Book Direct & Save - No Booking Fees
1679 sq. ft. Cheerful Serenity – Luxury Waterfront Oasis on Perico Bayou with Pool, Dock & Sunset Views
Welcome to Cheerful Serenity, a cheerful 3 bedroom, 2 bathroom waterfront escape with unforgettable sunset views over Perico Bayou. This serene cul-de-sac location feels worlds away yet keeps you close to Anna Maria Island and the Gulf beaches.
Outdoor Oasis
Relax and unwind in the screened lanai with private heated pool and Smart TV, or take in the water views from the hammock, private dock, or secondary seating dock. Bring your boat—there’s a 13,000 lb boat lift and space for a second vessel, and there are no fixed bridges to the Gulf. Wildlife sightings are common here—pelicans, mullet, manatees, and the occasional dolphin. A propane grill makes outdoor entertaining easy.
Designed for Comfort & Gathering
Inside, the home features a warm, open layout with multiple seating areas for meals, games, and movie nights. The kitchen is fully equipped with an induction cooktop and double oven, plus there’s a convenient bar area, laundry, and Smart TVs in every room.
Sleep in Comfort
Primary Suite: King bed + walk-in shower
Guest Bedroom: Queen adjustable vibrating bed
Third Bedroom: Full-over-twin bunk + Xbox for entertainment
Why Guests Love It
Peaceful waterfront location
Private pool + screened outdoor living
Boat lift + Gulf access (no fixed bridges)
Ideal for long stays and family getaways
Close to Anna Maria Island and beaches
Whether you’re boating, grilling, swimming, fishing or watching the sunset, Cheerful Serenity delivers the perfect blend of relaxation and coastal adventure.
24-hour checkin
First aid kit
Fire Extinguisher
Shampoo
Hangers
Laptop Friendly workspace
Suitable for infants
Shower
Dining room
Single level home
Bedroom step free access
Bathroom step free access
Grab rails in shower
Grab rails in toilet
Handheld shower head
Common space step free access
Hot water
Private entrance
Extra pillows and blankets
Cooking basics
Beach essentials
Bay
Marina
Toilet
Car recommended
Books
Games
Video games
Dining area
Ice maker
Antiquing
Bird watching
Boating
Eco tourism
Horseback riding
Water sports
Wildlife viewing
Beach
Downtown
Near ocean
Boat
Golf
Veranda
Long term stays allowed
Deadbolt lock
Hospital nearby
Outdoor lighting
Cycling
Deepsea fishing
Fishing
Fishing bay
Fishing fly
Fishing surf
Golf
Hiking
Jet skiing
Parasailing
Pier fishing
Sailing
Scuba or snorkeling
Water Skiing
Snorkeling
Snorkeling diving
Surfing
Swimming
Wind surfing
Desk chair
Dining table
Outdoor dining
Outdoor furniture
Outdoor sunloungers
Cleaning products
Body soap
Rain Shower
Shower gel
Clothing storage
Drying rack for clothing
Board games
Portable fans
Baking sheet
Barbeque utensils
Coffee
Wine glasses
Hammock
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Sep 12 - Sep 13 2026 | $256 | 4 nights | |||
Sep 13 - Sep 14 2026 | $230 | 4 nights | |||
Sep 14 - Sep 15 2026 | $211 | 4 nights | |||
Sep 15 - Sep 16 2026 | $220 | 4 nights | |||
Sep 16 - Sep 17 2026 | $240 | 4 nights |
Fees:
Last updated on September 12, 2026
Joseph T.We stayed at the property, the home was exactly that, a home! The location was ideal 7 min to Ana Maria Island beaches and restaurants and 5 minutes to town for food shopping and old main street which is full of pubs. The host's hospitality was second to none. We highly recommend Cheerful Rental for your next get away!
Stayed: September 2026 Submitted: September 10, 2026
Andre M.Unforgettable Stay!
Had a wonderful stay. The layout is beautiful, relaxing amenities, thoughtful details throughout the property, made our stay truly relaxing. The location is fantastic. The home is in a wonderful quiet neighborhood —quiet enough to relax, yet close to all the nice local spots located on Anna Maria Island. We loved sitting out to enjoy the beautiful water views and were thrilled to see dolphins right from the property. For boaters, the dock is fantastic and offers quick, easy access to open water. The house is warm, inviting, and meticulously detailed for a comfortable stay.
