Vacation 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.
Vacation 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
Oct 21 – 28
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 7 – 14
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 15 – 22
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Mar 28 – Apr 4
Home in Fairfax
4.96 out of 5 average rating, 144 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Jan 10 – 17
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jan 8 – 15
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Apr 4 – 11
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jan 3 – 10
Condo rentals with a pool
Condo in McLean
4.82 out of 5 average rating, 126 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Jul 28 – Aug 4
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 13 – 20
Condo in Annapolis
4.97 out of 5 average rating, 68 reviewsSpring into Annapolis-very low cleaning fee
Mar 3 – 10
Condo in Annapolis
5.0 out of 5 average rating, 6 reviewsCharming Annapolis Waterfront Condo
Sep 16 – 23
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Jan 9 – 16
Condo in Annapolis
4.94 out of 5 average rating, 35 reviewsCozy Annapolis Condo
Mar 22 – 29
Condo in Montgomery Village
4.76 out of 5 average rating, 33 reviewsHOME away HOME
May 6 – 13
Condo in Alexandria
5.0 out of 5 average rating, 6 reviewsQuiet Condo Near Alexandria ~ Ideal for long stays
May 25 – Jun 1
Quick stats about vacation 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
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