Become a host

Guesthouse vacation rentals in Portland

Find and book unique guesthouse rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Portland guesthouse rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

The exterior of Search-Me-Heart is surrounded by lush greenery and vibrant flowers, with a welcoming sign prominently displayed. The property features a white facade under a clear blue sky, contributing to the tropical garden setting.
Private room in Drapers
4.78 out of 5 average rating, 72 reviews

Search-Me-Heart - China Rose

Guesthouse in Snow Hill

Ferdie's Place - Master Bedroom

An outdoor terrace features a gazebo with a tiled roof, surrounded by lush greenery. Comfortable seating is arranged on the terrace, providing a view of the distant sea under a soft blue sky. The vibrant landscape enhances the serene atmosphere of the space.
Private room in Port Antonio
4.77 out of 5 average rating, 22 reviews

King size bedroom - Sea view & Private balcony

Guesthouse in Snow Hill

Ferdie's Place - Jett Room

A well-maintained pathway, flanked by lush greenery and vibrant flowers, leads to the entrance of the cottage. The entrance is framed by tropical plants, enhancing the welcoming atmosphere. A small sign is visible near the entrance, identifying the residence.
Guesthouse in Kingston

The Main Room at Kingston Cottage

The exterior showcases a charming white building enveloped by lush greenery and colorful flowering plants. The pathway is bordered by vibrant red and pink blooms, leading toward a welcoming entrance sign that reads 'Search-Me-Heart.' A serene tropical setting is evident.
Private room in Drapers PA
4.75 out of 5 average rating, 12 reviews

Search-Me-Heart - Plumbago

The villa is surrounded by vibrant tropical flora, with a clear blue swimming pool reflecting sunlight. Lush palm trees provide shade, and the outdoor gazebo is visible in the background, enhancing the serene atmosphere of the property.
Private room in Port Antonio
4.8 out of 5 average rating, 44 reviews

FAMILY ROOM, Single, Double or Triple, Shared Bath

Superhost
A cozy bedroom is depicted, featuring a spacious bed with striped bedding. Large, slatted doors open to an outdoor space filled with lush greenery, including a palm tree. A comfortable blue chair is positioned near the doorway, enhancing the room's inviting atmosphere.
Private room in Kingston
4.88 out of 5 average rating, 8 reviews

Deluxe Private - Gordon Town Kotch

Guest house rentals with a patio

Private room in Port Antonio
4 out of 5 average rating, 8 reviews

nature twin room

A charming home is nestled among lush greenery, featuring a colorful exterior with red, yellow, and green accents. Sturdy steps lead up to the entrance, which is framed by tropical plants and an inviting porch area with wooden furniture.
Private room in Fair Prospect

Rooms at Rasta Villa

The room features a high vaulted ceiling with wooden beams. Two spacious beds are adorned with light blue and white patterned throws. A wall-mounted television is visible, alongside a fan. The decor includes a coordinating patterned curtain, and a bathroom entry is seen through a doorway.
Private room in Port Antonio
New place to stay

Ocean Crest Guest House -Room 10

Private room in Snow Hill
New place to stay

Garden View - Private Villa Bedroom and Bathroom

The exterior of the property showcases a welcoming facade surrounded by lush greenery and vibrant flowering plants. A sign reading 'Search-Me-Heart' is displayed prominently near the entrance, highlighting the inviting nature of the home.
Private room in Drapers
4.83 out of 5 average rating, 12 reviews

Search-Me-Heart Kiss me Over the Garden

A charming entryway is framed by a decorative metal gate, leading to a colorful house with wooden accents. Lush greenery and tropical plants surround the path, enhancing the welcoming appearance of the home. Sunlight illuminates the exterior, highlighting the intricate window designs and porch area.
Guesthouse in Port Antonio

Mesmerize Guest House

Guest favorite
A cozy bedroom features a spacious bed adorned with a striped blanket. Natural light filters through the open wooden doors, which reveal a lush green view outside. A nightstand is positioned beside the bed, contributing to the serene atmosphere.
Private room in Gordon Town
4.95 out of 5 average rating, 21 reviews

Queen Private-Gordon Town Kotch

The exterior features a bright blue wall with white accents and arches, providing a clean and inviting entrance. A wooden door leads into the cottage, with several windows allowing natural light to enter. A stairway is visible leading to the upper level.
Guesthouse in Manchioneal

Diamond Cozy Cottage

Guest house rentals with a washer and dryer

Top guest favorite
Vibrant purple orchids are prominently displayed in the foreground, with a lush garden environment surrounding a clear swimming pool in the background. Tropical plants and trees are seen throughout the scene, contributing to a serene outdoor atmosphere.
Guesthouse in Kingston
4.95 out of 5 average rating, 152 reviews

Orchid Cottage

A well-lit living area features a comfortable blue sofa and a wicker chair, complemented by a white coffee table. A wooden dining table with white chairs is visible, alongside a TV unit. Lush greenery is seen through the large window.
Guesthouse in Port Antonio

Star San Lower, Blue Lagoon Jamaica

A tranquil pool area features a curved pool surrounded by lush greenery and palm trees. Comfortable lounge chairs are positioned on the stone patio, inviting relaxation. A charming cottage with arched windows is seen in the background, complementing the serene outdoor setting.
Guesthouse in Kingston

Escape Place

A white dresser with three spacious drawers is positioned beside a modern black lamp. A decorative mirror reflects light in the cozy studio space, while a gray chair adorned with a patterned pillow adds a touch of style to the room.
Private room in Kingston

Luxury Casita

The elegant two-story Villa Blanca is presented with cream-colored walls and intricate decorative railings. A spacious wraparound balcony is visible, offering inviting outdoor space. Lush greenery surrounds the property, while the secure iron gate frames the entrance, enhancing the home's appeal in a quiet neighborhood.
Guesthouse in Old Harbour

Villa Blanca

Top guest favorite
A modern kitchen is equipped with stainless steel appliances, including a microwave and a large refrigerator. A sleek countertop with bar seating and a stylish stovetop complements the cabinetry. Natural light filters through a window with a soft gray valance, enhancing a functional cooking space.
Guesthouse in Old Harbour
5 out of 5 average rating, 8 reviews

The Chateau Guesthouse- Old Harbour

A sunny outdoor area is highlighted by a sparkling swimming pool surrounded by lounge chairs. Lush greenery and vibrant flowers are present, with palm trees adding to the tropical ambiance. The villa's structure is visible in the background under a clear blue sky.
Private room in Port Antonio
4.7 out of 5 average rating, 53 reviews

King-Size bedroom - 10 min walk Frenchman's Cove

The exterior of a two-story guest house is depicted, featuring a warm-toned façade with decorative arches. Steps lead to an ornate entrance, framed by potted plants. Balconies adorned with railings overlook the surrounding greenery, enhancing the welcoming ambiance of the property.
Private room in Zion Hill

MuMatt Guest House

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. Portland
  4. Guesthouse rentals