We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Airbnb your place

Holiday houses in Little Diamond Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Little Diamond Island

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Apartment in Portland

4.88 out of 5 average rating, 377 reviews

Modern East End studio, perfect Portland home base

Enjoy all that Portland has to offer from this clean, modern, and spacious studio in the city's hippest neighborhood. Walk one block to enjoy Duckfat frites at the Oxbow beer garden or head down Washington Ave to sample the best restaurants in Portland including Drifter's Wife, Cong Tu Bot, and Izakaya Minato, among others. Walk 5 mins up Munjoy Hill to picnic on the Eastern Promenade overlooking Casco Bay or 10 mins down into the Old Port. Do it all from this beautiful and private apartment!

19–26 Nov

$254 NZD per night

Guest favourite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

6–13 Feb

$253 NZD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 109 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

10–17 Sep

$229 NZD per night

Guest favourite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

19–26 Jan

$224 NZD per night

Apartment in Portland

4.78 out of 5 average rating, 303 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

5–12 Mar

$219 NZD per night

Guest favourite

Apartment in Portland

4.93 out of 5 average rating, 551 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

20–27 Nov

$192 NZD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 168 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

17–24 Jan

$201 NZD per night

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 195 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

25 Jan – 1 Feb

$204 NZD per night

Guest favourite

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 138 reviews

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

28 Mar – 4 Apr

$318 NZD per night

Guest favourite

Apartment in Portland

4.94 out of 5 average rating, 452 reviews

No cleaning fee! Location, location! And parking!

At Location Location! You can be assured that we take care of all the cleaning… so please be on vacation! This lovely, simple 1 bedroom apartment is in the heart of the Portland's West End. Just around the corner, a foodie paradise! The Danforth bar, Chaval, Pan Men Miyake, Tandem bakery and Local 188 many others. Just down the street, Maine Med,Mercy Hospital, PMA, art galleries, shopping & the Old Port!

5–12 Mar

$180 NZD per night

Guest favourite

Guest suite in Freeport

4.95 out of 5 average rating, 194 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

18–25 May

$135 NZD per night

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 151 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

13–20 Nov

$271 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Little Diamond Island holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Little Diamond Island

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 678 reviews

Oceanfront with amazing views and private entrance

1–8 Oct

$607 NZD per night

Guest favourite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

17–24 Sep

$277 NZD per night

Guest favourite

Apartment in Portland

4.88 out of 5 average rating, 345 reviews

Central-Locale Studio in Vibrant Portland Maine!

15–22 Nov

$307 NZD per night

Guest favourite

Apartment in Portland

4.91 out of 5 average rating, 379 reviews

Private Hill Top Apartment Two/On Street Parking

17–24 Apr

$264 NZD per night

Guest favourite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

19–26 Apr

$221 NZD per night

Apartment in Portland

4.81 out of 5 average rating, 192 reviews

Clean East Bayside Apartment- Amazing Location!!

28 Apr – 3 May

$219 NZD per night

Guest favourite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

4–11 Feb

$134 NZD per night

Guest favourite

Guesthouse in Portland

4.95 out of 5 average rating, 106 reviews

Tiny Island Cottage Hideaway, close to everything

30 Dec – 6 Jan

$465 NZD per night

Destinations to explore