Estia Villas - Vacation Rentals in Annapolis
9.6
(
10 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1345.49 ft²
-
Private Beach -
Oceanfront -
Fireplace/Heating -
Ocean View
US $624
/Night
7 Nights - $4,369
Villa
8 Bedrooms
6 Bathrooms
16 Guests
14000 ft²
-
Private Pool -
Hot Tub -
Spa -
Fireplace/Heating
US $3,295
/Night
7 Nights - $23,065
7.8
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
10634.74 ft²
-
View -
Pet Friendly -
Parking -
Air Conditioner
US $114
/Night
7 Nights - $798
Villa
9.2
(
43 Reviews
)
4 Bedrooms
4 Bathrooms
6 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $555
/Night
7 Nights - $3,883
Villa
4 Bedrooms
3 Bathrooms
8 Guests
3229.17 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $585
/Night
7 Nights - $4,095
New
Villa
3 Bedrooms
2 Bathrooms
6 Guests
1905.21 ft²
-
Parking
-
Air Conditioner
-
Internet -
Child Friendly
US $326
/Night
7 Nights - $2,282
See More Annapolis Vacation Rentals
Luxury Places to Stay in Annapolis
Over 1360+
Luxury Places to Stay in or Near Annapolis
Boat Rental
6 Bedrooms
6 Bathrooms
12 Guests
-
Oceanfront
-
Ocean View
-
View
-
Kitchen
US $3,138
/Night
7 Nights - $21,969
House
10.0
(
27 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2900 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool -
Ocean View
US $2,944
/Night
7 Nights - $20,611
House
6 Bedrooms
5 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $2,929
/Night
7 Nights - $20,506
House
3 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $2,893
/Night
7 Nights - $20,249
House
6 Bedrooms
6 Bathrooms
12 Guests
5190 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $2,651
/Night
7 Nights - $18,557
House
10.0
(
26 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
4100 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $2,303
/Night
7 Nights - $16,120
House
10.0
(
9 Reviews
)
7 Bedrooms
4 Bathrooms
14 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $2,274
/Night
7 Nights - $15,918
House
9.6
(
19 Reviews
)
7 Bedrooms
4 Bathrooms
26 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $2,203
/Night
7 Nights - $15,421
See More Annapolis Luxury Vacation Rentals
Find More Annapolis Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Annapolis
Over 179+
Top-Rated Vacation Rentals with a Pool in or Near Annapolis
House
10.0
(
211 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $542
/Night
7 Nights - $3,795
House
10.0
(
141 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $662
/Night
7 Nights - $4,637
House
10.0
(
124 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2200 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $718
/Night
7 Nights - $5,027
New
Cabin
10.0
(
92 Reviews
)
2 Bedrooms
1 Bathroom
10 Guests
1250 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $596
/Night
7 Nights - $4,170
Apartment
10.0
(
84 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $515
/Night
7 Nights - $3,607
Cottage
10.0
(
55 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $950
/Night
7 Nights - $6,653
House
10.0
(
54 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2500 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $675
/Night
7 Nights - $4,724
House
10.0
(
34 Reviews
)
3 Bedrooms
4 Bathrooms
10 Guests
3200 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $1,576
/Night
7 Nights - $11,030
Pet-Friendly Vacation Rentals in Annapolis
Over 415+
Pet-Friendly Vacation Rentals in or Near Annapolis
House
10.0
(
207 Reviews
)
5 Bedrooms
3 Bathrooms
23 Guests
3690 ft²
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $717
/Night
7 Nights - $5,018
10.0
(
8 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
10763.91 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $991
/Night
7 Nights - $6,937
8.2
(
1006 Reviews
)
1 Bathroom
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $114
/Night
7 Nights - $796
House
9.8
(
59 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $765
/Night
7 Nights - $5,355
House
9.8
(
72 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $871
/Night
7 Nights - $6,097
Cottage
10.0
(
110 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
652 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $313
/Night
7 Nights - $2,189
House
10.0
(
74 Reviews
)
2 Bedrooms
3 Bathrooms
8 Guests
2400 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $616
/Night
7 Nights - $4,309
Cottage
10.0
(
69 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Spa
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $602
/Night
7 Nights - $4,217
See More Pet-Friendly Vacation Rentals in Annapolis on PetFriendly.io
Large Vacation Homes & Villas in Annapolis
Over 353+
Large Vacation Homes & Villas in or Near Annapolis
House
10.0
(
76 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
1800 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $1,260
/Night
7 Nights - $8,820
10.0
(
3 Reviews
)
6 Bedrooms
5 Bathrooms
18 Guests
5597.23 ft²
-
Spa
-
Fireplace/Heating
-
Pool
-
View
US $955
/Night
7 Nights - $6,682
House
10.0
(
8 Reviews
)
5 Bedrooms
2 Bathrooms
13 Guests
2400 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $910
/Night
7 Nights - $6,368
Cottage
10.0
(
226 Reviews
)
3 Bedrooms
2 Bathrooms
11 Guests
1850 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $488
/Night
7 Nights - $3,419
House
10.0
(
76 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $1,074
/Night
7 Nights - $7,521
House
10.0
(
47 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $623
/Night
7 Nights - $4,360
House
10.0
(
43 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
3415 ft²
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $926
/Night
7 Nights - $6,484
House
10.0
(
36 Reviews
)
6 Bedrooms
5 Bathrooms
14 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $1,180
/Night
7 Nights - $8,263
See More Family Vacation Rentals in Annapolis on FVR
Wheelchair Accessible Vacation Homes in Annapolis
Over 129+
Wheelchair Accessible Vacation Homes in or Near Annapolis
Condo
10.0
(
41 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
