US $253/Night
7 Nights - US $1,773
Annapolis Holiday Rentals
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Compare Villas, Resorts, & Rentals in Annapolis
House
10.0(1 Review)
1 Bedroom
4 Guests
Parking
Internet
Security/Safety
Guest Services
US $199/Night
7 Nights - US $1,391
US $200/Night
7 Nights - US $1,400
Cabin
9.8(57 Reviews)
2 Bedrooms
12 Guests
Oceanfront- Parking
Ocean View
Balcony/Terrace
US $559/Night
7 Nights - US $3,912
House
3 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
Child Friendly
Sports/Activities
US $280/Night
7 Nights - US $1,960
Cabin
9.4(6 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
Air Conditioner- Child Friendly
Bedding/Linens
US $252/Night
7 Nights - US $1,764
House
10.0(18 Reviews)
3 Bedrooms
8 Guests
Hot Tub- Parking
- Balcony/Terrace
Kitchen
US $352/Night
7 Nights - US $2,464
House
9.0(19 Reviews)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $503/Night
7 Nights - US $3,523
Cabin
8.8(12 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $443/Night
7 Nights - US $3,100
Luxury Holiday Rentals in Annapolis
Over 39+ Luxury Holiday Rentals in or Near Annapolis
US $619/Night
7 Nights - US $4,333
Cabin
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $383/Night
7 Nights - US $2,679
Cabin
10.0(8 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $339/Night
7 Nights - US $2,375
Cabin
9.0(8 Reviews)
1 Bedroom
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $304/Night
7 Nights - US $2,128
Cabin
9.8(36 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $303/Night
7 Nights - US $2,121
New
House
9.4(17 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $300/Night
7 Nights - US $2,101
Cabin
10 Bedrooms
10 Guests
- Parking
Pet Friendly- Child Friendly
- Security/Safety
US $285/Night
7 Nights - US $1,995
Cabin
10.0(2 Reviews)
3 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,939
Cabin
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $272/Night
7 Nights - US $1,906
Top-Rated Holiday Rentals with a Pool in Annapolis
Over 1+ The Best Private Villas and Holiday Rentals in Annapolis with a Pool
US $136/Night
7 Nights - US $955
Pet-Friendly Holiday Rentals in Annapolis
Over 13+ Pet-Friendly Holiday Rentals in or Near Annapolis
Cabin
9.6(86 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $206/Night
7 Nights - US $1,445
Cabin
9.0(6 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Pet Friendly
US $179/Night
7 Nights - US $1,254
Cabin
9.6(41 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $243/Night
7 Nights - US $1,701
Cabin
9.6(7 Reviews)
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $230/Night
7 Nights - US $1,607
Cabin
9.4(63 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,456
Cottage
9.4(16 Reviews)
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $180/Night
7 Nights - US $1,262
Cabin
9.2(5 Reviews)
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,512
Cabin
8.0(6 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $236/Night
7 Nights - US $1,652
Cabin
7.8(29 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $196/Night
7 Nights - US $1,369
Large Holiday Rentals and Private Villas in Annapolis
Over 3+ Large Holiday Rentals and Private Villas in or Near Annapolis
House
9.8(31 Reviews)
8 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $617/Night
7 Nights - US $4,317
Cabin
9.6(38 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $166/Night
7 Nights - US $1,162
House
3 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $193/Night
7 Nights - US $1,351
Annapolis Private Villas and Holiday Homes Under $200
Over 13+ Annapolis Private Villas and Holiday Homes Under $200
House
9.8(31 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,016
US $200/Night
7 Nights - US $1,400
Cabin
9.8(8 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $193/Night
7 Nights - US $1,352
House
7.2(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $192/Night
7 Nights - US $1,344
New
Cabin
1 Bedroom
8 Guests
- Air Conditioner
- Child Friendly
- Security/Safety
US $150/Night
7 Nights - US $1,052
Cabin
10.0(27 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $171/Night
7 Nights - US $1,195
House
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,102
Cabin
10.0(3 Reviews)
1 Bedroom
4 Guests
- Child Friendly
US $104/Night
7 Nights - US $728
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Child Friendly
US $124/Night
7 Nights - US $868
Instantly Bookable Holiday Homes in Annapolis
Over 2+ Instantly Bookable Holiday Homes in or Near Annapolis
New
Cabin
1 Bedroom
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $230/Night
7 Nights - US $1,607
Cabin
1 Bedroom
4 Guests
- Air Conditioner
- Child Friendly
- Security/Safety
US $86/Night
7 Nights - US $603
Book a Last Minute Place to Stay in Annapolis
About Casai's Private Villas and Holiday Rentals in Annapolis
Discover more than 48 vacation rentals available in Annapolis. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Annapolis.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Annapolis, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Annapolis. On average, places to stay near Annapolis offer 367.3 ft², with nightly prices averaging US $256.
With Casai, finding and comparing holiday rentals in Annapolis is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Annapolis, MO
There are 48 Annapolis, MO Holiday Rentals
- Prices for a holiday home in Annapolis start at US $136
- Top rated vacation home in Annapolis is Black River Retreat 5 Minutes from Jeff’s Canoe Rental/K Bridge
- Most popular short term in Annapolis is Rustic River Cabin Getaway
- Cheapest place to stay in Annapolis is Black River Motel and Restaurant
- Most expensive holiday rental in Annapolis is Sam A Baker
Recently Booked Holiday Rentals in Annapolis
Frequently Asked Questions About Annapolis?
What are the top holiday rentals in Annapolis?
With numerous options available in Annapolis, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Annapolis:
- Black River Retreat 5 Minutes from Jeff’s Canoe Rental/K Bridge
- Hidden Hollow Lodge. Peaceful 3-bedroom lodge on a private lake.
- Alpaca Farm Stay
- Secluded Underground Cabin in Ozarks Wilderness
- Riverfront Retreat w/Porch & Views in Des Arc!
- Hunters/Floaters Welcome! Creekside Missouri Cabin
- Mtn-View Cabin w/Deck & Fire Pit in Des Arc!
- Make your reservation fast as inquiries are coming in daily.
- Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.
- Secluded Log Cabin
Which holiday homes in Annapolis are best for families?
If you're searching for a family-friendly holiday home in Annapolis, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Annapolis:
How many Casai.com holiday rentals are available in Annapolis?
As of 2026, Casai boasts over 48 properties listed in the Annapolis area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Annapolis.
