Book Direct & Save - No Booking Fees
603 sq. ft. This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay!
Coastal amenities: front screened lanai, heated pool, beach toy closet (including chairs), pull-out sofa, WIFI, 2 Roku TVs, full kitchen supplies, washer/dryer, dishwasher, tub for the kiddos
The condo, unit 14, is on the second floor, so be ready for some steps! You'll love the view from the lanai. While we can't really call it an ocean view, you can see the water and an occasional boat passing by!
You'll be all alone in the condo with pool access and a storage room with beach chairs, toys, shades and an umbrella.
We live right down the street (within 3 miles) and are here to help you! Our real estate store front is located at 119 Bridge Street, just steps away from the unit. Please come see us!
Quiet, 16 unit condo complex steps away from Bridge Street's action!
We have 1 parking space. Once you arrive, there's plenty to do within walking distance and a free shuttle on the entire island.
24-hour checkin
First aid kit
Fire Extinguisher
Essentials
Shampoo
Hangers
Suitable for infants
Electric kettle
Shower
Hot water
Extra pillows and blankets
Cooking basics
Beach essentials
Room darkening shades
Bay
Marina
Toilet
Car not necessary
Books
Dining area
Bird watching
Boating
Eco tourism
Horseback riding
Paddle boating
Shopping
Water sports
Wildlife viewing
Beach
Near ocean
Boat
Luggage dropoff allowed
Long term stays allowed
Outdoor lighting
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
Outdoor dining
Outdoor furniture
Outdoor sunloungers
Cleaning products
Body soap
Conditioner
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 |
|---|---|---|---|---|---|
Dec 04 - Dec 05 2025 | $131 | 3 nights | |||
Dec 05 - Dec 06 2025 | $196 | 3 nights | |||
Dec 06 - Dec 07 2025 | $209 | 3 nights | |||
Dec 07 - Dec 08 2025 | $170 | 3 nights | |||
Dec 08 - Dec 09 2025 | $160 | 3 nights |
Fees:
Last updated on December 04, 2025
LaurieThe location of the unit was perfect, with just a short distance walk to the beach or the bay. Very close to historical Bridge Street, which has lots of restaurants and fun shops. The unit itself was very clean and had everything necessary for our stay. One of the best features I found was that Jeff was extremely helpful in regards to all our needs, and very accommodating during our stay. Would definitely stay again. Laurie
Stayed: October 2025 Submitted: October 24, 2025
DavidThis spot is the perfect location on the island! Walking distance to restaurants, gulf and bay and you can see water from both sides of the condo! The pool is great and the vibe of the place and proprietor is even greater. We will be back.
Stayed: October 2025 Submitted: October 10, 2025
VeronicaTan lindo y cozy volvería 1000 veces! Positive: El apartamento es muy cómodo, está equipado excelentemente tiene de todo para playa, hasta un carrito!! Y Lavarropas/secarropas la cocina tiene todo también! Negative: Todo nos gustó!
Stayed: September 2025 Submitted: October 07, 2025
IrisDer Aufenthalt war perfekt mit dieser Wohnung. Wir durften auch schon früher rein und am Abreise Tag länger bleiben, was Positive: Die Lage war super. Der Pool war sehr angenehm. Die Wohnung war sehr liebevoll eingerichtet. Und wenn man Fragen hatte bekamen wir sehr schnell Antworten. Negative: Alles war gut.
Stayed: October 2025 Submitted: October 07, 2025
BenCan’t wait to go back!! Positive: The property was perfect for the two of us but four people could comfortably stay here as well. The hosts, Jeff and Shandra were so professional as well as personable. Had the pleasure of getting to meet Jeff as their office is only a couple of blocks away on Bridge Street. We felt if there had been any issues they would have been resolved very quickly. This location is perfect because it is only a block to the beach and two blocks to Bridge Street. It’s just a short drive back across the bridge to Cortez where some amazing seafood places are located as well. All in all we had a wonderful experience.
Stayed: June 2025 Submitted: July 16, 2025
BrandonA fabulous time with our family. Positive: this location was FANTASTIC! We loved the accessibility to the shops, also the accessibility to the beach. It was such a relaxing week, lots of beach time! We stayed with our family of four, and we had plenty of room. Thank you for our wonderful stay, we would love to be back one day. Negative: Place needs some updating.
