Title: Cheerful Island Bungalow, Lanai and Walk to Holmes Beach - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=115950806&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Cheerful Island Bungalow, Lanai and Walk to Holmes Beach Villa in Holmes Beach with kitchen and patio ## Photo gallery for Cheerful Island Bungalow, Lanai and Walk to Holmes Beach ![Terrace/patio - Cheerful Island Bungalow, Lanai and Walk to Holmes Beach (Holmes Beach)](https://images.trvl-media.com/lodging/116000000/115960000/115950900/115950806/5e19eae5.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Cheerful Island Bungalow, Lanai and Walk to Holmes Beach (Holmes Beach)](https://images.trvl-media.com/lodging/116000000/115960000/115950900/115950806/95e1b63c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV - Cheerful Island Bungalow, Lanai and Walk to Holmes Beach (Holmes Beach)](https://images.trvl-media.com/lodging/116000000/115960000/115950900/115950806/5716a4b0.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Cheerful Island Bungalow, Lanai and Walk to Holmes Beach (Holmes Beach)](https://images.trvl-media.com/lodging/116000000/115960000/115950900/115950806/f32e429c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV - Cheerful Island Bungalow, Lanai and Walk to Holmes Beach (Holmes Beach)](https://images.trvl-media.com/lodging/116000000/115960000/115950900/115950806/984f6681.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Cheerful Island Bungalow, Lanai and Walk to Holmes Beach provides laundry facilities and more. Guests can connect to free in-room WiFi. ### Entire home 2 bedrooms2 bathrooms1265 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Air conditioning - Outdoor Space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Cheerful Island Bungalow, Lanai and Walk to Holmes Beach Ob La Di Ob La Da by Anna Maria Island Accommodations 442 62nd St, Holmes Beach, FL 34217 Welcome to Ob La Di Ob La Da by Anna Maria Island Accommodations, a cheerful two-bedroom, two-bathroom ground-level retreat in the heart of Holmes Beach! This cozy bungalow radiates charm and good vibes, just like the iconic Beatles tune “life goes on.” Whether you’re sipping morning coffee on the patio, strolling to the beach, or unwinding in the screened-in lanai, this home is the perfect spot for families or small groups seeking a laid-back Anna Maria Island vacation rental. Highlights • 10-minute walk to Holmes Beach • 2 Bedrooms / 2 Bathrooms • 1 King, 1 Queen, 1 Queen sleeper sofa • Private patio • Screened-in lanai • Washer and dryer • BBQ grill • Quiet residential location near shops and dining • 2 Parking spots Step outside and enjoy the tropical island lifestyle. The private patio is adorned with charming nautical accents and offers the perfect space for a morning coffee or evening BBQ. While you may not see sunsets directly from the patio, you can still soak up the island breezes and end the day with a relaxing meal outdoors. The screened-in lanai provides another inviting space to kick back, enjoy the shade, and embrace the laid-back rhythm of island life. Inside, you'll find a bright, open concept living space with comfortable seating, TV, and thoughtful beachy decor that instantly puts you in vacation mode. The fully equipped kitchen includes modern appliances, and an island bar for casual bites. Enjoy family-style dinners or board games at the dining table, then unwind with a movie or a spontaneous sing-along inspired by the home’s iconic name. The primary bedroom is your restful haven, complete with a king bed and ensuite bathroom with a walk-in shower. The second bedroom offers a cozy queen bed, and there's a queen sleeper sofa in the living room for additional guests. A second full bathroom with a shower/tub combo. Room Details • Primary Bedroom: King bed and ensuite bathroom with walk-in shower • Second Bedroom: Queen bed • Living Room: Queen sleeper sofa This home includes a washer and dryer, BBQ grill, and dedicated parking for two vehicles. You’ll be just a short walk or trolley ride from Holmes Beach, where you’ll find local restaurants, boutiques, and Gulf-front dining. With its central location, Ob La Di Ob La Da makes it easy to explore the island at your own pace. With its fun name, cozy charm, and great Holmes Beach location, Ob La Di Ob La Da by Anna Maria Island Accommodations is the perfect choice for small families or couples looking for a carefree island escape. Book your stay today and remember “Life goes on”! \- This home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. This property does not allow pets of any kind. Bikes are for owner use only. 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Island Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." \*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. ## Property amenities ### Beach - Beach nearby ### Internet - Available in the villa: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Kitchen island - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Hair dryer - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Smart TV ### Outdoor areas - Barbecue grill - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Near a health/beauty spa - Near a hospital - Near an outlet shopping mall - Near the marina - Near the sea ### Things to do - Birdwatching nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Horseback riding nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Parasailing nearby - Sailing nearby - Snorkeling nearby - Surfing/bodyboarding nearby - Swimming nearby - Wildlife walks nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher - Deadbolt lock ### General - Unit size: 1,265 square feet ## Similar properties ![Property grounds](https://images.trvl-media.com/lodging/46000000/45760000/45755000/45754911/cd85e23b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Surf Beach 503 - Spectacular Sunsets - Beach Front Treasure Island - Pool - Hot tub - Kitchen - Washer 9.4 Exceptional 26 reviews CA $252 CA $582 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=45754911&PinnedHotelID=45754911&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/108000000/107410000/107404600/107404501/123c8aa5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Condo with Lanai and Pool, Near AMI Beaches and Marina Bradenton - Pool - Hot tub - Kitchen - Washer 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-06&endDate=2026-01-07&selected=107404501&PinnedHotelID=107404501&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/60000000/59800000/59791600/59791532/7a948148.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Tropical Tiny House Downtown - Pool - Kitchen - Washer - Dryer 10 Exceptional 52 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-06&endDate=2026-01-07&selected=59791532&PinnedHotelID=59791532&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/112000000/111480000/111474800/111474738/5e96b01d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Live the beach life, free amenities, parking, and views! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 1292 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C27.51265%2C-82.71515&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=4MN9ivodJEbq2l_BCllmbECr0SU=) Holmes Beach, FL #### What's nearby - Bradenton Beach \- 9 min walk \- 0.8 km - Island Gallery West \- 11 min walk \- 1.0 km - Holmes Beach Beaches \- 17 min walk \- 1.5 km - Manatee Public Beach \- 2 min drive \- 1.8 km - West Coast Surf Shop \- 3 min drive \- 2.1 km #### Getting around - Sarasota-Bradenton Intl. Airport (SRQ) - 41 min drive #### Restaurants - ‪The Ugly Grouper - ‬6 min walk - ‪Anna Maria Island Beach Cafe - ‬4 min drive - ‪Dunkin' - ‬5 min drive - ‪Skinny's Place - ‬4 min drive - ‪Hurricane Hanks - ‬12 min walk ## Frequently asked questions ### Is Cheerful Island Bungalow, Lanai and Walk to Holmes Beach pet-friendly? ### How much is parking? ### What time is check-in at Cheerful Island Bungalow, Lanai and Walk to Holmes Beach? ### What time is check-out at Cheerful Island Bungalow, Lanai and Walk to Holmes Beach? ### Where is Cheerful Island Bungalow, Lanai and Walk to Holmes Beach located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Cheerful Island Bungalow, Lanai and Walk to Holmes Beach Reviews