Please note that most properties rent in 4 week increments rather than the calendar months. Your rental manager will provide the specific dates for your winter booking.

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Seaside at Anastasia E204 is a 3-bedroom, 2-bathroom second floor luxury condo within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses.  You are sure to have a great stay in this beach condo with all of the ... Read more »

26 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Beds: King, Queen, 2 Twins
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Island South 26 is a lovely 2-bedroom, 2-bathroom second floor walk-up unit, just steps to the private boardwalk and beautiful St. Augustine Beach. Island South Condominiums is the perfect vacation spot, close to restaurants, shopping and the Fishing Pier, and just a short drive to the downtown His... Read more »

22 people are interested in this property!

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  • Location: Ocean View
  • Property Type: Island South
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: Q,Q,SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

Available Jan-March for Snowbird Season! Call 904.471.7513 to Book Today!
Ocean Village Club Q19 is a corner unit 2 Bedroom, 2 Bathroom Condo located on the ground floor of a popular gated community. From this Oceanside unit you can walk right out to one of two pools and the boardwalk access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club gives ... Read more »

30 people are interested in this property!

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  • Location: Ocean Front/Dunes View
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, TT, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Enjoy all the Season has to Offer! 10% off select reservations Oct-Dec 2026.
  Ocean Village Club N21 is a 1 Bedroom, 1 Bathroom Condo located on the 2nd floor (walk up) of a popular gated community. Just a short walk across property to either of the two pools (1 heated) and access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club gives you access to... Read more »

30 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 4
  • Bedrooms: 1
  • Beds: Q, SS
  • Baths: 1
  • Pets: No
  • Parking Spots: 2

Enjoy a little downtime at Crescent Beach with this 2 bed/2 bath condo located on the ocean with views of both the Atlantic and the Intracoastal! Comfortable living spaces with a 42" flat screen TV/DVD/VCR, CD Player/Bose speakers, and a fully equipped kitchen await you when you return from the beac... Read more »

26 people are interested in this property!

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  • Location: Ocean Front
  • Property Type: Windjammer
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: King/2 Twins/SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

Available Jan-March for Snowbird Season! Call 904.471.7513 to Book Today!
For Jan-Mar 2026 availablity, please call the Ocean Village Club rental office!   Ocean Village Club P22 is an updated 2 Bedroom, 2 Bathroom Condo located on the 2nd floor (walk up) of a popular gated community. Just steps away from one of two pools and the boardwalk access to beautiful St. Aug... Read more »

36 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, TT, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Anastasia 412 is a 2-bedroom, 2-bathroom 4 th floor unit. Enjoy the white sand beaches of St. Augustine or walk the streetsof historic down town. This condo is in the perfect location for you vacationneeds. Features: 2 bedroom/2 bathroom Newly remodeled Open air Balcony Steps From the Oce... Read more »

22 people are interested in this property!

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  • Location: Ocean View
  • Property Type: Anastasia
  • Sleeps: 4
  • Bedrooms: 2
  • Beds: K, Q
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Tradewinds 53 is a bright and airy renovated third floor oceanview unit.  The private balcony is right off the living room and has a gorgeous view of the beach and community pool. This unit features: 2 bedroom, 2 bathroom condo (sleeps 6 guests) Oceanview balcony Updated kitchen with granite... Read more »

38 people are interested in this property!

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  • Location: Ocean View
  • Property Type: Tradewinds
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: King, Queen, Sleeper Sofa
  • Baths: 2
  • Pets: No

Available Jan-March for Snowbird Season! Call 904.471.7513 to Book Today!
Ocean Village Club P31 is an updated 2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Just steps from one of two pools and the boardwalk access to beautiful St. Augustine Beach!    Being a guest at Ocean Village Club gives you access to the private bo... Read more »

30 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, TT, TT, SS
  • Baths: 2
  • Pets: No

Enjoy all the Season has to Offer! 10% off select reservations Oct-Dec 2026.
- Ocean Village Club P28 is a corner unit 2 Bedroom, 2 Bathroom Condo located on the 2nd floor (walk up) of a popular gated community. Just steps away from one of two pools and the boardwalk access to beautiful St. Augustine Beach!  Being a guest at Ocean Village Club gives you access to the pr... Read more »

10 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: Q, TT, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Seaside at Anastasia G302 is a 3-bedroom, 2-bathroom top floor unit within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses.  You are sure to have a great stay in this beach condo with all of the nearby acti... Read more »

33 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Beds: K, Q, 2 Twins
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Anastasia 103 is a updated 2-bedroom, 2-bathroom ground floor unit within walking distance to the gorgeous beaches of St Augustine. Providing guests luxury finishes and close proximity to the beach this unit is sure to please.    Features: 2 Bedroom, 2 Bathroom Ground floor unit Enclosed ... Read more »

26 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Anastasia
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: King, Full, Sleeper sofa
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

This 2 bed/2 bath condo is located right on Crescent Beach where you can relax on your private balcony and enjoy some of the most beautiful sunrises you have ever seen! The condo is set up with balcony access from either the master bedroom or the living area. The living area is furnished with a 32" ... Read more »

33 people are interested in this property!

