Rehoboth ranked No. 2 for Happiest Seaside Town

We are now accepting 2026 off-season and summer vacation rental reservations! Contact us today for more information.

Availability and pricing will vary.

Featured Homes
Featured Rentals
New Listings
Open Houses
Just Closed

Residential
$899,000 3 bed • 2 bath • 1 hf ba

2578 Williamsville Rd, Houston, DE

MLS Dekt2044072

Residential
$379,900 3 bed • 2 bath

304 Holland St, Milton, DE

MLS Desu2106734

Residential
$1,065,000 4 bed • 3 bath

18383 Highwood Dr, Rehoboth Beach, DE

MLS Desu2092226

Residential
$1,449,000 5 bed • 4 bath

901 Savannah Rd, Lewes, DE

MLS Desu2104442

Residential
$745,000 1 bath

307 S Boardwalk #605, Rehoboth Beach, DE

MLS Desu2106052

IMG_6071 Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$1,575.00/week

14 CALVERT STREET

Ocean View

CLOSE TO MANY GOLF COURSES! AVAILABLE 3-4 NIGHTS OFF SEASON!

Book Now!

IMG_4350 Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$3,200.00/week

45 BROOKLYN AVENUE

South Rehoboth Beach

PHOTOS COMING SOON! UNDER RENOVATIONS!

Book Now!

91+Columbia Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$5,500.00/week

91 COLUMBIA AVENUE

The Pines Beach

BEAUTIFUL HOME IN THE PINES AREA!

Book Now!

9noext Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$3,645.00/week

9 NEW ORLEANS STREET

Dewey Beach

DOG FRIENDLY FOR STAYS BEGINNING 8/17/26!

Book Now!

C02B17A6-39C5-4814-87A7-74F12A9D9722 Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$1,490.00/week

21083 LAGUNA DRIVE

Surrounding Rehoboth and Dewey

Book Now!

shoalsign Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$2,300.00/week

33521 SCHOONER DRIVE

Surrounding Rehoboth and Dewey

BEAUTIFUL TOWNHOUSE AVAILABLE OFF SEASON $300/NIGHT!

Book Now!

2024+Aug+Front Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$3,030.00/week

5 BROAD HOLLOW

Henlopen Acres Beach

Book Now!

17aext Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$4,150.00/week

17A CLAYTON STREET

Dewey Beach

Book Now!

026_img_9270_783 Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$2,695.00/week

1600 BAYARD AVENUE

Dewey Beach

DOG FRIENDLY!

Book Now!

3501+Brandt+St+Living+1a Rehoboth ranked No. 2 for Happiest Seaside Town - Jack Lingo REALTOR

Starting at
$1,000.00/week

17059 S Brandt St. #3105

Surrounding Lewes

Book Now!

Residential
$3,500,000 3 bed • 2 bath • 1 hf ba

94 Tidewaters Rd, Rehoboth Beach, DE

MLS Desu2107752

Residential
$2,649,000 5 bed • 3 bath • 1 hf ba

130 East Side Dr, Rehoboth Beach, DE

MLS Desu2106828

Residential
$565,000 1 bed • 1 bath

11 Newbold Sq #11, Rehoboth Beach, DE

MLS Desu2107266

Residential
$3,290,000 5 bed • 3 bath • 1 hf ba

21 Cedar Rd, Rehoboth Beach, DE

MLS Desu2106054

Residential
$1,596,000 5 bed • 3 bath • 1 hf ba

41243 Gloucester Dr, Rehoboth Beach, DE

MLS Desu2106964

Residential
$1,148,679 3 bed • 2 bath • 1 hf ba

21767 Eastbridge Loop, Lewes, DE

Sold 03/17/2026

Residential
$1,085,701 4 bed • 3 bath

21781 Eastbridge Loop, Lewes, DE

Sold 03/17/2026

Residential
$652,000 3 bed • 2 bath • 1 hf ba

2805 American Eagle Way #5, Rehoboth Beach, DE

Sold 03/16/2026

Residential
$6,700,000 6 bed • 6 bath • 2 hf ba

12 Rolling Rd, Rehoboth Beach, DE

Sold 03/12/2026

Residential
$1,025,000 3 bed • 2 bath

57 Delaware Ave #b, Rehoboth Beach, DE

Sold 03/06/2026

Residential
$869,000 5 bed • 3 bath

27434 S Nicklaus Ave #76, Millsboro, DE

MLS Desu2082132

Open House
Date: 03/21/2026
11:00 AM - 02:00 PM

Additional Information: Hosted by Zane Jones, REALTOR® | 302-227-3883 (office) | 302-470-7669 (cell)

Residential
$1,590,000 5 bed • 5 bath • 1 hf ba

20157 W Piney Grove Rd, Georgetown, DE

MLS Desu2106196

Open House
Date: 03/21/2026
11:00 AM - 01:00 PM

Additional Information: Hosted by Shawn McDonnell, REALTOR® | 302-645-2007 (office) | 302-542-8591 (cell)

Residential
$1,065,000 4 bed • 3 bath

18383 Highwood Dr, Rehoboth Beach, DE

MLS Desu2092226

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM

Additional Information: Hosted by Merritt Cooch, REALTOR® | 302-645-2207 (office) | 302-562-7954 (cell)

