Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (390)
"Perfect for a quiet getaway"
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is CA $82
CA $93 total
includes taxes & fees
Aug 5 - Aug 6
The Ranch at Lake Sonoma

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (443)
"The house is lovely and perfecty located for us with our dog to enjoy walks on the beach! We especially loved the view (of course) and the garden area in the front. It was the perfect getaway location. We plan on making this a yearly stay. "
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Point Arena Lighthouse

3.0 star property
9.6 out of 10, Exceptional, (105)
"The 2 bedroom house was newly remodeled. Very comfortable. Our window overlooked the ocean, front and back and the lighthouse."
The price is CA $247
CA $315 total
includes taxes & fees
Aug 7 - Aug 8
Point Arena Lighthouse

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (331)
"We enjoyed the lovely location, comfortable living spaces and fun decor even though the weather wasn’t perfect. Great place to relax."
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach

9.6 out of 10, Exceptional, (54)
"BEAUTIFUL VIEWS, QUIET AND PEACEFUL."
Oceanfront Studio with views of the Pacific Ocean & Direct Access to the Beach

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (151)
"We had a great stay, well stocked kitchen, loved the garden, the kids really enjoyed the pool!"
Luxurious Large Home, Beautiful Pool, Extensive Gardens

The Tiny Tipsy Turtle

2.0 star property
10.0 out of 10, Exceptional, (24)
"Love the location and all turtle theme"
The price is CA $186
CA $338 total
includes taxes & fees
Aug 6 - Aug 7
The Tiny Tipsy Turtle

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (385)
"Our third stay and first time booking three nights which seems to be the sweet spot for an extended weekend since you get two full days to relax along the coast. Already can't wait to book our next visit to this charming property!"
Oceanfront - Hot Tub - Newly Remodeled Cottage

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.

9.8 out of 10, Exceptional, (337)
"This is our second time at this property. It’s clean, well-located, and comfortable. I particularly liked the short explanations posted at key spots informing visitors why following instructions is beneficial for everyone. "
Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (6)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views

9.0 out of 10, Wonderful, (51)
"Excellent location with stunning ocean views. Ideal for family vacations."
Dog-friendly beach house with private hot tub, indoor pool, WiFi & ocean views

Sea Pine | Hot Tub with Ocean View

2.0 star property
9.2 out of 10, Wonderful, (52)
"Great, cozy home right on the bluffs. We loved the hot tub and well-stocked kitchen! "
Sea Pine | Hot Tub with Ocean View

Oceanfront home with private hot tub, views, & close beach access

9.2 out of 10, Wonderful, (95)
"The view and sound of the ocean cannot be beat! House was very clean at check-in. The beds were very comfortable."
Oceanfront home with private hot tub, views, & close beach access

Peaceful Redwood Hideaway - Hot Tub, A/C, Walk to Russian River and Downtown

10.0 out of 10, Exceptional, (39)
"Very nice place to visit and close to our favorite winery "
The price is CA $385
CA $711 total
includes taxes & fees
Aug 18 - Aug 19
Peaceful Redwood Hideaway - Hot Tub, A/C, Walk to Russian River and Downtown

Oceanview house with enclosed private yard - dog friendly

2.0 star property
8.0 out of 10, Very good, (4)
"Beautiful view. Awesome kitchen."
Oceanview house with enclosed private yard - dog friendly

Unbelievable Russian River Views ~ 3 Bed ~ 3 Bath ~ Pool~ Hot Tub +Tesla Charger

10.0 out of 10, Exceptional, (22)
"We had a wonderful visit! Gorgeous views. "
Unbelievable Russian River Views ~ 3 Bed ~ 3 Bath ~ Pool~ Hot Tub +Tesla Charger

Panoramic Ocean Views, Hot Tub Under The Stars

9.8 out of 10, Exceptional, (89)
"Clean and comfortable with everything we needed... the perfect stay for the four of us. We also enjoyed seeing the deers, rabbits, and turkeys around the house. We had a great time and would definitely stay again! "
Panoramic Ocean Views, Hot Tub Under The Stars

RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..

10.0 out of 10, Exceptional, (250)
"Beautiful home and surroundings. Well-appointed kitchen. Great communication with owner. Will return in June along with some warmer weather."
RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do..

Abalone Point: Oceanside Panoramic View Home

9.8 out of 10, Exceptional, (142)
"This property and host was so lovely- we had the best time celebrating my mom's 70th birthday. Fantastic kitchen, great little casita out back, hot tub, views... everything you need! Will be back soon. "
Abalone Point: Oceanside Panoramic View Home
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 Annapolis Hotel Reviews

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?

Point Arena Lighthouse: This vacation home rental near Annapolis is located by the ocean and has a private yard, a selection of games, and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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 Sea Ranch Golf Links.

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.