Find Hotels with Connecting Rooms in Old San Juan

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Old San Juan Hotels with Connecting Rooms

This weekend
Next weekend

Top Old San Juan Hotels with Connecting Rooms

La Terraza de San Juan

3.5 star property
Old San Juan
8.2 out of 10, Very Good, (1000)
"Right in the heart of Old San Juan. You can’t beat the charm and location. "
United States
Bridget
$132 nightly
The price is $143
Dec 10 - Dec 11
Total with taxes and fees
La Terraza de San Juan

S.J. Suites Hotel

3.0 star property
Old San Juan
7.8 out of 10, Good, (399)
"Lovely staff, and very clean "
Canada
Michelle
$157 nightly
The price is $172
Dec 10 - Dec 11
Total with taxes and fees
S.J. Suites Hotel

Hotel El Convento

4.5 star property
Old San Juan
9.0 out of 10, Wonderful, (1002)
"Fantastic place, location, room, and staff."
United States
John
$309 nightly
The price is $337
Dec 10 - Dec 11
Total with taxes and fees
Hotel El Convento

Residences at Dorado Beach, a Ritz-Carlton Reserve

5.0 star property
Higuillar
10.0 out of 10, Exceptional, (2)
"Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans. "
United States
Marina
Residences at Dorado Beach, a Ritz-Carlton Reserve

San Juan Airport Hotel

3.0 star property
Isla Verde
8.4 out of 10, Very Good, (5383)
"Clean room, very friendly staff especially the assistant manager of restaurant/bar. "
United States
Karrie M
$233 nightly
The price is $252
Jan 1 - Jan 2, 2026
Total with taxes and fees
San Juan Airport Hotel

Somos Hotel - San Juan

2.0 star property
Santurce
8.6 out of 10, Excellent, (284)
"Nice staff, great location"
United States
Clara
$114 nightly
The price is $125
Dec 11 - Dec 12
Total with taxes and fees
Somos Hotel - San Juan

Costa Bahia Hotel Paseo Caribe

3.5 star property
San Juan Antiguo
7.4 out of 10, Good, (3664)
"Good prices for rooms."
United States
Glendalis
$131 nightly
The price is $142
Dec 8 - Dec 9
Total with taxes and fees
Costa Bahia Hotel Paseo Caribe

Holiday Inn Express San Juan Condado by IHG

3.5 star property
Condado
8.6 out of 10, Excellent, (1000)
"Staff was helpful, rooms very clean."
United States
wendy
$186 nightly
The price is $203
Dec 16 - Dec 17
Total with taxes and fees
Holiday Inn Express San Juan Condado by IHG

Residence Inn by Marriott San Juan Isla Verde

3.5 star property
Isla Verde
8.8 out of 10, Excellent, (2290)
"The texting support throughout the stay was very beneficial, and this is distinct to Marriott hotels."
United States
Cambria Marie
$284 nightly
The price is $310
Dec 14 - Dec 15
Total with taxes and fees
Residence Inn by Marriott San Juan Isla Verde

Serena Boutique Hotel

3.5 star property
Aguas Buenas
9.4 out of 10, Exceptional, (225)
"We loved the view The owner cooked my breakfast and interacted with the guests on a personal level. Very down home atmosphere. This was an amazing experience for me and my wife. We will stay here again ❤️ loved the hospitality Thank you for a great vacation The owner was very helpful with places to visit for entertainment and food. "
United States
George
$244 nightly
The price is $267
Dec 13 - Dec 14
Total with taxes and fees
Serena Boutique Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Old San Juan

Discover top Old San Juan attractions

Old San Juan, with its cobblestone streets and vibrant historic architecture, offers a rich tapestry of experiences for travelers. Start your journey at El Morro, a historic fortress perched on the cliffs overlooking the Atlantic, where you can wander through its ancient walls and soak in panoramic views that are perfect for family photos. Next, explore the colorful streets adorned with murals and charming shops before stopping at La Fortaleza, the official residence of the Governor, where the beautifully landscaped gardens give a glimpse into the island's history. The San Juan Cathedral, one of the oldest in the Americas, invites you to marvel at its stunning architecture and serene atmosphere. For a taste of local culture, visit the bustling Mercado de San Juan, where you can sample delicious street food and shop for handmade crafts. When it comes to accommodations, the hotels in Old San Juan blend historic charm with modern luxury—imagine waking up to views of the San Juan Bay and enjoying a sumptuous breakfast on a rooftop terrace. With attentive staff ready to assist with your every need, you’ll feel pampered during your stay. Old San Juan promises both adventure and relaxation, making it a perfect escape for families and alike.

Find the best hotels with connecting rooms in Old San Juan

Travelers seeking spacious rooms for family or group gatherings will find these top hotels in Old San Juan ideal, each offering convenient connecting room options for a seamless stay.

Hotel El Convento

  • Why it's great for extra space: Hotel El Convento is a splendid choice for travelers looking for connecting rooms in the heart of Old San Juan. With a remarkable guest review rating of 9.0, this historic hotel provides an elegant stay combined with modern amenities. Guests can enjoy the luxury of connecting rooms, ensuring ample space for families or groups, along with a beautiful outdoor pool that invites relaxation after a day of exploring.
  • Other amenities: In addition to connecting rooms, Hotel El Convento features a delightful terrace for enjoying the stunning views, free internet access, and daily housekeeping to ensure comfort. The hotel is situated in a historical district, surrounded by shopping options, and offers activities such as kayaking, snorkeling, and boat tours nearby. For added convenience, guests can take advantage of babysitting services, luxurious bathrobes, designer toiletries, and fitness facilities.
  • Neighborhood: Old San Juan
  • Nearby attractions: Catedral Basilica Menor de San Juan Bautista - 0.03 miles, San Juan Gate - 0.14 miles, La Fortaleza - 0.19 miles

La Terraza de San Juan

  • Why it's great for extra space: La Terraza de San Juan is perfect for travelers seeking connecting rooms without sacrificing charm and comfort. With a solid review rating of 8.2, this historic hotel design has a welcoming atmosphere complemented by outdoor pools and spacious rooms for families. The hotel’s connecting rooms make it an excellent choice for larger groups looking to stay close together while enjoying their own private space.
  • Other amenities: Beyond the connecting room options, guests can indulge in a rooftop terrace, enjoy breakfast designed for children, and benefit from free cribs or playpens for the little ones. The hotel also features convenient amenities such as express check-in, daily housekeeping, and a poolside bar for refreshing drinks. Located in a historical district, travelers can explore the area’s rich culture while enjoying the comfort of premium bedding and separate living rooms in select suites.
  • Neighborhood: Old San Juan
  • Nearby attractions: Catedral Basilica Menor de San Juan Bautista - 0.22 miles, San Juan Gate - 0.33 miles, La Fortaleza - 0.38 miles

Top Old San Juan Hotel Reviews

Frequently asked questions

Why book your hotel with connecting rooms in Old San Juan with Expedia?
With Expedia, it's easy to find your dream hotel with connecting rooms in Old San Juan. Taking the kids on a break? Find your way to the filters to search for stays with a pool or a water park. If you have a set budget, click on how much you want to spend and the preferred star rating of your hotel. We'll help you find the right place whatever your escape looks like.
How can I find cheap hotels with connecting rooms in Old San Juan?
The best way to track down cheap hotels with connecting rooms in Old San Juan is with Expedia's handy filter tool. Refine your search results by star rating, budget and amenities to land unbeatable deals in a couple of clicks.

Explore a world of travel with Expedia