Welcome to Joyful-Stays, Historic St Augustine! Come stay at our home away from home, and walk to the historic sites of Flagler college, Lightner Museum, and St George Street!
This couch is a new queen sleeper sofa, pretty comfortable, if more sleep spaces are needed!
Brand New hot tub for 2-3 people
<10 minutes walk to St George Street.
Enjoy the fully stocked kitchen, with all the conveniences of home including a blender, a coffee station, pots, pans, serveware, and bakeware!

St Augustine.

3 bedrooms·2½ baths
St. Augustine • Florida
5(2 reviews)

$1,373.12 USD $1,338.65 USD total for 3 nights

Dec 13 – 16, 2026

Nights of lights
Living Room
Kitchen
Exterior
Tesla Wall Connector

Walk to Nights of Lights, trolley #11 + EV charger

2 bedrooms·2 baths
St. Augustine • Florida
5(64 reviews)

$697.26 USD total for 3 nights

Nov 17 – 20, 2026

ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow

ST. Sylvan Historic Bungalow

2 bedrooms·1 bath
St. Augustine • Florida

$680.00 USD total for 3 nights

Nov 12 – 15, 2026

Private fully fenced yard, hot tub, BBQ and fire pit
4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed
4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed
Games for the family
Fully fenced yard with yard games, hot tub, BBQ, outdoor seating and fire pit

4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed

4 bedrooms·2 baths
St. Augustine • Florida
5(76 reviews)

$1,092.46 USD total for 3 nights

Nov 15 – 18, 2026

Encanto — A Cheerful Coastal Getaway in Full Bloom
A storybook setting for every meal—sunny, floral, and effortlessly inviting.
Charming Cottage: Bright exterior with vibrant plants and a welcoming turquoise door awaits you!
Morning or night, your grill’s always ready.
Encanto — A Cheerful Coastal Getaway in Full Bloom

Encanto — A Cheerful Coastal Getaway in Full Bloom

3 bedrooms·2 baths
St. Augustine • Florida
5(40 reviews)

$1,178.23 USD total for 3 nights

Nov 12 – 15, 2026

Welcome! Sunny retreat with a welcoming porch, native plants & coastal charm.
Charming First Impression Casita’s bright exterior, welcoming porch seating, and cheerful landscaping set the tone for a stay filled with warmth, style, and St. Augustine charm from the moment you arrive.
Casita Augustina — A Coastal Cottage with a Hidden Courtyard
Casita Augustina — A Coastal Cottage with a Hidden Courtyard
Waffle Station Delight: Yummy and charming - perfect for a relaxed mornings!

Casita Augustina — A Coastal Cottage with a Hidden Courtyard

3 bedrooms·2 baths
St. Augustine • Florida

$1,137.22 USD total for 3 nights

Nov 12 – 15, 2026

Serene Swing Under the Oaks Nestled beneath centuries-old oaks draped in Spanish moss, this cozy swing invites you to relax, read, or simply sway with the breeze—a peaceful backyard nook made for slow moments and lasting memories.
Charming First Impression Casita’s bright exterior, welcoming porch seating, and cheerful landscaping set the tone for a stay filled with warmth, style, and St. Augustine charm from the moment you arrive.
Sunshine Duo — Two Coastal Homes Just Down the Road
Two Homes, 1 booking, 0.3 miles apart. Homes for togetherness with privacy!
Cook, dine, and unwind in a fully stocked kitchen designed for effortless meals.

Sunshine Duo — Two Coastal Homes Just Down the Road

6 bedrooms·4 baths
St. Augustine • Florida

$2,615.84 USD total for 3 nights

Nov 12 – 15, 2026

La Costa — A Modern Coastal Retreat with a Putting Green
La Costa — A Modern Coastal Retreat with a Putting Green
Views of lush greenery
Modern backyard oasis with putting green, hammock & fenced patio
Private palm-lined yard with putting green, hammock & lounge

La Costa — A Modern Coastal Retreat with a Putting Green

3 bedrooms·2 baths
St. Augustine • Florida

$1,227.87 USD total for 3 nights

Nov 12 – 15, 2026

Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat

Anastasia Island Retreat

3 bedrooms·2 baths
St. Augustine • Florida
The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home

The Look-Out - Holiday Home

5 bedrooms·4 baths
St. Augustine • Florida

$1,496.00 USD total for 3 nights

Nov 12 – 15, 2026

Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop

Free EV Charging | Upper Level + Private Rooftop

2 bedrooms·2 baths
St. Augustine • Florida
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

3 bedrooms·2 baths
St. Augustine • Florida

$665.61 USD total for 3 nights

Nov 15 – 18, 2026

St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown

St Augustine whole house w/ hot tub near downtown

5 bedrooms·4 baths
St. Augustine • Florida

$1,718.10 USD total for 3 nights

Nov 15 – 18, 2026

2BD, Pool+Spa, Walk to beach, Putput, Kayaks image 1
2BD, Pool+Spa, Walk to beach, Putput, Kayaks image 2
2BD, Pool+Spa, Walk to beach, Putput, Kayaks image 3
2BD, Pool+Spa, Walk to beach, Putput, Kayaks image 4
6 Passenger Golf Cart available to rent.