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  • Location: Ocean Front
  • Property Type: Windjammer
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: King, Queen, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

**January thru March Available**
This adorable 1BR/1BA ground floor condo is adjacent to the Pool with a Courtyard view. The Living Room offers a new Sleeper Sofa and a Flat Screen TV. Beach Chairs and Beach Towels are available for your Fun in the Sun. Creston House guests enjoy a large pool, private boardwalk to beautiful, whit... Read more »

17 people are interested in this property!

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  • Location: Courtyard Near Ocean
  • Property Type: Creston House
  • Sleeps: 4
  • Bedrooms: 1
  • Beds: K, SS
  • Baths: 1
  • Pets: No
  • Parking Spots: 1

Ocean Village Club K32 is a beautifully remodeled 2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Next to the heated (in Winter) pool and just a short walk across property to a 2nd pool and access to beautiful St. Augustine Beach!   Being a guest at ... Read more »

15 people are interested in this property!

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  • Location: Courtyard Near Ocean
  • Property Type: Ocean Village Club
  • Sleeps: 4
  • Bedrooms: 2
  • Beds: K, Q
  • Baths: 2
  • Pets: Yes

NEW TO PROGRAM!  Seaside at Anastasia G301 is a 3-bedroom, 2-bathroom top floor unit within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses.  You are sure to have a great stay in this beach condo with all of... Read more »

41 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Beds: K, Q, TT
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

Windjammer Condominium 407 - Your Perfect Beachside Retreat in St. Augustine, FL! Welcome to Windjammer Condominium 407, located in the heart of beautiful St. Augustine, Florida! This charming 2-bedroom, 2-bathroom vacation rental is the ideal spot for your next coastal getaway. Nestled at 7780 A... Read more »

13 people are interested in this property!

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  • Location: Ocean Front
  • Property Type: Windjammer
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, T, T, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

Seaside at Anastasia F101 is a 3-bedroom, 2-bathroom ground floor unit within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses. You are sure to have a great stay in this beach condo with all of the nearby ac... Read more »

21 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Enjoy all the Season has to Offer! 10% off select reservations Oct-Dec 2026.
Ocean Village Club A32 is a 1 Bedroom, 1 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Just a short walk across property to either of the two pools (1 heated) and access to beautiful St. Augustine Beach!   Being a guest at Ocean Village Club gives you access to... Read more »

22 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 4
  • Bedrooms: 1
  • Beds: K, SS
  • Baths: 1
  • Pets: No
  • Parking Spots: 2

Seaside at Anastasia E102 is a 3-bedroom, 2-bathroom ground floor unit within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses.  You are sure to have a great stay in this beach condo with all of the nearby ac... Read more »

27 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Beds: K, Q, TT
  • Baths: 2
  • Pets: No
  • Parking Spots: 1

Enjoy all the Season has to Offer! 10% off select reservations Oct-Dec 2026.
  Ocean Village Club O32 is an oceanview 2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Overlooking one of two pools and the boardwalk access to beautiful St. Augustine Beach!    Being a guest at Ocean Village Club gives you access to the private ... Read more »

21 people are interested in this property!

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  • Location: Ocean View/Pool View
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, TT, SS
  • Baths: 2
  • Pets: No

Check Out Our New Rates and Snowbird Availability!
Ocean Village Club J36 is a 2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. A remodeled unit with a touch of shabby chic makes this condo unique. Located next to the heated pool (in winter) and just a short walk on property to a second pool and access to... Read more »

36 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K, TT, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

St Augustine Beach & Tennis Resort 611 is a lovely 2 bedroom, 2.5 bath townhome located in a gated complex and is a short walk to the beautiful sugar sand St Augustine beaches. There is an outdoor heated pool and is close to restaurants, shopping, the St Augustine Lighthouse and Alligator Farm. It'... Read more »

12 people are interested in this property!