991 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $414
/Night
7 Nights - $2,897
10.0
(
1 Review
)
7 Bathrooms
393.65 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Breakfast
US $311
/Night
7 Nights - $2,179
Hotel
10.0
(
6 Reviews
)
1 Bathroom
-
Balcony/Terrace
-
Breakfast
-
Parking
-
Air Conditioner
US $310
/Night
7 Nights - $2,167
Condo
10.0
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
983 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $548
/Night
7 Nights - $3,838
House
10.0
(
1 Review
)
3 Bedrooms
4 Bathrooms
8 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $1,419
/Night
7 Nights - $9,933
House
9.0
(
8 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $1,460
/Night
7 Nights - $10,220
Condo
1 Bedroom
1 Bathroom
4 Guests
526 ft²
-
Private Pool
-
Oceanfront
-
Fireplace/Heating
-
Pool
US $624
/Night
7 Nights - $4,369
House
10.0
(
20 Reviews
)
6 Bedrooms
6 Bathrooms
14 Guests
8300 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $1,825
/Night
7 Nights - $12,772
Annapolis Vacation Rentals and Airbnb Places to Stay Under $200
Over 182+
Annapolis Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
9.6
(
91 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
485 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $155
/Night
7 Nights - $1,083
9.6
(
18 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
4305.56 ft²
-
Fireplace/Heating
-
Parking
-
Air Conditioner
-
Internet
US $120
/Night
7 Nights - $843
9.4
(
1005 Reviews
)
1 Bathroom
-
Breakfast
-
Kitchen
-
Parking
-
Air Conditioner
US $186
/Night
7 Nights - $1,302
New
House
2.0
(
1 Review
)
4 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Child Friendly
US $182
/Night
7 Nights - $1,275
New
House
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Child Friendly
US $190
/Night
7 Nights - $1,331
House
3 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $188
/Night
7 Nights - $1,316
New
Bed & Breakfast
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $177
/Night
7 Nights - $1,236
New
House
1 Bedroom
2 Bathrooms
2 Guests
750 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $144
/Night
7 Nights - $1,011
See More Annapolis Vacation Rental Deals
Instantly Bookable Vacation Homes in Annapolis
Over 699+
Instantly Bookable Vacation Homes in or Near Annapolis
House
10.0
(
226 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1295 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $536
/Night
7 Nights - $3,754
House
9.8
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $457
/Night
7 Nights - $3,196
House
10.0
(
210 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2335 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $922
/Night
7 Nights - $6,456
House
9.6
(
51 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $896
/Night
7 Nights - $6,272
House
10.0
(
38 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1188 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $345
/Night
7 Nights - $2,414
House
9.6
(
19 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
3000 ft²
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
-
View
US $730
/Night
7 Nights - $5,110
Cottage
10.0
(
174 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
950 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $352
/Night
7 Nights - $2,462
House
10.0
(
99 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $469
/Night
7 Nights - $3,284
About Annapolis Vacation Rentals
With more than 6 Annapolis vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Annapolis.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Annapolis, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Annapolis. Places to stay near Annapolis are 5185.77 ft² on average, with prices averaging US $916 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Annapolis with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Annapolis
| Type | Count |
|---|---|
| Villas | 6 |
Use these Quick Filters to Find a Vacation Rental in Annapolis
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Annapolis.
Weather in Annapolis
View the weather forecast for Annapolis before booking your Annapolis Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Annapolis, MD
Estiavillas offers a large selection of top attractions around Annapolis. Research things to do on your vacation before you visit Annapolis.
U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Bowie State University
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Annapolis Maritime Museum
Allen Pond Park
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club
Maryland World War II Memorial
William Paca House
The Kunta Kinte Alex Haley Memorial
Other Places to Stay Near Annapolis, MD
Northern Chesapeake Bay
5,277 Properties
Murray Hill
874 Properties
Spa Creek
873 Properties
Historic District
193 Properties
Selby-on-the-Bay
117 Properties
Cape Saint Claire
104 Properties
Parole
51 Properties
Kent Island
45 Properties
Stevensville
40 Properties
Bowie
35 Properties
Eastport
32 Properties
Edgewater
25 Properties
Complexes around Annapolis, MD
Annapolis Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Annapolis?
There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Annapolis:
- Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!
- USNA Home Downtown Annapolis
- 1879 Downtown Annapolis Home with Koi Ponds and Gardens
- 8 Bells Bungalow - Cozy, Stylish, Prime Location
- Luxurious Waterfront Kent Island Home 30 miles from Annapolis
- Exquisite 14,000 sq ft Waterfront Mansion with Pool
How many vacation rentals have private pools in Annapolis?
There are 64 vacation rentals with private pools near Annapolis. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Annapolis are best for families?
If you are looking for a family-friendly vacation home in Annapolis, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Annapolis:
How many vacation rentals are available in Annapolis?
Currently, the total number of properties listed in 2026 is over 6 in the Annapolis area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Annapolis.
