Photo by Julia
Caine Woods vacation rentals
We found 843 vacation rentals — enter your dates for availability
Find the perfect place for your stay in Caine Woods by choosing from 108 houses, 87 condos, and other vacation rentals. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Caine Woods
Showing deals for:Oct 10 - Oct 17
Image gallery for MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
1010 out of 10 rating
Exceptional
(10 reviews)
MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
Ocean City, MD
9% off
$11,151 for 7 nights
$11,151 for 7 nights
Price is $1,593
$1,593
All fees included
Image gallery for Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
1010 out of 10 rating
Exceptional
(18 reviews)
Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
Ocean City, MD
8% off
$3,008 for 7 nights
$3,008 for 7 nights
Price is $430
$430
All fees included
Image gallery for Large oceanblock beach home - Short walk to beach, shops & great restaurants!
1010 out of 10 rating
Exceptional
(6 reviews)
Large oceanblock beach home - Short walk to beach, shops & great restaurants!
Fenwick Island, DE
8% off
$3,835 for 7 nights
$3,835 for 7 nights
Price is $548
$548
All fees included
Image gallery for Luxe Family Home, Sleeps 10, Community Pool
1010 out of 10 rating
Exceptional
(16 reviews)
Luxe Family Home, Sleeps 10, Community Pool
Ocean City, MD
9% off
$3,768 for 7 nights
$3,768 for 7 nights
Price is $538
$538
All fees included
Image gallery for Large Waterfront Luxury Home .9 Mile to Beach
9.49.4 out of 10 rating
Exceptional
(48 reviews)
Large Waterfront Luxury Home .9 Mile to Beach
Selbyville, DE
9% off
$4,884 for 7 nights
$4,884 for 7 nights
Price is $698
$698
All fees included
Image gallery for Town House on the Bay with Water Views and Pool!
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Town House on the Bay with Water Views and Pool!
Ocean City, MD
17% off
$1,539 for 7 nights
$1,539 for 7 nights
Price is $220
$220
All fees included
Image gallery for Large Fenwick Island 6-Bedroom Home just steps from Delaware/Maryland Beaches
1010 out of 10 rating
Exceptional
(31 reviews)
Large Fenwick Island 6-Bedroom Home just steps from Delaware/Maryland Beaches
Fenwick Island, DE
8% off
$5,524 for 7 nights
$5,524 for 7 nights
Price is $789
$789
All fees included
Image gallery for Stunning Sunrise & Water View! 1 Mile to the Beach! Steps to Waterfront Dining!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Stunning Sunrise & Water View! 1 Mile to the Beach! Steps to Waterfront Dining!
Selbyville, DE
16% off
$5,183 for 7 nights
$5,183 for 7 nights
Price is $740
$740
All fees included
Image gallery for Your own OC Suite with Pool - Blocks to the Beach
1010 out of 10 rating
Exceptional
(8 reviews)
Your own OC Suite with Pool - Blocks to the Beach
Ocean City, MD
9% off
$2,889 for 7 nights
$2,889 for 7 nights
Price is $413
$413
All fees included
Image gallery for Walkable Waterfront Bayside Townhome with boat slip, pool, and green space!
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Walkable Waterfront Bayside Townhome with boat slip, pool, and green space!
Selbyville, DE
9% off
$3,955 for 7 nights
$3,955 for 7 nights
Price is $565
$565
All fees included
Image gallery for Relax Here in this quiet Beach house!
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Relax Here in this quiet Beach house!
