Holiday Rentals in Dickinson

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Our top choices for Dickinson holiday rentals

“Big Shirley” in Sunny San Leon

“Big Shirley” in Sunny San Leon
San Leon
10.0 out of 10, Exceptional, (1)
"Helpful owners"
United States
David
The price is €111
includes taxes & fees
29 Dec - 30 Dec
“Big Shirley” in Sunny San Leon

Peaceful Retreat with Texas-Shaped Pool

Peaceful Retreat with Texas-Shaped Pool
San Leon
10.0 out of 10, Exceptional, (1)
"We had a great time ! Wish we could have stayed longer . Beautiful property!"
United States
Carole N.
The price is €268
includes taxes & fees
18 Dec - 19 Dec
Peaceful Retreat with Texas-Shaped Pool

Galveston Bay House

Galveston Bay House
San Leon
10.0 out of 10, Exceptional, (32)
"The property was clean and conveniently close to a lot of attractions. We would love to stay there again. "
United States
Kristina Y.
The price is €257
includes taxes & fees
29 Dec - 30 Dec
Galveston Bay House

Cozy Coastal Cottage

Cozy Coastal Cottage
San Leon
10.0 out of 10, Exceptional, (32)
"We were back in the area to celebrate our wedding anniversary! We had lots of great food and fun!"
United States
Shannon H.
The price is €290
includes taxes & fees
22 Dec - 23 Dec
Cozy Coastal Cottage

Waterfront Bay Home with Pool & Private Pier

Waterfront Bay Home with Pool & Private Pier
2.0 star property
San Leon
The price is €286
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Bay Home with Pool & Private Pier

San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!

San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!
2.0 star property
San Leon
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! Jessica was very responsive and accommodating to all of our questions and needs. The place was very clean, organized and perfect for a short getaway. Enjoyed the use of the private pier for fishing and crabbing. Best of all we were lucky to see dolphins swimming right next to the pier and caught lots of fishes like sheep heads, red snappers and several crabs! We had a perfect stay and wished we could have stayed longer!!!"
United States
nguyen l.
The price is €274
includes taxes & fees
21 Dec - 22 Dec
San Leon, Galv Bay- 300' Private Pier w/ Green Fishing Lights! Immaculate home!

Stunning Home with Expansive Pool & Game Room

Stunning Home with Expansive Pool & Game Room
San Leon
8.8 out of 10, Excellent, (43)
"Everything was just like the pictures house has plenty of room we had 20 people there and it never felt crowded."
United States
Alan B.
Stunning Home with Expansive Pool & Game Room

Cozy Bay House w/ Hot Tub + Pier

Cozy Bay House w/ Hot Tub + Pier
San Leon
9.0 out of 10, Wonderful, (4)
"Great fishing trip!! "
United States
Jessica R.
Cozy Bay House w/ Hot Tub + Pier

Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston

Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston
San Leon
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay! The home was beautiful, clean and relaxing. The hosts were also wonderful to coordinate with. We will absolutely stay here again next year for our annual trip! "
United States
Taylor D.
The price is €322
includes taxes & fees
18 Dec - 19 Dec
Artistic & Charming 2-bedroom house on quiet lake near NASA and Galveston

Family-Friendly Retreat with Pool & Outdoor Lounge

Family-Friendly Retreat with Pool & Outdoor Lounge
2.0 star property
San Leon
The price is €344
includes taxes & fees
12 Jan - 13 Jan 2026
Family-Friendly Retreat with Pool & Outdoor Lounge

2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier

2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier
San Leon
10.0 out of 10, Exceptional, (1)
"The property is very comfortable and has all the amenities needed and then some. The kitchen is fully stocked, the appliances are first rate, and the furnishings are a great mix of modern and antiques. I felt like I was at home, not in a rental. The owner was very responsive to any questions I had while staying on the property. "
United States
Cindy B.
The price is €329
includes taxes & fees
15 Jan - 16 Jan 2026
2-bedroom 2 bath..4 beds total Amazing Waterfront condo w/310 ft lit pier

5-Acre Retreat with Heated Pool & Private Pond

5-Acre Retreat with Heated Pool & Private Pond
2.0 star property
San Leon
5-Acre Retreat with Heated Pool & Private Pond

Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!

Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!
2.0 star property
San Leon
The price is €127
includes taxes & fees
18 Dec - 19 Dec
Bella's Bungalow in Sunny San leon, TX. Come to escape and enjoy the Salt Life!

Bay Breeze Bungalow - Game Room & Pet Friendly

Bay Breeze Bungalow - Game Room & Pet Friendly
San Leon
9.2 out of 10, Wonderful, (5)
"Clean, quiet, check in and our process was simple. Location is great."
United States
Hannah L.
Bay Breeze Bungalow - Game Room & Pet Friendly

Lakefront Retreat Getaway Gameroom Firepit Fishing

Lakefront Retreat Getaway Gameroom Firepit Fishing
Dickinson
10.0 out of 10, Exceptional, (1)
"Grew up here in Dickinson. I never knew this beautiful view ever existed here! Quiet neighborhood, plenty of outdoor and indoor activities, close to church, clean and absolutely worth the price! I will return when I visit my family in a few months! So happy to have found this hidden gem!!!"
United States
René B.
Lakefront Retreat Getaway Gameroom Firepit Fishing

Waterfront Bay Views | Beautiful Private Pier

Waterfront Bay Views | Beautiful Private Pier
San Leon
10.0 out of 10, Exceptional, (21)
"Very clean place, great location and beautiful bat view would definitely stay at this place again in the future! "
United States
Ryan B.
The price is €470
includes taxes & fees
18 Dec - 19 Dec
Waterfront Bay Views | Beautiful Private Pier

Beautiful house with 4 bedrooms and 3 bathrooms

Beautiful house with 4 bedrooms and 3 bathrooms
Dickinson
8.0 out of 10, Very good, (16)
"Good place to stay"
United States
SAlly C.
The price is €343
includes taxes & fees
1 Jan - 2 Jan 2026
Beautiful house with 4 bedrooms and 3 bathrooms

Luxe Home 5 Bedroom Villa

Luxe Home 5 Bedroom Villa
League City
9.2 out of 10, Wonderful, (7)
"My group had a great stay at this property. The place was as described and the host was accommodating. Would stay here again if back in the area. "
United States
Conner C.
The price is €507
includes taxes & fees
18 Dec - 19 Dec
Luxe Home 5 Bedroom Villa

Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks

Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks
Dickinson
8.0 out of 10, Very good, (2)
"The house was very clean and comfortable! The master bed was very comfy. The only thing that was weird was there were no dressers. But that didn’t really affect us. Kids loved all the extra stuff and we loved staying right on the water. My husband enjoyed fishing and catching a few things. Nothing big, but at least he was able to fish on vacation. "
United States
Alvie May F.
The price is €361
includes taxes & fees
18 Dec - 19 Dec
Waterfront Retreat Getaway with Gameroom Firepit Fishing Kayaks

Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing

Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing
Dickinson
8.0 out of 10, Very good, (4)
"Beautiful house. Beautiful view of the bayou."
United States
Elizabeth T.
Dickinson Bayou Front Retreat Gateway Spacious 5-bedroom with Water view fishing
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dickinson Hotel Reviews

Find out more about Dickinson

Everything you need to know about Dickinson holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dickinson holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dickinson holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dickinson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dickinson. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dickinson holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dickinson holiday rentals we have selected for you start as low as €101 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dickinson rentals

At Expedia, we put the best Dickinson holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dickinson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dickinson holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dickinson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Dickinson?

Yes, there are holiday rentals in Dickinson close to Bay Area Raceway, or you can select a more secluded option if you're looking for a relaxing stay. Dickinson is known for its sporting events and shopping. Make sure you have time to check out the spas and restaurants during your trip.

What are some of the best holiday rentals that Dickinson has to offer?

Spacious Beach House, Pool & Huge Deck: This holiday home rental outside of Dickinson is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Dickinson?

With 74 Expedia holiday rentals, you're guaranteed to find just the right place for your Dickinson stay.

What can I see and do in Dickinson?

Cultural attractions include Dickinson Historic Railroad Center, whereas Bay Area Raceway is just one of the family-friendly sights. Other popular places to visit in the area include Port of Galveston Cruise Terminal and NASA Johnson Space Center.

What are holiday rentals like in Dickinson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dickinson. Holiday rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.