The Pines holiday rentals

We found 1,058 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select from 134 homes, 43 cottages and other holiday rentals in The Pines to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - The Pines

Showing deals for:7 Nov - 14 Nov

Large main living/dining/kitchen area with new appliances and all new furniture

Exceptional

(5 reviews)

4br/3ba + pool, close to beach. Pet friendly, WiFi, Parking, Quiet neighborhood

Rehoboth Beach, DE

8% off

AU$527 per night

includes taxes & fees

Exceptional

(19 reviews)

2 Bedroom Condo Henlopen Station w/ Brand New Bed

Rehoboth Beach, DE

8% off

AU$244 per night

includes taxes & fees

Exceptional

(99 reviews)

Beautiful downtown Rehoboth Beach townhouse - 3 blocks to the beach/boardwalk.

Rehoboth Beach, DE

8% off

AU$329 per night

includes taxes & fees

Welcome to "Going To Take A Boat Cottage" Key West of Rehoboth Beach!!!!

Exceptional

(56 reviews)

Key West Adorable Modern ONE B/R Cottage FOR TWO In Rehoboth Beach, Delaware

Rehoboth Beach, DE

8% off

AU$425 per night

includes taxes & fees

Exceptional

(29 reviews)

4br/2.5 bath, beach getaway, pool, pet friendly, close to beaches, restaurants

Rehoboth Beach, DE

8% off

AU$726 per night

includes taxes & fees

Exceptional

(107 reviews)

4-bedroom vacation home just 15-minute walk to Cape Henlopen State Park

Rehoboth Beach, DE

10% off

AU$453 per night

includes taxes & fees

Living area with centered stone gas fireplace between two sliding glass doors

Exceptional

(65 reviews)

Luxury Carriage House 4bd walking distance to downtown Rehoboth in Canal Corkran

Rehoboth Beach, DE

28% off

AU$496 per night

includes taxes & fees

Living room w/ charging stations on the side tables, and our community pool.

Exceptional

(33 reviews)

Beach House - POOL - Linens Provided - 2 Kings, 1 Queen, 3 Twins

Rehoboth Beach, DE

8% off

AU$493 per night

includes taxes & fees

Exceptional

(13 reviews)

Come to Fun & Friendly Rehoboth. Stay in the Center of all the fun Year Around!

Rehoboth Beach, DE

8% off

AU$582 per night

includes taxes & fees

Livingroom (with new pullout sofa - queen size)

Exceptional

(32 reviews)

Classic & Comfy dwtn Cottage, 1 block to the beach, screened porch, grill

Rehoboth Beach, DE

22% off

AU$757 per night

includes taxes & fees

Rehoboth Beach Vacation Rental | 2BR | 2BA | Stairs Required | 1,056 Sq Ft

Exceptional

(30 reviews)

2 Mi to Ocean: Rehoboth Beach Condo w/ Pool Access

Rehoboth Beach, DE

7% off

AU$287 per night

includes taxes & fees

Exceptional

(13 reviews)

Chic Beach Oasis in Heart of Rehoboth! Steps to Fine Dining and the Boardwalk!

Rehoboth Beach, DE

8% off

AU$445 per night

includes taxes & fees

Exceptional

(8 reviews)

BEAUTIFUL IN TOWN! - 2 Bedroom 1 Bath on Rehoboth Ave. Walk to Beach and Shops!

Rehoboth Beach, DE

8% off

AU$624 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find the best place to stay - The Pines

Convenient Rehoboth Beach in-town location

Sleeps 8 · 4 bedrooms · 1+ bathroom

47 Henlopen Avenue, Rehoboth Beach, Delaware

Sleeps 8 · 3 bedrooms · 2 bathrooms

Large 4 Bed/3 Bath House

Sleeps 8 · 4 bedrooms · 3 bathrooms

Family Beach House Steps to Beach Sleeps 10

Sleeps 10 · 5 bedrooms · 2 bathrooms

Kitchen features Jenn Air stainless steel appliances & large granite island.

Newly built home in the Pines downtown Rehoboth walk to beach, restaurants, shop

Sleeps 12 · 4 bedrooms · 4+ bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in The Pines?

The most desirable types of holiday homes in The Pines are houses. After something a little different? Stayz has a variety of options to match our guests' unique needs, so you'll see properties in loads of shapes and sizes. The perfect fit is waiting for you — grab yours today.

How much does it cost to rent a holiday home in The Pines?

Different factors can influence what you'll pay for your holiday home in The Pines, including the type of property, length of stay and season. But, all our holiday homes have something in common — excellent value. Just enter your travel dates to find your ideal escape.

How much does it cost to rent a beach house in The Pines?

The average price for a holiday home close to the beach in The Pines depends on when you'll be there and the size and style of property you're searching for. You can easily and quickly find prices on Stayz by entering your destination and travel dates. Then use the filter tool to pick the number of bedrooms and amenities that you need, like a pool, air conditioning and WiFi.

Are there pet-friendly holiday homes in The Pines?

Pack a travel bag and a bone for your pup because The Pines has 65 stays that throw out the welcome mat to doggie guests. Let your furriest pal get in on the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.

Can I rent a house with a pool in The Pines?

Grab your swimsuit and inflatable flamingo, because there are 13 houses with a private pool in The Pines. Kick back at one of these popular holiday homes and make every day a pool day. Simply enter your travel dates into Stayz, then check the "pool" filter to find the perfect place for a splashing good time!

What are popular home amenities in The Pines?

The most popular home amenities people are looking for in The Pines are a beach view, a lake view and a barbecue grill. Whether you're hitting the road with family, your besties or even pets, Stayz holiday homes have the best amenities for ultimate relaxation with the people that matter most.

Are there large group holiday homes in The Pines?

The Pines has 30 holiday properties that can host 10 or more guests. These stays come with the space you need to enjoy good times with loved ones.

Are there holiday homes in The Pines that welcome kids?

Gather your entire family for fun-filled adventures in The Pines at one of our 65 family-friendly holiday homes. Many of these stays provide conveniences that are ideal for trips with youngsters, like dining rooms, living rooms and outdoor spaces. Simply check the "Properties good for families" filter box and choose your favourite option.

What are the top attractions for families in The Pines?

Keeping the kiddos entertained during your stay in The Pines is a snap with these cool family-friendly attractions:

Rehoboth Beach
Funland
Jungle Jims River Safari Water Park

Are there one-bedroom holiday homes in The Pines?

The Pines has seven one-bedroom homes on offer. Typically located in sought-after areas thanks to their smaller size, a one-bedroom holiday home is ideal if you're travelling with your partner or a friend. And with comforts such as laundry facilities and more privacy than a standard hotel, you'll be able to kick back while exploring this fantastic destination.

Can I find two-bedroom holiday homes in The Pines?

Select from seven two-bedroom homes in The Pines. Give the kids the second room or fill it with a couple of your favourite people. There's a comfy spot for whoever's lucky enough to be coming along.

Are there holiday homes with WiFi in The Pines?

The Pines has 19 holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to updating your social media, these Stayz homes make it a breeze to get online.

How can I find holiday homes with air conditioning in The Pines?

The Pines has 63 holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To book a property on Stayz with this amenity, enter your travel dates and use the handy filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in The Pines?

The age limit can differ across properties on Stayz, so look at the rules of the holiday home in The Pines you want. But typically, it's 16, 18 or 21.

How long can I rent a holiday home in The Pines for?

The length of time you can book a holiday home in The Pines varies according to the property. Just enter your selected dates to view a list of options offering extended stays. With plenty of features such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find somewhere perfect to call your home away from home in The Pines.