Stayed: June 2025 Submitted: June 14, 2025
JeffOur recent visit to Anna Maria Island was absolutely delightful. We can't thank Cheerfull Vacation Rentals enough for their help and support. Thank You Jeff and Chondra for a smooth process of selecting a property for rental. Exceptional communication and Correspondence making the process flawless. We would definitely recommend your services in the future for visiting this Florida area.Cheerfully,Kim and Jeff
Stayed: May 2025 Submitted: May 17, 2025
PeterGreat place to stay. Positive: lovely, comfortable apartment with friendly and helpful owners. we particularly appreciated the use of the beach chairs and umbrellas etc and the buggy to take them to the beach Negative: nothing
Stayed: April 2025 Submitted: May 02, 2025
Alli SerughettiCome a casa Positive: Appartamento con tutto l'indispensabile e di più. Posizione comoda a duecento metri dalla spiaggia. Ambiente confortevole e pulito anche se un po' "casa dei nonni al mare". Ci torneremo sicuramente!!! Negative: Nulla
Stayed: March 2025 Submitted: April 01, 2025
PetraWe loved staying at the cute little condo. It had everything we needed. It was nice and clean. Booking was easy and Jeff answered every email straight away. We met Jeff and Shandra personally and they were very friendly and helpful.Der Aufenthalt in der kleinen süssen Wohnung hat uns sehr gut gefallen. Es war sehr sauber und hat alles was man braucht. Buchung online war einfach und Jeff beantwortete meine e-mails immer sehr freundlich und sofort. Wir haben Jeff und Shandra auch persönlich getroffen. Sie waren sehr freundlich und hilfsbereit. Petra, Januar 2025
Stayed: January 2025 Submitted: January 11, 2025
MorganWe will be back! It was our first time traveling as a family with our 1 year old. We were nervous at first, but our stay was amazing and very memorable. It was extremely clean, and the location was perfect. We loved using the beach equipment offered by our host. It is a must stay!
Stayed: December 2024 Submitted: January 01, 2025
Jurgen ChristineWe loved this cozy retreat in a quaint beach town! Positive: A beautiful place in the perfect little beach town! I stayed here with my two teenage daughters for a tournament and we had an amazing time! The adorable apartment was so clean (which is so important to me;)) and the owners couldn't have been more accommodating. The pool area was an added bonus with the short walk to the beach, shops and restaurants. We will definitely stay there again. We absolutely loved it!!
Stayed: November 2024 Submitted: November 25, 2024
LisaBy far, the best location on the island. Short walk to restaurants, beach, piers, Bridge Street and pickle ball court. The owners were very helpful and were flexible with our check in. Great communication. The condo had everything we needed - which is so helpful. It came with beach towels, chairs, beach toys and even a wagon to pull it all. We also spent time at the condo pool. The pool was clean and had lots of tables and chairs for us to use. No issues with parking either. We will definitely rent again.
Stayed: July 2024 Submitted: August 05, 2024
MatthewThere were some maintenance issues during my stay, which would normally justify a one-star review. However, the owner was incredibly accommodating and did everything in his power to make sure we were still comfortable in the unit. He answered every call and communicated very thoroughly every step of the way, and earned every bit of a 5 star review. I would have no reservations coming back again. Great pool and accommodations, and could not ask for a better location on the island.
Stayed: June 2024 Submitted: June 12, 2024
Arianna C.I recently stayed at this stunning beach apartment and had an absolutely amazing experience. From the moment I arrived, everything exceeded my expectations. the apartment offers easy access to the sand and sea, perfect for morning walks and evening sunsets. The neighborhood is vibrant and friendly, with a variety of restaurants, cafes, and shops within walking distance. It’s also conveniently close to local attractions and recreational activities, making it an ideal spot for both relaxation and adventure.The service provided by the management team was outstanding. From the seamless check-in process to their attentiveness throughout my stay, I felt truly taken care of. Any questions I had were promptly answered, and they went above and beyond to ensure I had everything I needed for a perfect stay. I highly recommend this beach apartment to anyone looking for a luxurious and hassle-free beach getaway. Everything was amazing, and the service was top-notch. I would definitely stay here again and rate this property 5 out of 5 stars.
Stayed: May 2024 Submitted: May 27, 2024
TimothyIt was very relaxing. The host Jeff was very attentive to all our needs Positive: ,We loved the location and everything was so easy to get too. The neighbors were very nice and welcoming. We would like to revisit for sure. The weather was absolutely beautiful. Thank you Negative: nothing , it was nice
Stayed: May 2024 Submitted: May 18, 2024
BRENDACoastal Cheer BLISS!!! Positive: Spectacular! From first contact to check out these guys provide above and beyond customer service and attention to detail. One of the owners came to the condo site to greet me and make sure I got in and that everything was up to par. The apt was SPOTLESS. A welcome basket of healthy snacks, coffee, creamers on counter, nice shampoo conditioner soap lotion etc , high end towels and sheets and pillows and comforters and the bed was memory foam and SO comfortable to lay there n watch the sun come up. The linai deck looks over the pool. Out of all the places, 7 total I've stayed on Anna Maria this place took the cake and stood out in above the rest in every way. Even checking in to see if I was comfortable or needed anything, a wonderful book about their family and just a whole amazing vibe these guys have. I couldn't recommend staying in one of their u it's enough. Oh AND like that wasn't enough the price couldn't be beat. Plus your a quick walk to beach and bridge st. Thanks coastal cheer! Stay awesome! Negative: 3rd floor and no elevator.
Stayed: May 2024 Submitted: May 08, 2024
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