Vacation Rentals & House Rentals with Pool in Annapolis

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Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
Grill
Fireplace
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Games room
Clothes dryer
Table tennis
Pool or snooker table
Shared outdoor pool (unheated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Fax machine
Swing set or jungle gym
Video player
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Boat available
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Waterfront
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront

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17 apartments in Annapolis with pools

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Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

2 bedrooms
1 bathroom

sleeps 5

Match: Swimming pool

All filters match

Price per night from

$445

Luxury Waterfront home with private pier and guest house

Annapolis house

5 bedrooms
4 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$907

Free Parking with private fenced-in backyard with pool table at Weekender

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$292

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

2 bedrooms
2 bathrooms

sleeps 7

Match: Swimming pool

All filters match

Price per night from

$401

Great rentals within 20 miles that match your search

Waterfront Getaway - View of bay from your bed

Romancoke studio

Studio
1 bathroom

sleeps 2

Match: Swimming pool

All filters match

Price per night from

$230

The Annapolis General House

Parole house

4 bedrooms
4 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$690

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$716

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms
5 bathrooms

sleeps 10

Match: Swimming pool

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Price per night from

$1,117

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms
2 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$1,947

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms
3 bathrooms

sleeps 10

Match: Swimming pool

All filters match

Price per night from

$1,947

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$916

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$1,890

Cozy Cool Spring waterfront apartment with pier mins to Annapolis

Arnold apartment

1 bedroom
1 bathroom

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$177

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

4 bedrooms
4 bathrooms

sleeps 10

Match: Swimming pool

All filters match

Price per night from

$725

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

3 bedrooms
3 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$321

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

5 bedrooms
4 bathrooms

sleeps 14

Match: Swimming pool

All filters match

Price per night from

$727

Stay poolside for 2024 Commissioning Week! Pier & parking mins to USNA

Arnold house

4 bedrooms
3 bathrooms

sleeps 10

Match: Swimming pool

All filters match

Price per night from

$382

Also consider

Ocean City 148 properties
Baltimore 70 properties
Montgomery County 47 properties
North East 46 properties
National Harbor 13 properties
Talbot County 12 properties
Kent Island 11 properties
Calvert County 10 properties
Ocean Pines 10 properties
Glen Burnie 9 properties
Edgewater 9 properties
Oxon Hill 8 properties
Rosedale 7 properties
Mount Rainier 7 properties
Severna Park 7 properties
Suitland 5 properties
Marion Station 5 properties
Parkville 5 properties
Chillum 5 properties
Hampden 5 properties
Garrett County 5 properties
Fort Washington 5 properties
South Carolina 4,916 properties
Texas 4,474 properties
Pennsylvania 931 properties
Idaho 727 properties
Alaska 327 properties
Delaware 304 properties
Indiana 261 properties
Connecticut 154 properties
Mississippi 126 properties
North Dakota 49 properties

Annapolis Rentals with Pools

Per night

17 apartments in Annapolis with pools

Waterfront Condo Amazing Views with Resort Amenities

Luxury Waterfront home with private pier and guest house

Free Parking with private fenced-in backyard with pool table at Weekender

Walk to Main Street from Waterfront Condo with pool and parking

Waterfront Getaway - View of bay from your bed

The Annapolis General House

St. Michael's Premier in Town Summer Cottage now with private pool!

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Annapolis Area Shagrila Resort

Ship's Cove Inn and Resort in St. Michaels, MD

Cozy Cool Spring waterfront apartment with pier mins to Annapolis

Waterfront pier, putting green just minutes from downtown Annapolis

Pool and Bay Views on wrap around deck in Kent Island

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Stay poolside for 2024 Commissioning Week! Pier & parking mins to USNA

Viewing 17 of 17
rentals in Annapolis

Also consider

Annapolis Rentals with Pools

Per night

17 apartments in Annapolis with pools

Viewing 17 of 17rentals in Annapolis

Also consider

Viewing 17 of 17
rentals in Annapolis