50 Best St. Augustine Beach rentals on Holiday Lettings - Vacation rentals

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77 properties
Vilano Beach
8 properties

St. Augustine

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284 Vacation rentals

20

Vilano Beach Vacation home rental

St. Augustine / Vilano Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
Just steps from the ocean with beautiful oceans views , breathtaking sunrises and sunsets sits the Mermaid's Beach House. This charming A frame beach cottage has all of the amenities needed, just show up with flip flops and a bathing suit and enjoy. Lots of parking , wi …see more

from $210 / night

$1200 - $2600 / week

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avg. 1 hour 59 minutes

from $210 / night

30

Vacation home in St. Augustine

Florida / St. Augustine

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
This well appointed home will provide comfort for multiple families with its two kitchens, five bedrooms and three full baths. The moment you drive up to Bella Vita you realize the hard work, compassion and attention to detail that was put into the remodeling of this l …see more

from $174 / night

$1170 / week

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avg. 3 hours 55 minutes

from $174 / night

37

Vacation apartment with shared pool in St. Augustine

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy this beautifully decorated 2 bedroom, 2 baths 3rd floor condo located in St. Augustine Ocean and Racquet. Only a short walk to the beach with a large, relaxing outdoor Jacuzzi. You get the amenities of the resort, including two pools, tennis courts, and fishing po …see more

from $125 / night

$595 - $795 / week

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avg. 2 hours 27 minutes

from $125 / night

(15) Very Good 

Certificate of Excellence

21

Vacation condo with shared pool in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Enjoy the pleasures of this luxurious condo nestled on Antastia Island near the old world charm and splendor located at the St. Augustine Ocean and Racquet Resort. Antastia Island has miles of beaches for you to enjoy. This adorable, freshly painted villa has a l …see more

Certificate of Excellence

from $95 / night

$575 - $800 / week

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from $95 / night

(2) Excellent 

33

Vacation apartment with shared pool in St. Augustine

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
"Sand in my Shoes" is a newly furnished Townhouse Condo, beautifully decorated 2 bedroom 2 ½ bath townhouse; Sleeps 6. Master suite with king size bed, walk-in shower, walk-in closet, with enclosed lanai upstairs with view of lagoon. Sliding doors open to the lanai to …see more

from $130 / night

$815 - $1199 / week

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from $130 / night

(2) Excellent 

24

Saint Augustine Beach Vacation apartment rental

St. Augustine / Saint Augustine Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
T'his gorgeous ground floor one bedroom, one bath condo has recently been painted and redecorated, and overlooks the pool and courtyard. New Glenwood Coastal Cypress flooring installed in November 2014. New living room furniture in Nov. 2014. This condo has plenty of ro …see more

from $79 / night

$550 - $1395 / week

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avg. 1 hour 32 minutes

from $79 / night

35

Apartment rental in St. Augustine with shared pool

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Come and enjoy the beach in this affordable condo that sleeps six comfortably. Beautifully decorated ground floor condo with patio. It has tile floors and carpeting in the bedrooms. Just a short walk to the beach and you will see why this unit will begin booking up fa …see more

from $100 / night

$495 - $795 / week

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avg. 2 hours 27 minutes

from $100 / night

(3) Excellent 

38

Vacation apartment with shared pool in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
With one of the best views at Ocean Village Club you have a perfect view of the beach side pool and ocean view all in one. Ocean Village Club is a family-friendly resort with all the amenities you could ask for. From the moment you enter our beautifully decorated condo …see more

from $150 / night

$695 - $1295 / week

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avg. 2 hours 27 minutes

from $150 / night

(8) Excellent 

17

Vacation apartment with shared pool in St. Augustine

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Total renovation with all white kitchen, granite, stainless steel appliances, white tile floors, beautifully decorated with original art and shabby chic beach look. Fluffy white towels, 42/32" flat screens, Wifi, HDTV, DVR and free long distance. We keep two beach bikes …see more

from $129 / night

$650 - $895 / week

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avg. 2 hours 46 minutes

from $129 / night

36

St. Augustine Vacation apartment rental

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
With only 48 units, Spanish Trace is one of the most sought after vacation experiences. Our unit at Spanish Trace sleeps a maximum of six and is one of the most economical getaway. Newly remodeled kitchen and first floor bathroom! Built on the shores of St. Augustine …see more