Ocean City, MD
8% off
$1,558 for 7 nights
$1,558 for 7 nights
Price is $223
$223
All fees included
Image gallery for Just Imagine! Luxury Renovation, Gorgeous Beach View-Indoor Pool -The Marylander
1010 out of 10 rating
Exceptional
(15 reviews)
Just Imagine! Luxury Renovation, Gorgeous Beach View-Indoor Pool -The Marylander
Ocean City, MD
8% off
$2,339 for 7 nights
$2,339 for 7 nights
Price is $334
$334
All fees included
Image gallery for Oceanside Fun in Fenwick Island! Charming retreat steps from beach and pool
1010 out of 10 rating
Exceptional
(59 reviews)
Oceanside Fun in Fenwick Island! Charming retreat steps from beach and pool
Fenwick Island, DE
8% off
$3,408 for 7 nights
$3,408 for 7 nights
Price is $487
$487
All fees included
Image gallery for Completely Renovated Perfect Beachtown Escape for the Whole Family
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Completely Renovated Perfect Beachtown Escape for the Whole Family
Ocean City, MD
8% off
$1,150 for 7 nights
$1,150 for 7 nights
Price is $164
$164
All fees included
Image gallery for Direct Oceanfront at 129th St--2 BR--2 BA--Huge Deck--Recently Renovated
1010 out of 10 rating
Exceptional
(14 reviews)
Direct Oceanfront at 129th St--2 BR--2 BA--Huge Deck--Recently Renovated
Ocean City, MD
9% off
$2,477 for 7 nights
$2,477 for 7 nights
Price is $354
$354
All fees included
Image gallery for Private 3 Bed 2 Bath Beach House. Remodeled, short walk to beach, wifi & laundry
1010 out of 10 rating
Exceptional
(15 reviews)
Private 3 Bed 2 Bath Beach House. Remodeled, short walk to beach, wifi & laundry
Ocean City, MD
8% off
$3,204 for 7 nights
$3,204 for 7 nights
Price is $458
$458
All fees included
Image gallery for Ocean Front, North Ocean City, Maryland
1010 out of 10 rating
Exceptional
(41 reviews)
Ocean Front, North Ocean City, Maryland
Ocean City, MD
9% off
$3,003 for 7 nights
$3,003 for 7 nights
Price is $429
$429
All fees included
Image gallery for Beautiful North Ocean City Spacious Townhouse with Outstanding Ocean Views!!!!
1010 out of 10 rating
Exceptional
(48 reviews)
Beautiful North Ocean City Spacious Townhouse with Outstanding Ocean Views!!!!
Ocean City, MD
9% off
$3,641 for 7 nights
$3,641 for 7 nights
Price is $520
$520
All fees included
Image gallery for Coastal chic waterfront townhouse w/bayside sunsets.
1010 out of 10 rating
Exceptional
(33 reviews)
Coastal chic waterfront townhouse w/bayside sunsets.
Ocean City, MD
8% off
$1,907 for 7 nights
$1,907 for 7 nights
Price is $272
$272
All fees included
Image gallery for Best Oceanfront - North Ocean - 134th Street
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Best Oceanfront - North Ocean - 134th Street
Ocean City, MD
9% off
$2,707 for 7 nights
$2,707 for 7 nights
Price is $387
$387
All fees included
Image gallery for Cozy Beachside Condo a short walk to the sand
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cozy Beachside Condo a short walk to the sand
Ocean City, MD
7% off
$1,948 for 7 nights
$1,948 for 7 nights
Price is $278
$278
All fees included
Image gallery for Custom Direct Oceanfront Home with 3 Bedrooms, Summer Open
9.89.8 out of 10 rating
Exceptional
(132 reviews)
Custom Direct Oceanfront Home with 3 Bedrooms, Summer Open
Ocean City, MD
8% off
$2,053 for 7 nights
$2,053 for 7 nights
Price is $293
$293
All fees included
Image gallery for Cool | Calm | Cozy
1010 out of 10 rating
Exceptional
(14 reviews)
Cool | Calm | Cozy
Ocean City, MD
17% off
$2,201 for 7 nights
$2,201 for 7 nights
Price is $314
$314
All fees included
Image gallery for Ocean Front Directly On Beach Walk Out To The Sand
9.69.6 out of 10 rating
Exceptional
(39 reviews)
Ocean Front Directly On Beach Walk Out To The Sand
Ocean City, MD
6% off
$2,838 for 7 nights
$2,838 for 7 nights
Price is $405
$405
All fees included
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Caine Woods
High Tide @ Lighthouse Bay
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Spacious 2 Bedroom Condo with Hot Tub!
Sleeps 6 · 2 bedrooms · 2 bathrooms
2 Bdrm/2 Bath, Sleeps 6, Pool, Balcony, Wi-Fi, TVs
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Vacation in a Fabulous Ocean City Townhouse--Kid-Friendly
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
New Luxe Home Steps to Ocean, Baby-Friendly, Garage, 2600 sq.ft - Sleeps 12
Sleeps 12 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Bayside Blue is Bayfront splendor AND you can bring the Dog!
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Top rated rentals - Caine Woods
Amazing Daisy
1010 out of 10
Exceptionalexceptional
1 review(1 review)
This property met all our expectations! It was fully stocked and had everything. The location was perfect to get to OC restaurants and shops as well as Fenwick, Bethany, Dewey and Rehoboth!!
Mary R.
Stayed Jun 2025
Spacious, Fun and Perfect!
