Owner Direct Vacation Rentals in San Juan

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  4.  Florida
  5.  Fort Walton Beach - Destin
  6.  San Juan

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5776 San Juan Vacation Homes From $109

Looking for the ideal vacation rental in San Juan? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Special Purpose by Oversee 30A
Special Purpose by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.0k from San Juan center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$572
Average price / night
Check Availability
Seagrove’s 30A Window to Heaven: Pool and Beach
Seagrove’s 30A Window to Heaven: Pool and Beach
House
Santa Rosa Beach, FL, 32459, United States
0.0k from San Juan center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$1356
Average price / night
Check Availability
Flip Flop Cottage - Great rates and dog friendly with additional pet fee
Flip Flop Cottage - Great rates and dog friendly with additional pet fee
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Accommodations, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
1.0

Review score

1 reviews

$109
Average price / night
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Luxe Beach Retreat Walk to Beach Pool Spa, Golf Cart, Game Room & Putting Green
Luxe Beach Retreat Walk to Beach Pool Spa, Golf Cart, Game Room & Putting Green
House
Santa Rosa Beach, FL, 32459, United States
0.0k from San Juan center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

7 Bedrooms22 Guests
10.0

Exceptional

12 reviews

$1748
Average price / night
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NEW Listing! 4 BR/3.5 BA, SLEEPS 10, HEATED SALT WATER POOL
NEW Listing! 4 BR/3.5 BA, SLEEPS 10, HEATED SALT WATER POOL
House
Seagrove Beach, FL, USA
0.1k from San Juan center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$763
Average price / night
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Special Purpose - Private Pool, 2 Beach Cruisers
Special Purpose - Private Pool, 2 Beach Cruisers
House
Santa Rosa Beach, FL, 32459, United States
0.0k from San Juan center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.8

Exceptional

17 reviews

$487
Average price / night
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Casa Playa by Oversee 30A
Casa Playa by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Sports/Activities, Security/Safety, Internet, Parking, Pool, Laundry, Air Conditioner

1 Bedroom6 Guests
New to Booking
$409
Average price / night
Check Availability
Seagrove- 4 BR, Private Heated Salt Water Pool, Beach Access, Golf Cart and Bikes
Seagrove- 4 BR, Private Heated Salt Water Pool, Beach Access, Golf Cart and Bikes
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$2402
Average price / night
Check Availability
Coconut Cove by Oversee 30A
Coconut Cove by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Security/Safety, Internet, Pool, Laundry, Parking, Air Conditioner, Child Friendly

5 Bedrooms12 Guests
New to Booking
$1385
Average price / night
Check Availability
Slim Shady + Pool, Golf Cart, Easy Access & Bikes
Slim Shady + Pool, Golf Cart, Easy Access & Bikes
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
9.4

Superb

3 reviews

$1001
Average price / night
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Slim Shady by Oversee 30A
Slim Shady by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom14 Guests
New to Booking
$1252
Average price / night
Check Availability
30A - Walk to Beach - Pool - Golf Cart - Bikes
30A - Walk to Beach - Pool - Golf Cart - Bikes
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$883
Average price / night
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Sun Palace by Oversee 30A
Sun Palace by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom2 Guests
New to Booking
$333
Average price / night
Check Availability
Classic Beach Home With Heated Private Pool - Sleeps 9
Classic Beach Home With Heated Private Pool - Sleeps 9
House
250 N Andalusia Ave, Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Heater, Internet, No Smoking

10.0

Exceptional

1 reviews

$1220
Average price / night
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Winters End by Oversee 30A
Winters End by Oversee 30A
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$932
Average price / night
Check Availability
2 Bikes~ Newly renovated Pool~Bike to Seaside
2 Bikes~ Newly renovated Pool~Bike to Seaside
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$542
Average price / night
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Seagrove - Texas Tide
Seagrove - Texas Tide
House
Santa Rosa Beach, FL, USA
0.1k from San Juan center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms11 Guests
New to Booking
$579
Average price / night
Check Availability
Sand Wand | 5 Beds | 5.5 Bath | Private Pool | Walk to Beach | Seagrove Beach 30A
Sand Wand | 5 Beds | 5.5 Bath | Private Pool | Walk to Beach | Seagrove Beach 30A
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

5 Bedrooms12 Guests
8.0

Good

1 reviews

$843
Average price / night
Check Availability
Stunning New Main & Carriage House with Private Pool- 59 Barcelona Avenue
Stunning New Main & Carriage House with Private Pool- 59 Barcelona Avenue
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

6 Bedrooms14 Guests
New to Booking
$1424
Average price / night
Check Availability
🌴 3 Minute Walk to Beach | Private Heated Pool | Golf Cart | Amazing Location
🌴 3 Minute Walk to Beach | Private Heated Pool | Golf Cart | Amazing Location
House
Santa Rosa Beach, FL, 32459, United States
0.1k from San Juan center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$920
Average price / night
Check Availability
Modern Pet-Friendly Retreat for Families w/2 Bunk Rooms | Brand New Pool!
Modern Pet-Friendly Retreat for Families w/2 Bunk Rooms | Brand New Pool!
House
Seagrove Beach, FL, 32459, United States
0.1k from San Juan center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1112
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in San Juan.

Where to stay in San Juan? Best neighborhoods & areas

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Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in San Juan. If you plan on staying in the San Juan area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in San Juan

You can explore 5776 verified vacation rentals in San Juan. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in San Juan vary depending on the season, property size, and location. Rates typically start from around $109 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in San Juan include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in San Juan welcome pets. Currently, 24 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in San Juan often include amenities such as Pool, Laundry, and Fireplace/Heating. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.