Anastasia Island Retreat

Anastasia Island Retreat

3 bedrooms·2 baths
$100 – $162/ night(excl. fees & taxes)
Two House Island Retreat

Two House Island Retreat

5 bedrooms·3 baths
$179 – $1,492/ night(excl. fees & taxes)
Anastasia Island Treehouse

Anastasia Island Treehouse

2 bedrooms·1 bath
$124 – $153/ night(excl. fees & taxes)
The Look-Out - Holiday Home

The Look-Out - Holiday Home

5 bedrooms·4 baths
$179 – $1,659/ night(excl. fees & taxes)
Anastasia Island Villa Duplex| Single Level | EV

Anastasia Island Villa Duplex| Single Level | EV

3 bedrooms·2 baths
$87 – $140/ night(excl. fees & taxes)
Free EV Charging | Upper Level + Private Rooftop

Free EV Charging | Upper Level + Private Rooftop

2 bedrooms·2 baths
$78 – $123/ night(excl. fees & taxes)
Oasis Over the Bridge of Lions

Oasis Over the Bridge of Lions

4 bedrooms·3 baths
$169 – $1,137/ night(excl. fees & taxes)
Work Stay Near Mayo - Game Room - Sleeps 8

Work Stay Near Mayo - Game Room - Sleeps 8

4 bedrooms·2 baths
$141 – $361/ night(excl. fees & taxes)
Private backyard with heated pool

Palms Bungalow: Comfy Mayo Retreat; Heated Pool, Close to Beach

3 bedrooms·2 baths
4.83(12 reviews)
$195 – $405/ night(excl. fees & taxes)
Osprey: Family-Friendly Beach Retreat Heated Pool By Mayo

Osprey: Family-Friendly Beach Retreat Heated Pool By Mayo

4 bedrooms·2 baths
5(6 reviews)
$225 – $1,299/ night(excl. fees & taxes)
Lg 3 bdrm near chic downtown-TIAA stadium

Lg 3 bdrm near chic downtown-TIAA stadium

3 bedrooms·2 baths
4.33(3 reviews)
$195/ night(excl. fees & taxes)
St. Augustine Vacation Rental | 2BR | 1BA | 1,021 Sq Ft | 3 Steps Required

'Palm Bungalow' Near Dtwn St Augustine & Beaches!

2 bedrooms·1 bath
4.58(26 reviews)
$150 – $175/ night(excl. fees & taxes)
Family Retreat Near Beach & Historic St. Augustine image 2

Family Retreat Near Beach & Historic St. Augustine

3 bedrooms·2 baths
$195 – $205/ night(excl. fees & taxes)
Late Night swims under the stars

Treehouse: Spanish Modern Family Beach Retreat w/ Heated Pool

3 bedrooms·2½ baths
5(5 reviews)
$195 – $1,297/ night(excl. fees & taxes)
Overhead shot of PV Escape with pool and backyard retreat

PV Escape: Luxury Escape with Pool & Putting Green

5 bedrooms·3 baths
5(4 reviews)
$405 – $4,595/ night(excl. fees & taxes)
Shiplap Pool Cottage @ Beach 5/2

Shiplap Pool Cottage @ Beach 5/2

5 bedrooms·2 baths
$118 – $750/ night(excl. fees & taxes)
Relax after your day in the sun

Beach Bungalow: Private Pool + Game Room | 1 Mile to Beach

3 bedrooms·2 baths
5(2 reviews)
$225 – $899/ night(excl. fees & taxes)
Bird's-eye view of your private backyard oasis - pool, pickleball court, putting green and plenty of room to play

Pickleball Paradise: Pool, Pickleball & Putting Green Retreat

4 bedrooms·2 baths
5(3 reviews)
$235 – $1,899/ night(excl. fees & taxes)
Coastal Oasis:Family Retreat | Pool, Games + Bike to Beach

Coastal Oasis:Family Retreat | Pool, Games + Bike to Beach

5 bedrooms·3 baths
5(8 reviews)
$275 – $2,499/ night(excl. fees & taxes)
Entrance from Guest House to Main House

8 BR Compound | 2 Pools, Putting Green + Game Rooms

8 bedrooms·5 baths
5(14 reviews)
$708 – $3,398/ night(excl. fees & taxes)
Designed for both relaxing and playing, this backyard has everything you need for the perfect stay.

Pickleball Point: Private Court + Heated Pool = Stay & Play

3 bedrooms·2 baths
$255 – $1,499/ night(excl. fees & taxes)
Bird's-eye view of your private backyard oasis - 2 pools, 2 pickleball courts, 2 putting greens, 2 fire pits - one unforgettable vacation

Twin Court Retreat: 2 homes • 2 Pools • 2 Courts • Sleeps 18

7 bedrooms·4 baths
$598 – $3,595/ night(excl. fees & taxes)
The Perfect One Night Private Studio • JaxPort & Vystar

The Perfect One Night Private Studio • JaxPort & Vystar

1 bedroom·1 bath
$70 – $201/ night(excl. fees & taxes)
From above, you can see the thoughtfully designed outdoor retreat with a sparkling heated pool, fire pit for gathering, putting green, tropical landscaping, and multiple spaces for gathering and relaxing.

Islander: Private Beach Bar Vibes | Pool, Grill + Games

4 bedrooms·2½ baths
5(1 review)
$275 – $1,899/ night(excl. fees & taxes)