Annapolis Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Annapolis

Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (325)
"We normally stay in Santa Cruz but I think we liked Bodega Bay better. The house was beautiful and right on the beach. Beautiful views and we were able to hear the ocean from our bedroom. Property was clean and beautiful."
Oceanfront - Hot Tub - Newly Remodeled Cottage
Spacious Yet Cozy Bodega Bay Experience!
8.8 out of 10, Excellent, (214)
"Comfortable and clean, easy to find and short walk to Duncan's landing for excellent sunset viewing every night."
Spacious Yet Cozy Bodega Bay Experience!
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, (271)
"We had a delightful time and enjoyed Jenner, hiking, restaurants and the home! Beautiful!"
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
9.8 out of 10, Exceptional, (302)
"Wonderful!"
Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
9.0 out of 10, Wonderful, (36)
"The property is set on a picturesque spot in SeaRanch. Beautiful ocean views. The home itself has lots of nice and unexpected touches (amazing water pressure, oyster knife, dog blankets). It also had a few cost reducing pieces that ranked it down a notch for me (one ply toilet paper and paper towels, super thin cloth towels). We did have an issue with wet towels upon arrival and the property management remedied it within the first 24 hours of our stay. The outdoor space was very useful and...
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
Point Arena Lighthouse
3.0 star property
9.6 out of 10, Exceptional, (85)
"Very well supplied and maintained "
The price is CA $258
CA $328 total
includes taxes & fees
Jun 23 - Jun 24
Point Arena Lighthouse
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
10.0 out of 10, Exceptional, (306)
"This property is exactly as described. The views are beautiful and host is simple to communicate with."
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
9.6 out of 10, Exceptional, (168)
"We had a great time in this lovely little house right on the river. The house is well appointed and close to the town center. The large property is so beautiful and peaceful. We will definitely stay here again!"
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Ocean view home with free WiFi, jetted tub and close beach access
9.0 out of 10, Wonderful, (105)
"Well stocked great property with incredible views! Wish we could have stayed longer. Definitely hope to return."
Ocean view home with free WiFi, jetted tub and close beach access
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
8.6 out of 10, Excellent, (29)
"Beautiful location. Very clean. Awesome if you had a dog!"
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.4 out of 10, Very good, (12)
"This property was perfect for our writing retreat! It was spacious and comfortable, and set in a beautiful location. Would absolutely stay again!"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
Contemporary coastal home with private hot tub, shared pool, & ocean views
8.4 out of 10, Very good, (100)
"overall quite nice. construction next door was minimal, BUT the closeness of the new structure really took away from the overall feel. i'm sure 5-6 established trees and a little time will soften this effect."
Contemporary coastal home with private hot tub, shared pool, & ocean views
Sunlit home near river with hot tub, washer/dryer, firepit - dogs OK
9.6 out of 10, Exceptional, (42)
"Everything about this little cottage in the redwoods along the creek was perfect. It was very quiet and peaceful although we were here during the week. And while there are neighbors to the left and right. One was very quiet and the other neighbors were not there. a very nice place to retreat."
Sunlit home near river with hot tub, washer/dryer, firepit - dogs OK
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach
9.8 out of 10, Exceptional, (13)
"Location is the highlight of this Gualala studio. The stairs faded quickly into the spectacular views. This is a special retreat from the ordinary. Miren is a fantastic host, her knowledge of the area, attention to detail & warm hospitality all a highlight of our stay. We spent 3 nights & explored nearby, but the Anchor Bay beach below this studio makes this location a place of pure contentment, no need to roam. We hope to return."
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
10.0 out of 10, Exceptional, (48)
"The home is beautiful, comfortable and well stocked. We enjoyed the dock, the hot tub and the lovely kitchen and dining areas. It was quiet and serene. Hope to return soon."
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, (91)
"We went here with a group of friends and had the most amazing time! We will absolutely be going back. The house was really considered and had everything we needed. Also, can't beat being right on the water!"
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
9.8 out of 10, Exceptional, (259)
"Girls trip to wine country. Perfect location and accommodations for 6 of us. Clare is super, we have stayed here twice."
SETTING PRIVATE 2 blk toTown/River/Beach-Lg Deck+SPA-Mini Golf+Tennis+Coast12 mi
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
9.0 out of 10, Wonderful, (51)
"We spent four nights in this great home. It's in a nice location on a very quiet cul-de-sac. Close to day hiking trails and Gualala for restaurants. Home was very well equiped - we cooked several meals without finding any missing household items. Hot tub works great...which is sometimes a rarity in rental homes. We would definitely stay here again."
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
Riverfront Home, close to beach and restaurants
10.0 out of 10, Exceptional, (93)
"We had a wonderful stay. The property was well taken care of (both lovely and clean) and the location was perfect! We look forward to revisiting as well as recommend this home to friends."
Riverfront Home, close to beach and restaurants
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (375)
"Our stay was wonderful! It was so relaxing and the ultimate renewal for us. The garden in the front was the first beautiful site and seeing the view of ocean as we walked up the driveway. We will be back again to make more memories. Thank you for opening your home to us."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Don't see what you're looking for?
See all available properties in Annapolis
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.

Annapolis Vacation Rental Travel Info

Other types of properties in Annapolis you may be interested in

Timber Cove Resort
3.5 star property
9.0 out of 10, Wonderful, (115)
"The resort is one of the nicer ones in the area, the front staff was super nice and upgraded our room to ocean view for a fair discount. Our original room had the bed in a loft and a hike down some loft type stairs to the bathroom... it would not have worked for us. The restaurant overpriced but then what isn't these days. The biggest complaint was the mattress was so saggy and old it was seriously the worst I've ever seen. They just put a pad on top to hide that fact. so for that alone it...
The price is CA $419
CA $526 total
includes taxes & fees
Jun 16 - Jun 17
Timber Cove Resort
Gualala Country Inn
2.5 star property
8.8 out of 10, Excellent, (688)
"Very happy with our room. Beds very comfortable. Would like to come back when it is cold enough to enjoy the fireplace heater. "
The price is CA $234
CA $259 total
includes taxes & fees
Jun 16 - Jun 17
Gualala Country Inn
Casa Secoya
2.5 star property
9.0 out of 10, Wonderful, (337)
"We enjoyed our stay. Staff was friendly and responsive."
The price is CA $200
CA $228 total
includes taxes & fees
Jun 26 - Jun 27
Casa Secoya
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Annapolis?

Yes, you can find vacation rentals near popular local attractions in Annapolis, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Annapolis?

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.: This vacation home rental near Annapolis is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a spa tub, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Annapolis?

While you're exploring the area, Gualala River and Pebble Beach are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Black Point Beach and Walk On Beach.

What’s a vacation rental in Annapolis like?

Vacation rentals are privately owned properties you can book for a long or short time in Annapolis. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for small groups.

Recent reviews of Annapolis properties
Expedia verified reviews