open concept living, dining and kitchen with deck and 1/2 bath on the 2nd floor, and the 3rd and 4th levels feature 2 bedrooms each with two more relaxing decks. There is a refreshing outside shower to use after your day at the beach, gas grill, and plenty of off street parking!brbrBedroom 1: 1 KingbrBedroom 2: 1 QueenbrBedroom 3: 1 QueenbrBedroom 4: 2 TwinsbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Oceanfront Dewey Beach Townhouse: Stunning Views, Fire Pit & 4 Bedrooms!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$546.68

Just steps to the Ocean and walking distance to everything in Dewey Beach this 2nd and 3rd Floor apartment with 2 decks is the perfect vacation spot!brbrBedroom 1: 1 QueenbrBedroom 2: 2 TwinsbrBedroom 3: 2 TwinsbrOther: 2 Double Sofa BedsbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Apartment

Steps to the Ocean! 3BR, 2 Decks, Walk to Everything in Dewey Beach!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$895.77

Welcome to Sunset Bay! Dog Friendly ($300 pet fee per dog, 2 dog max) and completely renovated this Beautiful Bay Front Duplex has Unbelievable Sunsets, a Spacious Open Living Area, 3 En-Suite Bedrooms with 1 King sized bed, 2 Queen sized beds, 2 Twins and a Bunk bed with a double bed on the bottom and a twin bed on the top along with a twin sized trundle bed. Four and one half bathrooms and plenty of Off Street Parking and relaxing decks making this property your perfect Beach Get-a-Way! Walk to anywhere in Dewey Beach for nightlife, just over a block to the ocean and hop on the Jolley Trolly to go into Rehoboth Beach to enjoy the boardwalk, the shops and some of the finest dining in the area.brbrBedroom 1: D/s Bunk And 1 Twin TrundlebrBedroom 2: 2 TwinsbrBedroom 3: 1 KingbrBedroom 4: 1 QueenbrBedroom 5: 1 QueenbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Sunset Bay Beach Getaway-Renovated, Spacious, Dog-Friendly&Steps to Dewey Beach

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$268.85

Nicely appointed condo with great views of the Marina and Rehoboth Bay located in South Dewey Beach! This rental features 1 bedroom with 1 King bed and sofa bed in the living area, 1 full bath with an open and spacious floor plan, two balconies, two car parking, beautiful Roof Top Community Pool, storage closet with Beach Items, indoor lounge area and spacious outdoor grilling area!brbrBedroom 1: 1 KingbrLiving Area: 1 Full Sofa BedbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.brThe standard policy for community pools is that they are opened starting on May 25th and closing on September 1st.

Charming 1-BDR Condo with Stunning Marina Views & Rooftop Pool at South Dewey

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$385.32

Enjoy the Ocean Views from this spacious three level townhome located just steps to the beach in South Dewey. Featuring multiple sun decks, two bedrooms and a bathroom on the 1st level, large open living, dining, kitchen and powder room on the 2nd level and two additional bedrooms, including an ensuite bedroom on the 3rd level. Rinse off in the outside shower after a relaxing day at the beach and park your cars in the private spaces provided so you can walk everywhere in town!brbrBedroom 1: 1 Queen - Bathroom In HallbrBedroom 2: 1 Queen With Bath (f)brBedroom 3: 2 TwinsbrBedroom 4: 2 Twins/ TrundlebrLiving Area: 1 Sleep SofabrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