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
We had the best time! The house is spacious, clean and has EVERYTHING you need to enjoy a relaxing vacation! We will definitely be back!
Jen I.
Stayed Jun 2025
Awesome!
1010 out of 10
Exceptionalexceptional
1 review(1 review)
This was our families first trip to OCMD and it couldn't have been better! Thank you so much for letting us share your home!
Kevin H.
Stayed Jun 2025
Great stay.
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The house was very nice and we had no issues.
Will L.
Stayed Jun 2025
5 Star Rental
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
The property is clean, updated and in a quiet neighborhood. We love staying here, and the host is great! Check in/out process is very easy.
Kara K.
Stayed Jun 2025
Family vacation
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Property was very comfortable, clean and had everything you would need available. Quiet neighborhood and nice, clean pool was an added plus. Great communication throughout the visit was a plus. Will definitely be booking again. Thank you for the wonderful stay Seaside vacations.
J D.
Stayed Jun 2025
As described
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Large new property in close proximity to the beach. Great location! House was equipped with all required items.I would only consider to add kettle:-)
krystsina i.
Stayed Jun 2025
Great location and stay
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Maggie is a great host and the condo is a good spot for visiting OC
Zendelle John B.
Stayed May 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Find out more about Caine Woods
Frequently asked questions
What is the most popular type of vacation rental accommodation in Caine Woods?
Condos are the most popular type of vacation rental in Caine Woods, according to our data. Even if you've got something else in mind, Vrbo has properties in many shapes and sizes. Look over our options to find your ideal fit.
How much does it cost to rent a vacation rental in Caine Woods?
Length of stay, property type and time of year are some of the conditions that can determine the price of a vacation home. Simply add your travel dates to find your perfect match. From quaint country cottages to expansive villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Caine Woods?
Prices for beach houses in Caine Woods vary depending on the size and style of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Caine Woods?
Pack a suitcase for your pup because Caine Woods has 129 vacation rentals that roll out the welcome mat to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Caine Woods?
Add an extra layer of fun to your vacation by staying in one of the 48 houses with a private pool in Caine Woods. Use our search filter to find properties with pools on Vrbo, then spend leisurely days frolicking in a swimming pool that's all your own.
What are popular rental amenities in Caine Woods?
Some of the most popular rental amenities people are searching for in Caine Woods include tennis, a fireplace and a firepit. Whether you're taking a trip with friends, family or even pets, Vrbo vacation homes have the best amenities for beginning new traditions with the people that matter most.
Are there large group vacation rentals in Caine Woods?
Caine Woods has 21 vacation rentals that can fit 10 or more people. These stays come with the privacy and space you need to share good times with your favorite people.
Are there vacation rentals in Caine Woods that welcome kids?
Caine Woods has 124 family-friendly vacation rentals to pick from. And discovering a stay that welcomes little ones is simple with Vrbo's "Properties good for families" filter. Besides having the whole place to yourselves, you'll get amenities and perks such as extra bedrooms, kitchens and private pools.
Are there one-bedroom vacation rentals in Caine Woods?
Yes, you can choose from 23 one-bedroom rentals in Caine Woods. Whether you're searching for a cozy cottage or an upmarket condo, our one-bedroom properties are ideal if you don't require lots of room. One of the best parts about having your own pad? You won't need to share your getaway with strangers.
Can I find two-bedroom vacation rentals in Caine Woods?
You can select from 51 two-bedroom homes in Caine Woods. Give the kids the second room or fill it with a couple of your favorite people. There's ample space for whoever's lucky enough to be coming along.
Are there vacation rentals with WiFi in Caine Woods?
Whether you want to keep up with the news, reply to emails or update your social media, there are 28 vacation homes with WiFi in Caine Woods. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Caine Woods?
Caine Woods has 122 vacation rentals where you can chill out in air-conditioned comfort. To book a property on Vrbo offering this amenity, enter your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Caine Woods?
The minimum required age is typically 16, 18 or 21. It can vary between properties on Vrbo, so check the rules of your preferred Caine Woods stay before making a booking.
How long can I rent a vacation rental in Caine Woods for?
The amount of time you can stay in a Caine Woods vacation home for is down to the property. Just tap in your travel dates to browse options offering extended stays. They have the things you need to make your extended break more enjoyable and comfortable, like laundries and air conditioning. Some vacation homes might also offer weekly or monthly discounted prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Caine Woods?
In Caine Woods, you'll find some fantastic deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're planning a weekend escape or a few weeks away, we've got plenty of options to suit your style.