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1076 sq. ft. Welcome to The Cheerful Pelican – Your Perfect Beach-to-Bay Getaway!
Discover the ultimate escape in this charming 2-bedroom, 2-bathroom retreat, perfectly nestled between the stunning Gulf beaches and tranquil bay waters. The Cheerful Pelican offers the best of both worlds with sunrise views over the bay and breathtaking sunsets over the Gulf, all enjoyed from two screened lanais just steps from the sand and pier.
Conveniently located between vibrant Bridge Street and serene Coquina Beach, this delightful condo places you at the heart of island life. Step outside to find a trolley stop and a Gulf Drive walkway ready to take you on your next adventure. Whether you’re soaking up the sun on the beach, strolling along the pier, or exploring nearby shops and restaurants, paradise truly begins here.
The quaint, 16-unit condo complex offers a laid-back atmosphere with an array of amenities designed for relaxation and recreation. Dive into the pool, unwind in the spa, or challenge your friends to a match of tennis or pickleball. Bring your fishing gear and take advantage of the pier or grills for a fresh-caught feast.
24-hour checkin
First aid kit
Fire Extinguisher
Essentials
Shampoo
Hangers
Suitable for infants
Shower
Hot water
Extra pillows and blankets
Cooking basics
Beach essentials
Room darkening shades
Bay
Marina
Toilet
Car not necessary
Dining area
Ice maker
Bird watching
Boating
Paddle boating
Shopping
Water sports
Wildlife viewing
Beach
Near ocean
Boat
Tennis
Long term stays allowed
Cycling
Deepsea fishing
Fishing
Fishing bay
Fishing fly
Fishing surf
Hiking
Jet skiing
Parasailing
Pier fishing
Sailing
Scuba or snorkeling
Snorkeling
Snorkeling diving
Surfing
Swimming
Wind surfing
Dining table
Communal tennis court
Outdoor dining
Outdoor furniture
Outdoor sunloungers
Body soap
Shower gel
Clothing storage
Board games
Baking sheet
Barbeque utensils
Coffee
Wine glasses
No Booking or Service Fees
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Apr 02 - Apr 03 2026 | $431 | 3 nights | |||
Apr 03 - Apr 04 2026 | $434 | 3 nights | |||
Apr 04 - Apr 05 2026 | $400 | 3 nights | |||
Apr 05 - Apr 06 2026 | $443 | 5 nights | |||
Apr 06 - Apr 07 2026 | $432 | 5 nights |
Fees:
Notes:
House Rules
Check-in: 4 pm
Check-out: 10 am
Children: allowed
Infants: allowed
Pets: not allowed
Parties and events: not allowed
Smoking inside: not allowed
Cancellation Policy
100% refund up to 30 days before arrival
50% refund up to 14 days before arrival
Last updated on April 02, 2026
Marty M.We spent spring break at the Cheerful Pelican and had an absolutely wonderful week. The condo was spotless, comfortable, and thoughtfully stocked, with great views and an easy walk to the beach. Everything worked perfectly, and the space felt welcoming from the moment we arrived. Jeff and Shandra Holbrook at Cheerful Rentals were fantastic—friendly, responsive, and genuinely helpful before and during our stay. Check-in was seamless, communication was clear, and they truly cared about our experience. This was the kind of relaxing, stress-free vacation every family hopes for. We would gladly return and highly recommend Cheerful Pelican and Cheerful Rentals.
Stayed: March 2026 Submitted: March 30, 2026
JenWe loved the location at Cheerful Pelican. It was absolutely the best! The view from the balcony was amazing! We loved being able to walk down the steps and across the street right to the beach. So many wonderful sunsets. The pool and hot tub were a perfect retreat after an afternoon in the sun. Access to the bay was a nice plus too, though it didn't impact us a whole lot. We brought pickle ball paddles and had a great time on the court on property. The place is well taken care of, and the unit was very clean. Everything was just as advertised and Jeff was very responsive to any questions, even allowing us to check in early! The trolly stop is right across the street, but we ended up driving to a few places on the northern part of the island. There are a lot of great restaurants on the island, and the Market Street area is within walking distance of the rental. Definitely a great place to stay if on AMI! Would recommend to anyone.
Stayed: March 2026 Submitted: March 29, 2026
Jen H.It's all about the location!
We loved our time at Cheerful Pelican! We were looking at a place with a Gulf view, easy access to the beach, and also a hot tub and heated pool. This place had it all! We loved how we could watch the sunrises and sunsets as there are patios to the west and east in this rental. There were some beach chairs and boogie boards to use for our kids. The beach across the street was amazing. Parking was covered, and the pickle ball courts were a bonus for us. Would definitely recommend this place!
Stayed: March 2026 Submitted: March 21, 2026
Host response
"This makes us so CHEERFUL!!! Thank you so much for staying with us, and we hope to have you back soon!"