from $175 / night

$895 - $1050 / week

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avg. 2 hours 27 minutes

from $175 / night

(2) Excellent 

34

Apartment rental in St. Augustine with shared pool

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
First time this condo has ever been on a rental program. Be one of the first to stay in this beautifully decorated ground floor condo that sleeps six. This condo was renovated just two years ago. It has tile floors and carpeting in the bedrooms. Just a short walk to …see more

from $100 / night

$495 - $795 / week

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avg. 2 hours 27 minutes

from $100 / night

(2) Very Good 

20

Vacation apartment in St. Augustine

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
St. Augustine Beach/Crescent Beach all-Oceanfront condo complex with beautiful white sandy beaches framed by tall sea oats and sand dunes; yet only 15 minutes from historic downtown St. Augustine; our nation's oldest city! Four Winds Condominiums offers two heated pool …see more

from $150 / night

$775 - $975 / week

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avg. 2 hours 57 minutes

from $150 / night

23

Vacation home rental

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Take your next vacation in beautiful St. Augustine, Florida! Sea Haven Resort- 113 is a 2 bedroom, 2.5 bath condo ocean front  with the best ocean views. At 1280 square feet, this condo can comfortably sleep up to 6 people. Sea Haven Resort- 113 is located in St. August …see more

from $142 / night

$900 - $1300 / week

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from $142 / night

(3) Excellent 

37

Vacation apartment with shared pool in St. Augustine

Florida / St. Augustine

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in an oceanfront resort with two swimming pools (one heated), tennis courts, fitness center, shuffleboard, and so much more. The condo is conveniently located close to historic downtown St. Augustine. It's the perfect resort to start enjoying your vacation, anyt …see more

from $110 / night

$495 - $795 / week

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avg. 2 hours 27 minutes

from $110 / night

24

St. Augustine Vacation apartment rental

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous 1st floor poolside unit located at Sea Place. This 2 bedroom 2 bath condo has plenty to offer for guests looking to escape to the beach. Stack-able washer/dryer, large kitchen area with all appliances, queen size bed in master and two twin size beds in the sec …see more

from $125 / night

$750 - $1050 / week

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avg. 2 hours 27 minutes

from $125 / night

24

Vacation cottage rental

St. Augustine / Saint Augustine Beach

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Make plans to stay at this quaint 5-bedroom, 2-bathroom St. Augustine Beach vacation rental cottage for your next trip to the Sunshine State! Offering sleeping space for 12 guests, top notch amenities and an unbeatable oceanside location, ‘Salty Dog” leaves little to th …see more

from $215 / night

$1290 - $2550 / week

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from $215 / night

26

Vacation home in St. Augustine

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
WEEKENDS ARE 3 NIGHT STAY MINIMUM, when including a Friday or Saturday night stay. Week days, Mon - Thurs 2 night minimum stay. Also for last minute travel, if my calendar is open, 1 or two nights may be possible. Please contact with any questions. Happy to help :o)** …see more

from $155 / night

$1085 / week

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avg. 29 minutes

from $155 / night

35

Vacation apartment with shared pool in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy this beautifully decorated 2 bedroom, 2 baths 2nd floor condo located in St. Augustine Ocean and Racquet. Only a short walk to the beach with a large, relaxing outdoor Jacuzzi. You get the amenities of the resort, including two pools, tennis courts, and fishing po …see more

from $125 / night

$595 - $900 / week

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avg. 2 hours 27 minutes

from $125 / night

(4) Excellent 

12

Apartment rental in St. Augustine with shared pool

Florida / St. Augustine

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Great beach shabby chic decorating with HDTV, wifi, washer/dryer, flat screen, two rusted beach bikes for cruising the beach and town and beach toys all at an unbeatable price per week. You can't match great condo, great Club with a great price. Take some time and look …see more

from $99 / night

$450 - $695 / week

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avg. 2 hours 46 minutes

from $99 / night

(12) Very Good 

52

Vacation apartment with indoor pool, tennis court in St. Augustine

Florida / St. Augustine

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Description, Amenities and Location Description in English, Spanish, and French. Relax and feel miles away from the ordinary in this open space condo, featuring contemporary and coastal décor. This condo was newly renovated by its incoming owner in April 2014. This …see more