Residential
$319,900 3 bed • 2 bath • 1 hf ba

29479 Whitstone Lane #1002, Millsboro, DE

MLS Desu2092936

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM
Date: 03/28/2026
12:00 PM - 02:00 PM

Additional Information: Hosted by Gary Brittingham, REALTOR® | 302-934-3970 (office) | 302-745-5605 (cell)

Residential
$1,195,000 4 bed • 3 bath

18116 Highwood Dr #131, Rehoboth Beach, DE

MLS Desu2101778

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM
Date: 03/22/2026
12:00 PM - 02:00 PM

Additional Information: Hosted by Carly Meluney, REALTOR® | 302-645-2207 (office) | 215-266-6336 (cell)

Residential
$4,295,000 5 bed • 5 bath • 1 hf ba

3 Laurel St, Rehoboth Beach, DE

MLS Desu2087390

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM
Date: 04/11/2026
12:00 AM - 02:00 PM

Additional Information: Hosted by Jordan Geyer, REALTOR® | 302-227-3883 (office) | 302-745-8286 (cell)

Residential
$535,000 3 bed • 2 bath

5 Radcliffe Dr, Rehoboth Beach, DE

MLS Desu2105820

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM

Additional Information: Hosted by Ava Cannon Team | 302-227-3883 (office) | 302-249-5620 (cell)

Residential
$565,000 1 bed • 1 bath

11 Newbold Sq #11, Rehoboth Beach, DE

MLS Desu2107266

Open House
Date: 03/21/2026
12:00 PM - 02:00 PM

Additional Information: Hosted by Lucius Webb, REALTOR® | 302-227-3883 (office) | 302-258-4590 (cell)

Residential
$319,900 2 bed • 2 bath

1400 Pebble Dr #1403, Rehoboth Beach, DE

MLS Desu2107208

Open House
Date: 03/21/2026
01:00 PM - 03:00 PM

Additional Information: Hosted by Molly Bayard Brittingham, REALTOR® | 302-337-3883 (office) | 302-381-0839 (cell)

Residential
$2,715,000 4 bed • 3 bath

701 Bayard Ave, Rehoboth Beach, DE

MLS Desu2106266

Open House
Date: 03/22/2026
11:00 AM - 02:00 PM

Additional Information: Hosted by Zane Jones, REALTOR® | 302-227-3883 (office) | 302-470-7669 (cell)

Residential
$2,649,000 5 bed • 3 bath • 1 hf ba

130 East Side Dr, Rehoboth Beach, DE

MLS Desu2106828

Open House
Date: 03/22/2026
11:00 AM - 01:00 PM

Additional Information: Hosted by Riess Livaudais, REALTOR® | 302-645-2207 (office) | 410-205-0184 (cell)

We Make Real Estate a Day at the Beach

Jack Lingo, REALTOR® is a family-owned-and-operated Delaware real estate business that focuses on representing all home buyers and sellers equally, fairly, and with the utmost integrity. Our licensed Delaware sales and rental agents are the best of the best, making us the leader in Delaware real estate sales and rentals at the beach. Our highly qualified agents are eager to assist you with the purchase of residential or commercial land in Delaware and look forward to helping you find the perfect Rehoboth Beach, Dewey Beach, or Lewes vacation home. Feel free to visit any of our open houses in Rehoboth Beach, Dewey Beach, Lewes, Bethany Beach, Millsboro, or the rest of Sussex County. Browse our listings now!

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Rehoboth ranked No. 2 for Happiest Seaside Town

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DOWNTOWN LEWES & THE BEACHES

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Everyone I have met within the Lingo organization has been a "cut above."Satisfied Client

The Realty team was excellent and check-in and check-out was super easy.Satisfied Client

Thank you for making check-in and check-out process easy and organized!Satisfied Client

Good morning ...once again you and your team facilitated a great vacation stay. We truly appreciate both you and the Lingo team and the property owner patiently working with us through the long pandemic saga.

Stay well and we look forward to seeing you again...Satisfied Client

We were so happy with this home! Every room felt fresh and updated, the pool was beautiful and the neighborhood was lovely and quiet. It was an easy walk to the beach and Rehoboth Ave, and fun to ride bikes through Cape Henlopen State Park. The home is stunning!VRBO Review

Testimonials

The Best Beach Vacation Rentals

On behalf of Jack Lingo, REALTOR'S® entire rental team, thank you for your interest in staying with us during your 2025 visit to Southern Delaware. With offices located in Rehoboth Beach, Lewes, and Millsboro, Delaware, you have plenty of excellent options from which to choose when searching for a vacation home.

We are proud of our rental team's consistent dedication to customer service. It is this pride that has helped us to remain the most trusted professionals in Coastal Delaware real estate rentals for over 50 years. From inland bay cottages to oceanfront homes and condos, we boast an abundance of vacation properties to suit your needs.

We Make Real Estate a Day at the Beach

Rehoboth ranked No. 2 for Happiest Seaside Town

Rehoboth ranked No. 2 for Happiest Seaside Town

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Karen Maull

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