2BD, Pool+Spa, Walk to beach, Putput, Kayaks

2 bedrooms·2 baths
St. Augustine • Florida
5(29 reviews)

$2,320.15 USD total for 5 nights

Dec 6 – 11, 2026

Casa Del Sol - Luxury & Convenience
Casa Del Sol - Luxury & Convenience
Casa Del Sol - Luxury & Convenience
Casa Del Sol - Luxury & Convenience
Casa Del Sol - Luxury & Convenience

Casa Del Sol - Luxury & Convenience

7 bedrooms·3½ baths
St. Augustine • Florida
5(123 reviews)

$3,082.69 USD total for 3 nights

Nov 15 – 18, 2026

14BD/11BA Vilano Retreat steps from the Beach!
HUGE professional putting green, fully fenced & turfed backyard, hammock, and plenty of games to keep kids and adults alike entertained!
Brand new paver walkway was added in March 2023
14BD/11BA Vilano Retreat steps from the Beach!
High end metal artwork is outstanding in this home! We love the open concept living where the kitchen, living area, and dining area all flow together but yet defined enough to create its own space.

14BD/11BA Vilano Retreat steps from the Beach!

14 bedrooms·11 baths
St. Augustine • Florida
5(2 reviews)

$10,777.00 USD total for 3 nights

Nov 12 – 15, 2026

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 1
5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 2
Open floor plan
Who knew hanging out in a garage could be so fun!
5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 5

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM!

5 bedrooms·3 baths
St. Augustine • Florida
5(38 reviews)

$2,108.99 USD total for 3 nights

Nov 12 – 15, 2026

Multiple King Suites, WALK 2 beach, Dream backyard image 1
Multiple King Suites, WALK 2 beach, Dream backyard image 2
Multiple King Suites, WALK 2 beach, Dream backyard image 3
Multiple King Suites, WALK 2 beach, Dream backyard image 4
Multiple King Suites, WALK 2 beach, Dream backyard image 5

Multiple King Suites, WALK 2 beach, Dream backyard

5 bedrooms·4 baths
St. Augustine • Florida
5(8 reviews)

$2,108.99 USD total for 3 nights

Nov 12 – 15, 2026

12x25' heated, salt water pool with sunledge. We love having the enclosure as we can enjoy it anytime of day with no pesky bugs!
HUGE professional putting green, fully fenced & turfed backyard, hammock, and plenty of games to keep kids and adults alike entertained!
Brand new paver walkway was added in March 2023
Casa del Paraiso - 7BD/5BA Premier Escape!
High end metal artwork is outstanding in this home! We love the open concept living where the kitchen, living area, and dining area all flow together but yet defined enough to create its own space.

Casa del Paraiso - 7BD/5BA Premier Escape!

7 bedrooms·5 baths
St. Augustine • Florida
5(40 reviews)

$2,904.27 USD total for 3 nights

Nov 15 – 18, 2026

Private walkover from our complex to the beach.
Main living room with 65 inch Flatscreen TV.
Updated Beach Condo - Snowbirds Welcome image 3
Additional seating for 4 at the bar.
Updated Beach Condo - Snowbirds Welcome image 5

Coral Condo at The Ocean Gallery

2 bedrooms·2 baths
St. Augustine • Florida
4.91(11 reviews)

$1,250.00 USD total for 5 nights

Jan 9 – 14, 2027

The Pelicans Way
The Pelicans Way
The Pelicans Way
The Pelicans Way
The Pelicans Way

The Pelicans Way

2 bedrooms·2 baths
St. Augustine • Florida
5(5 reviews)

$721.35 USD total for 3 nights

Nov 16 – 19, 2026

Pool + Spa • Walk to Beach • Pet Friendly image 1
Pool + Spa • Walk to Beach • Pet Friendly image 2
Unwind in our brand-new saltwater spa, the perfect way to soak, relax, and recharge after a day at Crescent Beach.
Our cozy open-concept living room features a TV, board games, books, and coastal oyster wallpaper, creating a relaxing space to unwind, watch a movie, read, or enjoy game night with family and friends.
Our cozy open-concept living room features a TV, board games, books, and coastal oyster wallpaper, creating a relaxing space to unwind, watch a movie, read, or enjoy game night with family and friends.

Pool + Spa • Walk to Beach • Pet Friendly

3 bedrooms·2 baths
St. Augustine • Florida
5(27 reviews)

$1,535.00 USD total for 3 nights

Nov 12 – 15, 2026

Plenty of seating around the pool including four loungers, four adirondacks & bar top table for four.
Game room with NBA All-Stars & Golden Tee Arcade games, pool table, karaoke, Roku TV.
Dine al fresco and experience a jaw dropping sunsets over the intracoastal waterway.
Primary suite with a king bed and extra soft linens.
HGTV inspired design living area w/plenty of seating and stunning water views.

After Hours Retreat

4 bedrooms·4 baths
St. Augustine • Florida

$1,626.93 USD total for 3 nights

Nov 30 – Dec 3, 2026

The beautiful Guana preserve! You can hear the ocean in the backdrop!
Cozy King Size Bed
Modern Beach Suite!
Beautiful Sunsets and Sunrises while you listen to Ocean Waves across the preserve! Picture is to show the sunset / hammock is not there now
Bubbling hot tub

5minTPC/WalkBeach/HotTub/Views

1 bedroom·1 bath
St. Johns County • Florida

$643.90 USD total for 3 nights

Nov 17 – 20, 2026