Photo by Shannon Willitts

Search Guest Houses in Roosevelt Roads from CA $74

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Roosevelt Roads guest houses

A beach scene with a palm tree, clear blue water, and a distant island.

1. Waterside Inn

Waterside Inn
2.0 star property
Esperanza
7.8 out of 10, Good, (297 reviews)
"Very nice place to stay."
United States
Hong
The price is CA $130
CA $142 total
includes taxes & fees
Nov 17 - Nov 18
Waterside Inn
A beach with clear turquoise waters, waves crashing onto the shore, and a rocky cliff with vegetation in the background.

2. The Vieques Guesthouse

The Vieques Guesthouse
3.0 star property
Esperanza
9.8 out of 10, Exceptional, (590 reviews)
"The owner is very friendly and helpful. The place is very clean and close to the best area in Vieques."
United States
Lynette
The price is CA $213
CA $243 total
includes taxes & fees
Nov 13 - Nov 14
The Vieques Guesthouse
A bar area with a view of the sea, bar stools, and a wooden ceiling.

3. Trade Winds Restaurant & Guesthouse

Trade Winds Restaurant & Guesthouse
3.0 star property
Esperanza
8.0 out of 10, Very good, (145 reviews)
"Cozy"
United States
Kyle
The price is CA $121
CA $132 total
includes taxes & fees
Nov 21 - Nov 22
Trade Winds Restaurant & Guesthouse
A modern building with a balcony, outdoor seating, and a well-maintained garden.

4. Mata e' Platano Guesthouse

Mata e' Platano Guesthouse
3.5 star property
Mata de Plátano
9.0 out of 10, Wonderful, (263 reviews)
"This place was very private and has an amazing view of the mountains. Clean room, nice pool and only about 7 min from the town!"
United States
Jacqueline
The price is CA $135
CA $306 total
includes taxes & fees
Nov 29 - Nov 30
Mata e' Platano Guesthouse
A room with a sofa, two chairs, a coffee table, and a large abstract painting on the wall.

5. Vieques Tropical Guest House

Vieques Tropical Guest House
2.0 star property
Isabel II
8.0 out of 10, Very good, (90 reviews)
"Great place!"
United States
Leticia
The price is CA $74
CA $163 total
includes taxes & fees
Nov 17 - Nov 18
Vieques Tropical Guest House
A patio area with a table and chairs, surrounded by greenery.

6. Villa Coral

Villa Coral
3.5 star property
Esperanza
8.8 out of 10, Excellent, (546 reviews)
"Hola, great location. The room had everything we need. We were able to do an early check-in, a huge plus to us. Thank you team 🙏"
United States
Angel
The price is CA $168
CA $183 total
includes taxes & fees
Nov 15 - Nov 16
Villa Coral
A pathway leading to a black gate labeled 'SECRET GARDEN' with lush greenery and a palm tree in the background.

7. Sonsoleá Host

Sonsoleá Host
4.0 star property
Barrio Pueblo
9.8 out of 10, Exceptional, (10 reviews)
"The Best place you can stay at"
United States
German Bonilla
The price is CA $127
CA $290 total
includes taxes & fees
Nov 30 - Dec 1
Sonsoleá Host
An aerial view of a swimming pool area with multiple umbrellas and lounge chairs.

8. CALIZO VIP GUEST HOUSE

CALIZO VIP GUEST HOUSE
4.0 star property
Cabezas
8.8 out of 10, Excellent, (107 reviews)
"Great stay! Comfy beds and strong AC. The courtyard and small pool were beautiful especially from the balcony’s. Walking distance to a lovely beach (one small stretch did not have a sidewalk). One note is that the blinds are not easily opened so there is not much natural light inside the rooms."
United States
Melissa
The price is CA $185
CA $425 total
includes taxes & fees
Nov 12 - Nov 13
CALIZO VIP GUEST HOUSE
A waterfront property with a dock, a boat, and a building with a balcony.

9. Mamacita's Guest House

Mamacita's Guest House
2.5 star property
Culebra Pueblo
8.2 out of 10, Very good, (660 reviews)
"Super place to stay for a few days are a week"
United States
Jeff
The price is CA $171
CA $207 total
includes taxes & fees
Dec 12 - Dec 13
Mamacita's Guest House
A balcony with wicker chairs and a table, overlooking a parking area and a marina with boats.

