4.85 ★
Short Term Rental
Anna Maria Island
Cheerful Pelican
- Condominium·6 guests·2 bedrooms·2 bathrooms
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 ...
Amenities
Ocean front
Ocean view
Beach front
Beach view
Waterfront
Heated swimming pool
Available days
Reviews
4.85 (16)·Sebastian·April 2026
Positive: Departamento muy cómodo frente a una playa hermosa. Volveremos a ir
Negative: Nada
·Marty Mates·March 2026
Customer
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.
·Jen·March 2026
Location!
We 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.
·WILLIAM·March 2026
Positive: Great view, close to shops and restaurants, nice pool and hot tub.
Negative: Furniture was a little beat up and there was a ton of traffic.
·Karen·February 2026
Positive: Lovely apartment. Spacious with amazing views and you could walk to the restaurants in Bridge Street
Good to know
House Rules
Check-in: 4 pm
Check-out: 10 am
Pets: not allowed
Smoking inside: not allowed
Cancellation policy
90% refund up to 30 days before arrival
50% refund up to 14 days before arrival