Stayed: August 2026 Submitted: August 31, 2026
Host response
"This makes us so CHEERFUL! Thank you so much for staying with us!"
Andre M.Unforgettable Anniversary Stay!
My wife and I chose Cheerful Serenity to celebrate our 34th anniversary, and it was a wonderful stay. From the minute we arrived and met Jeff and Sandra, we felt right at home. Since my wife is from Hawaii, walking through the door gave her an instant, comforting sense of being back home. The beautiful layout, relaxing amenities, and thoughtful details throughout the property made our stay truly restful. The location is ideal-nestled in a quiet neighborhood, yet close to all the local spots on Anna Maria Island. As for the home’s private dock, it accommodated our boat perfectly while offering easy access to Tampa Bay and the Gulf. Thank you, Jeff and Sandra Holbrook! We would love to visit again and highly recommend this home to anyone traveling to the area.
Stayed: August 2026 Submitted: August 31, 2026
Host response
"This makes us so CHEERFUL! It was an absolute honor to meet and host you! Hope to have you back soon!"
ShelleyFabulous stay at Serenity, great location, beautiful surroundings and helpful owners. We couldn’t fault it. Positive: Lovely property in a fantastic location. Easy to get around and over to the island, close to amenities and being on the water was just incredible. It was clean and well stocked. We loved the nice touches of providing fishing rods and paddle boards. The surrounding area was quiet and well maintained. Negative: Nothing, we loved it!
Stayed: July 2026 Submitted: August 29, 2026
WellinsonWe had such a blessed and wonderful stay! The neighborhood was peaceful and quiet, with no noise, and the location was great. One of the highlights of our trip was being able to see dolphins and manatees while relaxing and enjoying the yard. It was truly a special experience for our family. We would definitely recommend this place!
Stayed: August 2026 Submitted: August 23, 2026
JuliHouse was great and was spotless upon arrival. Positives: loved the back porch and used the pool daily! The pool was always a perfectly cool temp even with over 100 degree temps! Loved fishing every night off the dock (watch those catfish barbs!). We saw so many animals in water off the dock at night: baby hermit crabs (under dock at night), crabs, stingrays, mullet, more catfish than we could count! Dolphins came to visit almost every morning! Negative: bedroom with bunks should be listed as for small children only and top bunk is very shaky (we were unable to use). Bath towels: get exactly the amount for how many people u say r coming (fyi). Beach towels: bring ur own, theirs r old and tiny. ROAD NOISE: if u want to sit on porch in peaceful silence this is not the house.
Stayed: June 2026 Submitted: June 23, 2026
RebeccaWe truly enjoyed our trip and were certainly CHEERFUL all week. The house is clean, comfortable, and close to everything. The pool was crystal clear, and we enjoyed floating in it every day. Communication with Jeff and the team was easy with fast response times, but we really didn't need anything. Located on a west-facing canal, the sunsets were amazing, and we had daily visits from dolphins and manatees, along with loads of other wildlife to observe. Paddleboarding and kayaking are also so easy right from the house, with miles and miles of shoreline to explore. Fishing right from the dock was also a treat with redfish, snook, and sheepshead easily caught - catfish too, of course. We brought our boat along and found it easy to launch less than a mile away. The boat lift worked great and easily handled our 22' center console. Navigating the channels was simple, as they are very well marked. The highlight for us was the boat lift, easy access to the bay, and fantastic offshore fishing. Combined with the super comfortable accommodations, we can't wait to return!
Stayed: May 2026 Submitted: June 02, 2026
Jacky A.Beautiful waterfront location! Very comfortable older home, very well maintained. Super clean! Wonderfully comfortable both in and outside, but the exterior is A with the huge lanai on the water with boat dock and another sitting area. Amazingly well outfitted home. They provided everything we could ask for in the kitchen. The grill was great. The owners were great - friendly and great communication.
Stayed: February 2026 Submitted: March 13, 2026
Twitter
Email