Search results; Over 1,000 places in Saint Leonard

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Guest favorite
Cottage in Saint Leonard
Block to Private Beach, Screened deck, Hot Tub
Free cancellation
Jun 22 – 27
R25,014 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 141 reviews
Superhost
Place to stay in Saint Leonard
Mermaids Paradise
2 beds
Jun 30 – Jul 5
R13,490 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 171 reviews
Guest favorite
Home in Saint Leonard
Cottage on the Bay
Free cancellation
Jun 23 – 28
R24,738 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 68 reviews
Home in Saint Leonard
Hickory House on the Chesapeake Bay!
2 beds
Jun 12 – 17
R16,878 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 51 reviews
Guest favorite
Home in Saint Leonard
Luxury 5BR: Beach, GameRm, Arcade, Theater
8 beds
Jun 22 – 27
R75,497 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 41 reviews
Guest favorite
Home in Saint Leonard
Cozy Beach House ~Chesapeake Bay Getaway
3 double beds
Jun 22 – 27
R21,282 ZAR for 5 nights
for 5 nights
4.84 out of 5 average rating, 64 reviews
Top guest favorite
Guesthouse in Saint Leonard
Studio on the Bay.
1 queen bed
Jun 29 – Jul 4
R19,175 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 111 reviews
Guest favorite
Home in Saint Leonard
Waterfront Home, Spectacular View & Private Beach!
3 beds
Jun 15 – 20
R47,620 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
Superhost
Guest suite in Saint Leonard
Shewell’s Basement Studio at Long Beach
1 king bed
Jun 15 – 20
R7,206 ZAR for 5 nights
for 5 nights
4.84 out of 5 average rating, 45 reviews
Top guest favorite
Home in Saint Leonard
J.K.'s by the Bay
4 beds
Jul 7 – 12
R25,706 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 39 reviews
Top guest favorite
Cottage in Lusby
Cozy Cottage close to Beaches & Solomon’s Island
Free cancellation
Jul 12 – 17
R21,050 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Saint Leonard
Block to beach! Relax, enjoy views & game room.
5 beds
Jun 10 – 15
R38,981 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 58 reviews
Guest favorite
Home in Saint Leonard
Escape to the Bay~Waterfront
6 beds
Jun 13 – 19
R58,087 ZAR for 6 nights
for 6 nights
4.91 out of 5 average rating, 32 reviews
Top guest favorite
Room in Leonardtown
Stay with KathleenRetired usn aviator,
Home away from home.
Jun 10 – 15
R4,741 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 36 reviews
Superhost
Home in Saint Leonard
Large Spacious 5 Bedroom 8 Bed House at Long Beach
8 beds
Jun 28 – Jul 3
R25,706 ZAR for 5 nights
for 5 nights
4.73 out of 5 average rating, 118 reviews
Guest favorite
Home in Saint Leonard
Large home w/ 6 bedrooms, 2 kitchens, and hot tub!
Free cancellation
Jul 21 – 26
R83,230 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 94 reviews
Apartment in Saint Leonard
The Loft at Flag Harbor
Free cancellation
Jun 15 – 20
R25,770 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cottage in Port Republic
Chesapeake Bay Cliffs Getaway
Free cancellation
Jun 20 – 25
R31,080 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 108 reviews