Enjoy Cheerful coastal living in this beautifully furnished 3-bedroom, 3-bathroom monthly rental in the highly desirable Waterway Condominiums. Ideally located less than 3 miles from the sugar-white sands of Anna Maria Island, this spacious waterfront residence offers the perfect combination of comfort, convenience, and Florida coastal lifestyle.
This fully furnished, turnkey residence features tasteful coastal décor and a comfortable, functional layout designed for extended stays. Sleeping accommodations include a king bed and two queen beds, while a convenient Murphy bed provides additional sleeping flexibility. Upstairs bonus rooms offer valuable extra space that can be used as a home office, reading room, or additional living area.
The main living space features soaring vaulted ceilings and plenty of comfortable seating for relaxing or entertaining, along with a dining table and bar seating. A large picture window provides an incredible view of the surrounding canal and Palma Sola Bay, bringing the beauty of the waterfront indoors. Thoughtful touches throughout, including custom closets, a wash basin in the laundry room, and neutral coastal décor, make this an inviting place to settle in and enjoy an extended stay.
Step outside and embrace the waterfront lifestyle with a deeded boat slip featuring a true boat lift capable of accommodating a boat up to 26 feet. This is an exceptional amenity for boating enthusiasts, offering the opportunity to keep your boat right at home and enjoy easy access to the area's waterways, strong local fishery, sandbars, island excursions, and waterfront restaurants. The surrounding canals and Palma Sola Bay are also home to abundant wildlife, including frequent manatee and bird sightings.
Waterway offers an impressive selection of amenities, including a fitness room, clubhouse, billiards, ping pong, and tennis courts. The convenient location puts you close to local restaurants, shopping, parks, and everyday necessities, while Anna Maria Island and its beautiful Gulf beaches are just minutes away.
Whether you're escaping the cold, relocating to the area, working remotely, or simply looking for an extended Florida getaway, this turnkey monthly rental offers a comfortable home base for experiencing the very best of the Gulf Coast. Come relax, explore, and enjoy the Cheerful lifestyle!
30 DAY MINIMUM STAY - PLEASE CALL FOR LONGER TERM DISCOUNTS OR ANY QUESTIONS!
*All bookings are subject to HOA approval that will include background checks. Minimum of 15 days advance notice for booking.
24-hour checkin
First aid kit
Fire Extinguisher
Hangers
Suitable for infants
Shower
Dining room
Hot water
Private entrance
Extra pillows and blankets
Cooking basics
Beach essentials
Bay
Marina
Toilet
Car necessary
Books
Games
Dining area
Ice maker
Bird watching
Horseback riding
Water sports
Wildlife viewing
Beach
Near ocean
Boat
Tennis
Long term stays allowed
Outdoor lighting
Deepsea fishing
Fishing
Fishing bay
Fishing fly
Fishing surf
Parasailing
Pier fishing
Sailing
Scuba or snorkeling
Snorkeling
Snorkeling diving
Swimming
Wind surfing
Contactless Check-In/Out
Dining table
Communal tennis court
Outdoor dining
Outdoor furniture
Outdoor sunloungers
Clothing storage
Exercise equipment
Board games
Baking sheet
Barbeque utensils
Coffee
Trash Compactor
Wine glasses
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 10 - Dec 20 2026 | $130 | 30 nights | |||
Dec 21 - Dec 31 2026 | $190 | 30 nights | |||
Jan 01 - Jan 31 2027 | $190 | 65 nights | |||
Feb 01 - Mar 15 2027 | $200 | 65 nights | |||
Mar 16 - Mar 31 2027 | $200 | 30 nights |
Fees: