Holiday rentals with a pool in Baltimore

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Baltimore

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Guest favourite

Guest house in Annapolis

5.0 out of 5 average rating, 138 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

25 Jun – 2 Jul

€ 296 per night
Guest favourite

Guest suite in Adelphi

4.85 out of 5 average rating, 202 reviews

Cozy Suite with Hot Tub and Pool

Our cozy 3 room in-law suite is situated on 3 private acres with pool, hot tub, extensive gardens, hiking trails, parking, cable and wireless internet. Convenient to University of MD, Washington DC, and surrounding areas. Kids and pets welcome. Local attractions include the National Archives, Smithsonian Museum, Folger Shakespeare Library, Library of Congress, Lincoln Memorial, White House, Washington Memorial, National Mall, Arlington Cemetery, Spy Museum, Holocaust Museum, Annapolis etc.

11–18 Jan

€ 181 per night
Guest favourite

Guest house in Owings Mills

4.96 out of 5 average rating, 111 reviews

Shamrock cabin with hot tub, large yard

Please no cats! We are allergic. Backyard tiny house/guest house fits 2 adults comfortably. Equipped with small kitchenette, queen bed, and private bathroom. Kitchenette equipped with mini fridge, toaster oven, microwave, Keurig coffee machine, and silverware/dishware. Snacks/breakfast items and assorted k-cups provided. Dog friendly with spacious enclosed back yard containing private hot tub, small above ground pool, propane grill, fire pit, and badminton net. Includes Wi-Fi & TV with roku.

3–10 Apr

€ 99 per night

Popular amenities for Baltimore rentals with a pool

House rentals with a pool

Guest favourite

Home in Perry Hall

4.98 out of 5 average rating, 41 reviews

Gunpowder Retreat

3–10 Feb

€ 373 per night
Guest favourite

Home in Jessup

5.0 out of 5 average rating, 24 reviews

Family & Dog Friendly | Pool | Prime Location

3–10 Oct

€ 343 per night
Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

1–8 May

€ 109 per night
Superhost

Home in Sykesville

4.92 out of 5 average rating, 60 reviews

Casa Blanca, where Luxury meets Serenity

1–8 Jan

€ 829 per night
Guest favourite

Home in Gaithersburg

5.0 out of 5 average rating, 9 reviews

Townhouse in Gaithersburg

20–27 Jun

€ 159 per night
Superhost

Home in Milford Mill

5.0 out of 5 average rating, 4 reviews

Hidden Gem w/ Pool

6–13 Aug

€ 1,112 per night
Guest favourite

Home in Stevensville

4.98 out of 5 average rating, 61 reviews

Beautiful Kent Island Getaway with Pool

12–19 Nov

€ 758 per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 15 reviews

Impressive Waterfront Home - Pool, Pier, & Sunsets

9–16 Apr

€ 1,155 per night
Guest favourite

Home in Stevensville

5.0 out of 5 average rating, 99 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

15–22 Aug

€ 972 per night
Guest favourite

Home in Edgewater

4.97 out of 5 average rating, 29 reviews

Waterfront | Pool | Hot tub | Beach Access

17–24 Apr

€ 428 per night
Guest favourite

Home in Annapolis

4.96 out of 5 average rating, 25 reviews

Waterfront Oasis with Private Pool, Hot Tub, Piers

7–14 Dec

€ 1,188 per night
Guest favourite

Home in Annapolis

4.94 out of 5 average rating, 62 reviews

South River Retreat, Annapolis MD

27 Oct – 3 Nov

€ 947 per night

Apartment rentals with a pool

Superhost

Apartment in Baltimore

5.0 out of 5 average rating, 5 reviews

Architect's Home - Historic w/ Contemporary Design

31 Jan – 7 Feb

€ 132 per night
Guest favourite

Apartment in Bethesda

4.93 out of 5 average rating, 28 reviews

Vibrant Apartment in Bethesda.

4–11 Aug

€ 189 per night
Guest favourite

Apartment in Annapolis

4.97 out of 5 average rating, 68 reviews

Spring into Annapolis-perfect location

31 Jul – 7 Aug

€ 208 per night
Guest favourite

Apartment in Arlington

4.94 out of 5 average rating, 87 reviews

Lovely 1-Bedroom Condo with Pool and City View

19–26 Feb

€ 207 per night
Guest favourite

Apartment in Washington

4.88 out of 5 average rating, 42 reviews

Free Parking, Balcony, Elevator, and Big Recliners

1–8 May

€ 183 per night
Guest favourite

Apartment in Annapolis

4.94 out of 5 average rating, 34 reviews

Cozy Annapolis Condo

23–30 Sep

€ 330 per night
Guest favourite

Apartment in Washington

4.97 out of 5 average rating, 32 reviews

Chic 2 bed/2 bath Condo steps from White House

4–11 Oct

€ 445 per night
Superhost

Apartment in Annapolis

4.5 out of 5 average rating, 4 reviews

Walk to Main St Waterfront condo, pool, parking

15–22 Feb

€ 478 per night
Superhost

Apartment in Annapolis

New place to stay

Charming Annapolis Waterfront Condo

6–13 Dec

€ 339 per night
Superhost

Apartment in Silver Spring

Beautiful Entire Condo near downtown Silver Spring

21–28 Oct

€ 181 per night
Guest favourite

Apartment in Annapolis

4.96 out of 5 average rating, 208 reviews

Annapolis Waterfront Condo - Unit #: A-203

15–22 Dec

€ 175 per night

Apartment in Washington

4.85 out of 5 average rating, 242 reviews

NEW Large Luxe Condo Rooftop Pool Prime Location

8–15 Sep

€ 285 per night

Quick stats about holiday rentals with a pool in Baltimore

Total rentals

100 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1.3K reviews

Nightly prices starting at

€ 18 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Baltimore
  5. Rentals with pools