10. Sueños del Mar Vacation Rentals

Sueños del Mar Vacation Rentals
3.0 star property
Cabezas
9.0 out of 10, Wonderful, (492 reviews)
"The room was clean spacious comfortable enough for one day."
United States
ruth
The price is CA $223
CA $239 total
includes taxes & fees
Dec 12 - Dec 13
Sueños del Mar Vacation Rentals
A colorful building with a balcony, surrounded by greenery.

11. Calizo VIP Boutique Hotel & Guesthouse #5

Calizo VIP Boutique Hotel & Guesthouse #5
Cabezas
9.0 out of 10, Wonderful, (14 reviews)
"Cute place."
United States
Efrain
The price is CA $165
CA $272 total
includes taxes & fees
Nov 17 - Nov 18
Calizo VIP Boutique Hotel & Guesthouse #5
A modern building with a balcony, large windows, and a well-maintained garden with rocks and plants.

12. Mata e` Plátano Villa 05

Mata e` Plátano Villa 05
Mata de Plátano
10.0 out of 10, Exceptional, (3 reviews)
"Perfect little jungle escape "
United States
Tatiana A.
The price is CA $213
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
Mata e` Plátano Villa 05
A modern building with a balcony, large windows, and a well-maintained garden.

13. Mata e` Plátano Villa 06

Mata e` Plátano Villa 06
Sabana
The price is CA $213
CA $359 total
includes taxes & fees
Nov 15 - Nov 16
Mata e` Plátano Villa 06
A modern building with a balcony, large windows, and a well-maintained garden.

14. Mata e` Plátano Villa 08

Mata e` Plátano Villa 08
Mata de Plátano
9.4 out of 10, Exceptional, (3 reviews)
"This was our second stay, and honestly we loved it so much we planned extra time this time just to relax and enjoy! I hope this will always be part of our trips to Puerto Rico!"
United States
Alyssa L.
The price is CA $219
CA $376 total
includes taxes & fees
Nov 23 - Nov 24
Mata e` Plátano Villa 08
A modern building with a balcony, large windows, and a well-maintained garden with rocks and plants.

15. Mata e` Plátano Villa 02

Mata e` Plátano Villa 02
Mata de Plátano
The price is CA $213
CA $359 total
includes taxes & fees
Nov 15 - Nov 16
Mata e` Plátano Villa 02
A modern building with a balcony, large windows, and a well-maintained garden.

16. Mata e` Plátano Villa 04

Mata e` Plátano Villa 04
Mata de Plátano
The price is CA $213
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
Mata e` Plátano Villa 04
A modern building with a balcony, large windows, and a well-maintained garden.

17. Mata e` Plátano Villa 07

Mata e` Plátano Villa 07
Mata de Plátano
2.0 out of 10, (1 review)
"The place was tiny. It was actually a shipping container converted into a room. You can barely walk inside. No cleaning service was provided. False advertisement pictures show the room much much bigger than what it actually is. So frustrated with the customer service and their attitude. I had to cancel my stay after three nights and find somewhere else for the rest of the vacation. Please read the description carefully and also look at the other reviews before booking. You'll be so frustrated."
United States
Mohammed
The price is CA $213
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
Mata e` Plátano Villa 07
A modern building with a balcony, large windows, and a well-maintained garden with rocks and plants.

18. Mata e` Plátano Villa 03

Mata e` Plátano Villa 03
Mata de Plátano
The price is CA $212
CA $368 total
includes taxes & fees
Nov 28 - Nov 29
Mata e` Plátano Villa 03
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.
View all properties

Learn more about Roosevelt Roads

Explore attractions like Ceiba Ferry Terminal and Playa Blanca as you discover things to see and do in Roosevelt Roads.

See all hotels in Roosevelt Roads
An aerial view of a tropical island with clear turquoise waters and a sandy beach.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Top reviews in Roosevelt Roads

A beach with clear turquoise waters, waves crashing onto the shore, and a rocky cliff with vegetation in the background.
The Vieques Guesthouse

The Vieques Guesthouse

The Vieques Guesthouse
Esperanza

10/10 Excellent

Definitely the best place to stay in Esperanza. Super hospitable and friendly hosts!!
Canada
Musab
Reviewed May 17, 2025
The Vieques Guesthouse

Explore a world of travel with Expedia