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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
Fire Extinguisher
Essentials
Shampoo
Suitable for infants
Shower
Hot water
Extra pillows and blankets
Cooking basics
Beach essentials
Bay
Marina
Toilet
Car not necessary
Dining area
Bird watching
Boating
Paddle boating
Shopping
Water sports
Wildlife viewing
Beach
Near ocean
Boat
Tennis
Cycling
Deepsea fishing
Fishing
Fishing bay
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
Clothing storage
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 |
|---|---|---|---|---|---|
Jun 24 - Jun 26 2025 | $199 | 5 nights | |||
Jun 27 - Jun 27 2025 | $202 | 5 nights | |||
Jun 28 - Jun 29 2025 | $209 | 5 nights | |||
Jun 30 - Jun 30 2025 | $270 | 5 nights | |||
Jul 01 - Jul 01 2025 | $268 | 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 June 24, 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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