Guesthouse holiday rentals in Culebra

Serene 3 bdrm. Pool w view + perfect for families.

Private, spacious, and light-filled 3 bdrm apartment w/ 10-foot ceilings on top of a quiet hill. 3 min. from beach and 5 min. from the main town of Isabel Segunda. This property was designed for the view! Every day you will be able to see the island, ocean, and the famous Vieques sunset from your private deck or the pool. Beach gear, two snorkel sets, inflatable paddleboard, and Bowflex dbs included. 2 Lg bdrms with comfortable queen beds and 1 bedroom with 2 twin beds. Full kitchen+bbq grill.

Family · Location · Condition

Esperanza Penthouse with a view (Unit 5)

Our recently renovated Penthouse is setup with 2 queen size beds, has a full kitchen combined with living/dining, & a bathroom. The side doors open to a spacious patio. Its only a 7-10 minute walk to the Malecon (the main tourist strip) in Esperanza and is close to the Green Store so you can pick up supplies. We have the fastest wifi that we could get on the island, so guests can stay connected. Tropical gardens on first floor with a mango tree. Brand-new, upgraded Air Conditioner in this unit!

Value · Family · Bathroom

2 Blocks 2 Ferry - twin beds on lighthouse point

Top Ten features past guests loved; 1) no need to rent a vehicle for 1-2 day stay. Located 2 blocks from ferry and public transportation. 2) considered a safe neighborhood 3) ocean on two sides 4) you can hear the waves 5) personal greeting by experienced hostess. 6) Guestbook with money saving tips 7) luggage lockers available for early arrivals late departures 8) a walkable town beach 9) well stocked, includes beach chairs, coolers and beach towels 10) restaurants and shops a short walk

Location · Family · Cleanliness

Charming In-Town Guesthouse

Cozy, centrally located guesthouse tucked behind our main home in the heart of Culebra. Walk to restaurants, bars, cafés, and shops. A simple, comfortable space with vintage touches. The house has been in my family for generations, originally my great-grandmother’s home, and is full of character. In-town sounds are part of the experience: live calypso and music can be heard some nights and roosters in the mornings. Ideal for travelers seeking a walkable, authentic home base while exploring.

Top Guest favourite

Guest favourite

Artist A Frame Casa Mandala #2

Reconnect with nature at this funky unforgettable escape. This is a stand alone 10x12 A frame cabin with the restroom and shower located steps away and offer a boho/eco feel. It is an unique experience close to town with nature that still feels private and secluded. You'll sleep on a queen breatheable memory foam bed in a room that feels cozy with cold air-conditioning. On site secure parking, beach chairs, snorkel masks and beach towels included. Dont take my word for it read the reviews.

Value · Family · Long stay

Casita Coqui • Studio 1 bed/1 bath - Kitchenette

Your own private island escape 🌴 Just a 5–6 minute walk to and from the ferry, this cozy casita studio offers a peaceful, private stay separate from the main house (not occupied during rentals). Enjoy a comfy queen bed with a new memory foam mattress, plus a microwave, mini fridge, coffee maker, and private bath. Walk to the beach, restaurants, and bars—perfect for couples or solo travelers in a safe, well-lit neighborhood. Small cozy space inside with outdoor dining options in carport.

Family · Location · Indoor spaces

Apt 4A Flamenco Beachfront Villas with Ocean View

Discover the hidden gem of Flamenco Beach on Culebra Island. Enjoy crystal-clear turquoise waters, protected coral reefs, and powdery white sand, perfect for snorkeling, swimming, and sunbathing. Relax in the tranquil bay, surrounded by miles of pristine shoreline and breathtaking views. Whether you're seeking adventure or relaxation, Flamenco Beach is the ultimate escape from the daily grind. Join us in paradise and discover why it's one of the Caribbean's most sought-after destinations.

Family · Location · Nearby

Orita: Designer Studio with Art at Playa Negra

Artsy, rustic, jungly and secluded. Cat sanctuary where free roaming felines are cared for. Private studio suite with gorgeous black tub& rain shower, kitchen & outdoor patio on Vieques’ South side, 1.5 miles from Esperanza's restaurants and activities. Located on the lush grounds of Oro Gallery at Playa Negra's entrance, Vieques' only black sand beach. Relax in a queen size bed surrounded by art or cook in your small, well-appointed kitchenette and enjoy the views from outdoor patio.

Family · Location · Decor

Tropical Tranquil Setting - Casita Beija Flor

There is no better place to relax and rejuvanate then in the privacy of your lovely Spanish style casita. Casita Beija Flor was designed with comfort and style in mind. The casita is situated on 4 lush private acres surrounded by vegatation and flowers. It is in the neighborhood of Destino, Vieques. The mid-island location is within easy reach of the towns of Isabel and Esperenca as well as close to the entrance of the stunning Navy beaches. Shopping and restaurants are also close by.

Location · Family · Cleanliness

Magnolia Esperanza Cottage

As seen on HGTV! Enjoy life as a local at Casita Magnolia. Let our cozy studio be your home base for experiencing the delights that Vieques has to offer - secluded beaches, Bio Bay, snorkeling with sea turtles. Start with your morning coffee in the shady, secluded gazebo and plan your adventures for the day. Meals can be prepared in the full kitchen, or savor local foods nearby. Enjoy the sights and sounds of this beautiful quirky small island.

Location · Family · Kitchen

Casita Surf

Puerto Rican owned 🇵🇷 Modern minimalist casita with everything you need just 30 seconds from the beach. Clean, bright, and comfortable with AC, Wi-Fi, and a simple kitchen—perfect for surfers and beach lovers. If conditions line up, the nearby break offers great beginner to intermediate waves. Only a 3-minute drive or 15-minute walk to town for food, coffee, and local spots. Simple, easy, and steps from the ocean.

Value · Location · Indoor spaces

Casa Iguana

A peaceful 1-bedroom studio surrounded by the beautiful island scenery of Vieques, Puerto Rico. With just a 15-minute drive to the beautiful white sandy beaches where you can swim and enjoy snorkeling with the family. Located centrally Villa Borinquen, 10-minute drive to Malecon, where you can enjoy the local restaurants while enjoying the view of the Caribbean Ocean.

Value · Location · Kitchen