from $200 / night

$1381 - $1701 / week

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from $200 / night

24

Vacation home in St. Augustine

Florida / St. Augustine

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Fond memories, pristine shorelines and sparkling ocean waters await you at this pleasant 2-bedroom, 2-bath St. Augustine vacation rental house, which sleeps 7! With an ideal location merely blocks from beautiful beaches, lively entertainment and incredible options for o …see more

from $150 / night

$900 - $1295 / week

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from $150 / night

39

Vacation apartment in St. Augustine

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
What better way to experience local living than in our new Seaside Villas of Anastasia Island Condo. Located on the famous St. Augustine Beach corridor, this very comfortable get-away is less than 2-3 city blocks from the beach, local shops and restaurants. It is a ne …see more

from $110 / night

$595 - $895 / week

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avg. 2 hours 27 minutes

from $110 / night

(6) Excellent 

Certificate of Excellence

76

Saint Augustine Beach Vacation home rental

St. Augustine / Saint Augustine Beach

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
RECENT UPDATES: No damage from hurricane Mathew; 6.2 ft. J C surfboard for intermediate surfers, and the 8 ft. soft top surfboard Vitamix high speed $300+ blender New soft memory foam mattress toppers SUSTAINABLE HOUSE FEATURES: 3 solar systems: 17 panel Solar PV syst …see more

Certificate of Excellence

from $259 / night

$1595 - $3619 / week

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from $259 / night

24

Vacation home in Vilano Beach

St. Augustine / Vilano Beach

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
When looking for an Oceanfront Beach House Vacation Rental look no further. Octagon Blue, two different sized octagons connected to become one beautiful ocean front home. The entire East side of the home includes floor to ceiling windows facing the ocean. Our guests lov …see more

from $299 / night

$2099 - $2599 / week

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from $299 / night

17

Vacation home in St. Augustine

Florida / St. Augustine

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Walk out onto your choice of FOUR balconies to enjoy the spectacular view of the Atlantic. This beautiful ocean front home will take your breath away. Its three bedrooms and two bathrooms have all the luxuries of home. You will be minutes from downtown St Augustine' …see more

from $487 / night

$2185 / week

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from $487 / night

(1) Excellent 

24

St. Augustine Vacation apartment rental

Florida / St. Augustine

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Get away to the Sunshine State when you book this recently updated 3-bedroom, 2-bathroom St. Augustine Beach vacation rental condo. This charming unit, across the street from St. Augustine Beach, is ideally located near endless area attractions on Anastasia Island, offe …see more

from $155 / night

$1085 - $1435 / week

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from $155 / night

37

Vacation apartment in St. Augustine

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy our island-themed condo on the ground floor of the fun, family-oriented beach side Ocean Village Club complex. With space for the family, an enviable location, all the amenities of resort living, included wireless high speed Internet, and free unlimited long dista …see more

from $110 / night

$495 - $795 / week

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avg. 2 hours 27 minutes

from $110 / night

24

St. Augustine Vacation apartment rental

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Experience all that St. Augustine has to offer when you book this 2-bedroom, 2-bathroom apartment that comfortably sleeps 6. Ideally located in the heart of historic St. Augustine, above Preserved Restaurant, this newly renovated unit is the perfect home-base for a fami …see more

from $150 / night

$900 - $1590 / week

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from $150 / night

36

Apartment rental in St. Augustine with shared pool

Florida / St. Augustine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
****5 Night Minimum Stay Required**** Ocean Front Complex - New to Rental Market Get an authentic taste of beach living at its finest by escaping to St. Augustine Beach and Tennis 405, a wonderful St. Augustine Beach vacation rental condo! Ideally situated in a prist …see more

from $150 / night

$795 - $1195 / week

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avg. 2 hours 27 minutes

from $150 / night

(2) Excellent 

16

Vacation townhouse rental

St. Augustine / Saint Augustine Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Pet friendly
My place is a 5 minute walk to the beach (220 strides), restaurants and dining, great views, family-friendly activities, and art and culture. My place is good for couples, solo adventurers, and business travelers. There is a desk and a printer if you must work. This is …see more

