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Holiday Rentals with Pools in St. Augustine

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    Travellers to St. Augustine are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    979 Matching Rentals in St. AugustineView all 1,623 rentals
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    Beautifully Renovated 3 Bedroom Oceanview Condo1 / 22
    (18)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    OVC Ground floor. April 15-22 & May Days Open.Short walk to Beach!1 / 23
    (89)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Oceanfront Home- Casa Del Sol- Live the LIFE!  4 decks, beach gear, grill...1 / 29
    (53)Excellent
    4 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Colony Reef 1408, Recently Remodeled, 3BR/2BA Ocean view Condo w/Private WiFi1 / 25
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Pool, Hot Tub, Golf Cart, Outdoor TV, Pet friendly 72 in TV w/ full cable pkg1 / 47
    (27)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32084
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    GREAT SPECIAL! 3/25-4/1 ONLY $1500 ALL IN! 6 BR, HEATED POOL, ELEVATOR, VIEWS!1 / 32
    (123)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Last Wk April or May $750 + fees Clean, Comfy, Views, Convenient, Reviews!1 / 50
    (95)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Two Bedroom Ocean Front Beach Condo With Ocean Views1 / 24
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32084
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    St Augustine, Remodeled Oceanfront 3-Bedroom with Beautiful Views.  Great Deal1 / 34
    (31)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Book now for Winter!1 / 22
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Stunning Large 3 Bedroom Direct Ocean Front Condo. Heated pool/Spa.1 / 45
    (30)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Half off 2nd week if you book this fall!  It's a great time to be here!1 / 34
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    BOOK NOW!!! DISCOUNTED WINTER MONTHLY RATES!1 / 33
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Ocean Gallery -The Gold Standard For Beach Rentals1 / 23
    (43)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beso del Sol Beach Condo - Rated 5 Stars By our Wonderful Guests!1 / 32
    (58)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Love Shack Oceanfront 5 Master King Suites Pool Home Sleeps 141 / 38
    (59)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Full OCean FRONT 3rd FL  Barefoot Trace, Call/Speak w/Owner1 / 39
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    What's your pleasure? Stroll the beach, a game of tennis, or lounge by the pool?1 / 40
    (22)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    The Sandy Anchor - Best Location On St. Augustine Beach1 / 33
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    OCEAN GALLERY OCEANFRONT compare my rates!! CLEAN and UPDATED!1 / 33
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    St Augustine Crescent Beach Beachfront Ocean View Heated Pool RELAX1 / 26
    (77)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Panoramic Oceanview Home With Private Pool And Only 100 Yards To The Beach!!1 / 24
    (54)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Sundance LUXURY beach HOUSE on ocean. 68-5 star reviews. NO hurricane damage1 / 24
    (61)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32084
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Pier Point South Unit 26... Sun, Surf, And America's Oldest City Await You1 / 42
    (37)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    CLOSEST TO BEACH! Oceanfront, Ground Floor, King Bed, Kids Backyard, 2 Pools1 / 47
    (59)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beach Style! Steps from the Beach!Pools,Tennis,2BR/2BA Villa,Clean,WIFI,Reviews1 / 28
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Private Pool Beach House With No Extra Hidden Fees and no Cleaning Fee1 / 50
    (40)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Just steps from beach access with amazing ocean views! New kitchen remodel!1 / 50
    (19)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
    AFFORDABLE AND OCEAN VIEW!1 / 50
    (98)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Dir Ocean Front 2 BR/2 BA Condo1 / 24
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    314 Pacifica Vista Way Ocean Gallery Condo 3rd Floor  Southern Exposure1 / 22
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Steps to the non-driving section of the beach!1 / 23
    (37)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beach Bliss.OVC. Short Stroll to Beach. Near Pool. May Days Summer Weeks Avail.1 / 24
    (138)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Private 3 Bedroom Pool Home - ONLY 300 Yards To The Beach1 / 24
    (42)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Gorgeous Oceanfront 3 Bedroom Condo with pool!1 / 39
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Conquistador Wetlands, Panorama Views, Eagles, Herons, Ibises;.....peaceful1 / 26
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Augustine, Florida 32086
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Private Ocean View Pool Home with  no busy streets to cross; on Quiet Street.1 / 24
    (31)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Jan available contact for monthly rate Heated Pool Gated Community1 / 44
    (60)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Augustine Beach, St. Augustine 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Like Being in Oceanfront Heaven, Renovated, Dedicated High Speed Internet1 / 24
    (52)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Oceanfront Condo With Spectacular Ocean  Views1 / 30
    (41)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Brand New Home steps from the beach1 / 25
    (58)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    St. Augustine, Florida 32084
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    ONLY 2 PEAK WEEKS LEFT!  NEW DIRECT OCEANFRONT, 5 KING SUITES, POOL ROOF DECK!1 / 38
    (39)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    St. Augustine, Florida 32080
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
    Beautiful, FULL OCEANFRONT Condo! Barefoot Trace, St. Augustine, FL.1 / 30
    (28)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Comfy - family friendly - well equipped ... read our reviews !!!1 / 26
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Augustine, Florida 32080
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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