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 New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
19–26 Oct
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
6–13 Jul
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
14–21 Sep
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
20–27 Oct
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
5–12 Sep
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
8–15 Jan
Home in Fairfax
4.96 out of 5 average rating, 144 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
7–14 Dec
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
28 Sep – 5 Oct
Apartment rentals with a pool
Apartment in McLean
4.82 out of 5 average rating, 126 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
26 Mar – 2 Apr
Apartment in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
12–19 Jun
Apartment in Annapolis
4.97 out of 5 average rating, 68 reviewsSpring into Annapolis-very low cleaning fee
29 Oct – 5 Nov
Apartment in Annapolis
5.0 out of 5 average rating, 6 reviewsCharming Annapolis Waterfront Condo
30 Nov – 7 Dec
Apartment in Annapolis
4.94 out of 5 average rating, 35 reviewsCozy Annapolis Condo
30 Jun – 7 Jul
Apartment in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
19–26 May
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
25 May – 1 Jun
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
1.5K reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
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