We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Kailua

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 km
185 rentals in Kailua.
Sort by:
Tripadvisor Sort

Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10)

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Kailua Beach Front - Licensed TVU Available for Nightly Rent

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Walker's Lanikai Beach House~Oceanfront restored Historic home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Adorable Beachfront Home with Gorgeous Ocean Views

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

'Koi Palms Luxury Cottage' Short Walk to Kailua Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Lanikai Cottage on Secluded Quiet Beach with Amazing Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Enchanting Beach Bungalow with Private Garden

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Kailua rentals sent straight to your email!

Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out

Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Perfect Oasis, Steps To The Beach! 100% Solar!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Barefoot living on Lanikai Beach -- BEACHFRONT!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Kailua Beach Vacation Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

1 house from the beach - solar heated pool - AC - Contact Owner for Rates

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

KAILUA-STEPS TO THE BEACH

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Come Relax just Steps from the Beach!!!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Close to the Beautiful Kailua Beach-A/C-Full Kitchen-WiFi-Covered Patio-Laundry

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Private Beachside Kailua Home - Remodeled w/AC - 3 min walk to beach!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Happy House on Exquisite Kailua Beachside Property!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Footsteps to Hawaii's Best Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Bring your aloha shirt and visit Kailua TAX I.D.W********-01 NUC 90/BB-0069

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Blue Ginger Cottage/Mele Hale

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

BEST DEAL ON LANIKAI BEACH!!! Footwear optional...

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

CHRISTMAS DATES AVAILABLE!! Prime Location Across from Kailua Beach Park w/AC

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

This House Has It All - Location, Pool, Renovated, Steps From Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

5 Minute Walk to Kailua Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Close to beach, sleeps 2, AC, quiet, private

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Gorgeous Views and Home. Minutes from Lanikai Beach in Kailua.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Kahela - Paradise for Rent

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Luxury Home in Gated Community Steps from Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Nancy's Kailua Cottage Mauka

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

ONE BOOKING PER 30 DAYS. INQUIRE TO CLARIFY AND FOR MONTHLY.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Beachside Kailua, Immaculate & Private 1 BR, stones throw to Kailua Beach!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Available and legal for stays less than 30 days

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Kailua Beach Park Cottage - 2BR

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Kaimana Cottage - Walking Distance to beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Martins Hale - Private 1 Bedroom Studio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Kimos beach house Lovely renovated home and 10 min walk to the beach.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Beautiful Kailua Home, looking for a family to share it's Aloha

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

8 bd 5 ba Beachside Retreat - Steps from Kailua Beach - Professionally managed

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
PreviousNext
1234
Frequently Asked Questions about Kailua