Holiday rentals with a pool in Annapolis
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Annapolis
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis rentals with a pool
House rentals with a pool
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
27 Jan – 3 Feb
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
28 Oct – 4 Nov
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
19–26 Jun
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
8–15 Jan
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
3–10 Jan
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
31 Oct – 7 Nov
Home in Annapolis
4.94 out of 5 average rating, 62 reviewsSouth River Retreat, Annapolis MD
14–21 Mar
Apartment rentals with a pool
Apartment in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
13–20 Jun
Apartment in Annapolis
4.97 out of 5 average rating, 68 reviewsSpring into Annapolis-very low cleaning fee
3–10 Mar
Apartment in Annapolis
5.0 out of 5 average rating, 7 reviewsCharming Annapolis Waterfront Condo
12–19 Dec
Apartment in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
13–20 Jan
Apartment in Annapolis
4.94 out of 5 average rating, 35 reviewsCozy Annapolis Condo
7–14 Dec
Apartment in Montgomery Village
4.76 out of 5 average rating, 33 reviewsHOME away HOME
6–13 May
Apartment in Alexandria
5.0 out of 5 average rating, 6 reviewsQuiet Condo Near Alexandria ~ Ideal for long stays
Apartment in Annapolis
4.5 out of 5 average rating, 4 reviewsWalk to Main St Waterfront condo, pool, parking
17–24 Apr
Quick stats about holiday rentals with a pool in Annapolis
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5T reviews
Nightly prices starting at
₹3,336 before taxes and fees
Destinations to explore
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