DavePositive: Loved sitting on the screened in deck facing the ocean at night and just listening to the waves. The sunsets were gorgeous from the living room. The apartment was super cute decorated and made the stay feel fun. Great location to everything. We walked the few blocks to a street festival one night that was super fun with very friendly people. The pool and hot tub were relaxing and clean. Loved, Loved, Loved having decks and doors on both sides of the apartment. We were able to open everything wide and it actually made the place feel even bigger. Negative: The apartment was very clean, except for the floors. They looked clean to the eye, swept well, but they had not been actually mopped in a while and everyone's socks were toast.
Stayed: October 2025 Submitted: December 19, 2025
Lisa D.Perfect rental
I came down with my 87 year old mom and sister. The unit was so clean and inviting. Had everything we needed for our stay. Love the porch facing the bay, and such a quick walk to the beach. My sister and I walked to Bridge Street a few times to shop and eat. We would definitely stay here again. The owners are great to work with and are only a few blocks away if you need anything!
Stayed: October 2025 Submitted: November 03, 2025
Host response
"This makes us so CHEERFUL!!! So great meeting you all! Hope to have you back soon!"
BrookeThis location was an EXCELLENT stay for our 5 nights on AMI! The location is excellent being just across the street from the beach, allowing for quick trips in and out as needed. Also, sitting on the screened in lanai's facing BOTH the gulf or the bay was a special treat. The amenities were fantastic. The condo came with everything we would need including swim towels and a full kitchen of cookware. Bedrooms were very comfortable and great for families with kids to have their own room. The pool and hot tub out back was a great addition for night swims! A lot of personal care has gone into seeing that this condo is aesthetically personalized and a very nice vacation home. And finally, communication was AMAZING. We received several "get ready for" emails, with very clear instructions on how to access the condo AND how to reach someone should there be any concerns. It felt like staying at a familiar friend's house for the week! Highly recommended (and we have stayed at several locations on the island - this is one of the best!)
Stayed: July 2025 Submitted: July 14, 2025
ReneeWe have travelled to Anna Maria Island many times and the Cheerful Pelican is located in the perfect spot-directly across the street from the beach. Screened in patio is the perfect location to watch the sunset or sunrise. It's just a short walk to Bridge Street, where there are plenty of places to eat or shop. Even though we didn't cook much we had everything available in the kitchen to make some simple meals. Washer and dryer came in handy, we were able to wash all our clothes before heading back home. We has one small issue that was quickly fixed by Jeff within 30 minutes. We would not hesitate to rent the Cheerful Pelican again.
Stayed: May 2025 Submitted: May 21, 2025
Carrie MurphyWe loved our stay at Cheerful Pelican and hope to be back soon! Positive: The location is great — we were at the beach in under 2 minutes! It seemed to be a pretty quiet stretch of the beach, too. We always had plenty of space to ourselves and really enjoyed the provided beach chairs, towels, and sand toys. We also loved the pool and hot tub! The condo has balconies that overlook both the pool/bayside and the Gulf, which was really nice, too. Everything was clean in our unit and we loved having a full kitchen, washer and dryer, and two bathrooms. It was very functional for our family of 5. Beds were super comfy, too! There’s a trolley stop that drops off right across the street and another stop a short walk away to get to Holmes Beach and Anna Maria. We mostly stayed near the condo, but it was nice to take the trolley around the island and not have to worry about parking. Jeff was a wonderful host, too! He was always friendly, responsive, and helpful. We wouldn’t hesitate to stay again!
Stayed: March 2025 Submitted: April 02, 2025
LucyWe had a wonderful stay at the Pelican. They provided everything we needed to set up for a few days. From the balcony on the Gulf side you could see the sunset every evening. The beach is beautiful. We were able to walk to Bridge Street to enjoy the shopping and restaurants everyday. Would highly recommend this condo at the Cheerful Pelican. Our contact Jeff Holbrook was wonderful and provided everything we needed and answered any questions. Thank you,
Stayed: March 2025 Submitted: March 12, 2025
Jim S.Cheerful Pelican was great!
We stayed for 3 weeks, great location across from the beach, and walking distance to Bridge street. The layout of this condo has 2 patios, one in bedroom facing east watching sunrise, and the 2nd in living room facing west, the beach and the sunset each evening. Our host Jeff was amazing , answering questions very promptly and always available. Unit was clean and spacious. We also appreciated the in unit laundry, and parking was shaded for the vehicle. The island is still recovering at this time ( Jan/Feb 2025) but this complex had everything up and running and the stay was quiet and peaceful. We stayed at Siesta Key last year, wife and I both agree that we would stay here again before going back to Siesta Key.
Stayed: January 2025 Submitted: February 10, 2025
Host response
"This makes us so CHEERFUL!!! Jim's group were fantastic, and we hope to have them back soon!"
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