DUNES REACH 2-Enjoy the Ocean Views from this spacious three level townhome

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$1924.72

Enjoy sweeping views of the Atlantic Ocean and the Rehoboth Bay from the large roof top deck of this luxurious, newly renovated home in Dewey Beach Delaware! The home is located just steps from private North Indian Beach, and features a private pool and hot tub in the back yard. Enjoy views of the ocean from the top floor of the home, which includes a great room, gourmet kitchen, and large primary bedroom with en suite spa bath and private balcony. The second floor of the home has another TV area, an additional primary bedroom with a king bed, en suite bath, sleeper sofa, and private balcony. Down the hall includes two bedrooms with balconies overlooking the pool, queen beds and a shared bathroom. The first level of the home features another primary bedroom with a king bed and en suite bath, a bunk room for four, and a queen bedroom and hall bathroom. This home truly has all the amenities such as two outdoor showers, two washer and dryers, ice maker, two beverage refrigerators, beach chairs, umbrellas, and a turf yard perfect for corn hole and other games. Please note, linens are not provided and there is a 4 night minimum in the shoulder season. Pool openings are not guaranteed in the off season, please confirm with your agent. Pool is open sometime in May and closes September 13 2025 (September can be added for additional fee).brbrBedroom 1: 1 King W/3/4 BathbrBedroom 2: 2 Twin & 1 Full(bunkw/trundle)brBedroom 3: 1 QueenbrBedroom 4: 1 QueenbrBedroom 5: 1 King & Sofa Bed W/ 3/4 BathbrBedroom 6: 1 QueenbrBedroom 7: 1 King W/full BathbrOther: HdtvbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Luxurious Dewey Beach Home: Ocean Views, Pool, Hot Tub & Near North Indian Beach

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$471.99

Charming dog Friendly cottage located just 2 1/2 blocks to the beach in beautiful Rehoboth by the Sea! The main part of the house has a spacious living and dining area, newly renovated galley kitchen, master bedroom with a King bed (2 twins together), and a full bath. Two other bedrooms are located off of the main screened porch with 2 twins and 2 sets of bunks (4 twins) and there is a 3/4 bath in the hallway. There is an enclosed outside shower with dressing area to rinse off after a day at the beach, parking for 3 cars, relaxing back deck with comfortable chairs and gas grill on rear deck with a private fenced in yard that is perfect for your dog and children. Hop on the Jolly Trolley to take you into downtown Rehoboth Beach or Dewey Beach!brbrBedroom 1: 1 King (2 Singles)brBedroom 2: 2 TwinsbrBedroom 3: 4 Twin Bunk BedsbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Dog-Friendly Beach Cottage, 2.5 Blocks to Rehoboth by the Sea!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$531.28

Just steps to the Ocean with spectacular ocean views located in the heart of Dewey Beach this duplex features a layout with bedrooms on the second floor and living room kitchen and dining area on the 3rd floor with plenty of parking and other amenities.brbrBedroom 1: 1 King/full BathroombrBedroom 2: 1 QueenbrBedroom 3: 1 Double/twin BunkbedbrOther: 2 Queen SofabedsbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Steps to Ocean! Stunning Views & Spacious Duplex in Heart of Dewey Beach

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$627.71

This 2 bedroom condo has 1 King in the en-suite bedroom and 2 Queens in the 2nd bedroom. Lake/Ocean Views. Rooftop pool and parking under the building. Entry card is needed to access building.brbrBedroom 1: 1 King W/ Full BathbrBedroom 2: 2 QueensbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.brbrThe standard policy for community pools is that they are opened starting on May 25th and closing on September 1st.

Stunning 2BR Condo with Lake/Ocean Views, Rooftop Pool & Parking

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$281.85

Enjoy the Ocean Views from this end unit townhouse just steps to the beach featuring:brbrBedroom 1: 1 QueenbrBedroom 2: 1 Queen With Full BathbrBedroom 3: 2 Twin With 3/4 BathbrBedroom 4: 2 TwinbrbrGuests can purchase a $70 (non-refundable) accidental damage protection fee policy OR select a $3,000 refundable security deposit.brRentals DO NOT INCLUDE toiletries, bed or bath linens, linen packages are available for purchase.brDogs are not permitted in our rental units unless otherwise indicated.

Oceanview End Unit Townhouse Steps to Beach – Spacious 4BR, Sleeps 8!

Dewey Beach, Delaware, United States

Bed

Bath

Sleeps

$887.5