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  • Location: Courtyard Near Ocean
  • Property Type: St. Augustine Beach & Tennis Resort
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: Q, TT, SS
  • Baths: 2
  • Half: 1
  • Pets: Yes
  • Parking Spots: 1

**January thru March Available**
This 2BR/2BA Town Home condo has a spectacular view of the pool as well as the Ocean! It's a definite must-see. Newly furnished with a modern beachy touch, it's quite the conversation piece! The Living Room has a flat screen TV as does the Master Bedroom. The Guest Bedroom has a balcony to relax in... Read more »

18 people are interested in this property!

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  • Location: Ocean View
  • Property Type: Creston House
  • Sleeps: 4
  • Bedrooms: 2
  • Beds: Q,Q
  • Baths: 2
  • Pets: No

Available Jan-March for Snowbird Season! Call 904.471.7513 to Book Today!
Ocean Village Club B33 is a beachy 1 Bedroom, 1 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Just a short walk across property to either of the two pools (1 heated) and access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club gives you access... Read more »

14 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 3
  • Bedrooms: 1
  • Beds: Q, T
  • Baths: 1
  • Pets: No
  • Parking Spots: 2

Ocean Club I Unit 32 is a lovely 2 bedroom, 2 bathroom townhouse with a one-car garage that is just a short walk to the beach via Dondanville Rd. In addition to beautiful St Augustine Beach, you'll enjoy area restaurants, shopping and the historic downtown area. Features: 2 Bedroom, 2 Bathroom ... Read more »

16 people are interested in this property!

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  • Location: Courtyard Near Ocean
  • Property Type: Ocean Club I
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K,T,T,SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Ocean Village Club O36 is an oceanview 2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Overlooking one of two pools and the boardwalk access to beautiful St. Augustine Beach!    Being a guest at Ocean Village Club gives you access to the private boar... Read more »

20 people are interested in this property!

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  • Location: Ocean View
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: Q, TT, SS
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Ocean Village Club N34 is a 1 Bedroom, 1 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community. Just a short walk across property to either of the two pools (1 heated) and access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club gives you access to the p... Read more »

17 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 4
  • Bedrooms: 1
  • Beds: K, F
  • Baths: 1
  • Pets: Yes

Ocean Village Club B26 is a 1 Bedroom, 1 Bathroom Condo located on the 2nd floor (walk up) of a popular gated community. Just a short walk across property to either of the two pools (1 heated) and access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club gives you access to the... Read more »

7 people are interested in this property!

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  • Location: Near Ocean/Oceanside
  • Property Type: Ocean Village Club
  • Sleeps: 2
  • Bedrooms: 1
  • Baths: 1
  • Pets: No

**January thru March Available**
Newly Remodeled 1BR/1BA Ground floor unit that takes you right to the Pool from the patio with a Courtyard view! There's a Sleeper sofa in living room that overlooks the beautiful lawns. With this unit being one floor, there are no steps to climb.   A Washer and Dryer is right in the unit for your ... Read more »

30 people are interested in this property!

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  • Location: Poolside
  • Property Type: Creston House
  • Sleeps: 4
  • Bedrooms: 1
  • Beds: K, SS
  • Baths: 1
  • Pets: No
  • Parking Spots: 1

Seaside at Anastasia A206 is a newly renovated 3-bedroom, 2-bathroom second floor unit within walking distance to the gorgeous beaches of St. Augustine, the local pier, and several local restaurants, coffee shops, and small businesses.  You are sure to have a great stay in this beach condo with all... Read more »

27 people are interested in this property!

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  • Location: Lake Front, Near Ocean & Pool
  • Property Type: Seaside at Anastasia
  • Sleeps: 6
  • Bedrooms: 3
  • Beds: K, Q, 2 Twin
  • Baths: 2
  • Pets: No
  • Parking Spots: 2

Available Jan-March for Snowbird Season! Call 904.471.7513 to Book Today!
Ocean Village Club G32 is a  2 Bedroom, 2 Bathroom Condo located on the 3rd floor (walk up) of a popular gated community.Overlooking the heated (in Winter) pool and just a short walk across property to a 2nd pool and access to beautiful St. Augustine Beach! Being a guest at Ocean Village Club ... Read more »

6 people are interested in this property!

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  • Location: Pool/Court Yard View
  • Property Type: Ocean Village Club
  • Sleeps: 6
  • Bedrooms: 2
  • Beds: K,K,SS
  • Baths: 2
  • Pets: Yes