from $119 / night

$833 / week

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avg. 2 hours 18 minutes

from $119 / night

(2) Excellent 

31

Apartment rental in Saint Augustine Beach with indoor pool

St. Augustine / Saint Augustine Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Get an authentic taste of beach living at its finest by escaping to ‘Sandy Feet,’ a wonderful St. Augustine Beach vacation rental condo! Ideally situated in a pristine oceanfront complex mere steps away from the sand and surf, ‘Sandy Feet’ ensures a seaside getaway you …see more

from $149 / night

$903 - $1480 / week

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from $149 / night

(8) Very Good 

31

Vacation cottage in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.06 mi
  • Child friendly
Our Beach Cottage is just steps away from one of the world's finest beaches... single story living, with 2 bedrooms: 1 with queen bed, 1 with 2 twin beds, comfortable open dining/living area with queen sofa bed, and two full bathrooms. The spacious fully equipped kitche …see more

from $249 / night

$1300 - $1720 / week

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from $249 / night

(2) Very Good 

28

Home accommodation in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Child friendly
Our Oceanside Beach House is just steps away from one of the world's finest beaches and features a Great Room with Fireplace, Full Kitchen, 2 Bedrooms, 2-1/2 baths, and Deck. You'll feel at home as soon as you walk in the door of Our Beach House. A dramatic (and romanti …see more

from $239 / night

$1673 / week

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from $239 / night

18

Vacation home in St. Augustine

Florida / St. Augustine

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
After recently spending some time in St. Augustine, our family fell in love with the city and wanted our own piece of this historical gem. While we’d love to enjoy our charming cottage year round, “real life” calls in another state and we’ve decided to share it with ot …see more

from $200 / night

$1200 / week

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Responds fast!
avg. 51 minutes

from $200 / night

(1) Excellent 

22

St. Augustine Vacation apartment rental

Florida / St. Augustine

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Relax and enjoy our newly refurbished designer decorated 2 bedroom 2 bath oceanside condo. Peek at the ocean thru the living room window. Completely repainted and refreshed. There is a comfy queen bed in master with new mattress set and bedding. The guest room includes …see more

from $120 / night

$600 - $1000 / week

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avg. 2 hours 39 minutes

from $120 / night

34

Vacation home in Saint Augustine Beach

St. Augustine / Saint Augustine Beach

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
**Teeming Vacation Rentals present Cranberry Cottage in St. Augustine Beach** Cranberry Cottage is teeming with personality and great location. This cozy home offers you and your family the perfect vacation spot and is located just 100 steps from one of the most pristi …see more

from $122 / night

$851 - $2063 / week

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avg. 3 hours 44 minutes

from $122 / night

(1) Very Good 

32

St. Augustine Vacation home rental

Florida / St. Augustine

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning pool is only the beginning when you choose to stay at Atlantic Oasis. It is located less than blocks away from the beach. Atlantic Oasis makes you feel delightfully secluded from the bustle of a busy beach town. Sit at the pool deck with a cool drink, or …see more

from $300 / night

$1395 - $2495 / week

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avg. 2 hours 27 minutes

from $300 / night

(3) Very Good 

43

Saint Augustine Beach Vacation condo rental

St. Augustine / Saint Augustine Beach

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
Beautiful 2bd/2bth St.Augustine beach condominium located on the 2nd floor in prestigious Ocean Gallery resort with a breathtaking southern exposure view of the Ocean. Easy access to the pool, hot tub, and steps away from the beach, shopping, and much more. When you wa …see more

from $200 / night

$1600 - $2520 / week

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from $200 / night

21

Vacation home rental

St. Augustine / Saint Augustine Beach

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Barefootin' Beach Duplex is only 45 barefoot steps to the dune (only 3 houses away)! You can see the ocean from your top floor decks and bedrooms,and then head off to the beach, or just swim in the beautiful heated pool in your backyard and have cocktails on the oceanv …see more

from $235 / night

$1870 - $2000 / week

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from $235 / night

23

Condo rental in Saint Augustine Beach with shared pool

St. Augustine / Saint Augustine Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in tropically landscaped gardens on miles of white sand beach only fifteen minutes from historic St. Augustine, this ground floor unit has a sunny, open floor plan that features 2 bedrooms with queen sized beds, two baths with showers, a large Jacuzzi tub in master …see more

from $100 / night

$700 / week

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from $100 / night

1