IT'S A GREAT DAY AT THE CHEERFUL COAST!

Welcome to Cheerful Rentals!

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Our top properties

- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
Breathe Inn - Entire Duplex
- 14 guests
- 5 bedrooms
- 4 bathrooms
- Heated swimming pool
- Swimming pool
- Beach essentials
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
Coquina Cheer on Anna Maria Isl.
- 4 guests
- 1 bedroom
- 1 bathroom
- Heated swimming pool
- Swimming pool
- Beach essentials
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
- Short Term RentalAnna Maria Island
  4.90 ★
Coastal Cheer on Anna Maria Isl.
- 4 guests
- 1 bedroom
- 1 bathroom
- Heated swimming pool
- Swimming pool
- Beach essentials
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
Bay View Cheer
- 4 guests
- 2 bedrooms
- 2 bathrooms
- Heated swimming pool
- Swimming pool
- Beach essentials
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
B and B's Boatshed
- 4 guests
- 2 bedrooms
- 2 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
Intracoastal Connections
- 6 guests
- 3 bedrooms
- 3 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
- Short Term RentalPerico Island-Anna Maria Sound
  5.00 ★
Kingfisher Cay
- 8 guests
- 3 bedrooms
- 3 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
- Monthly MinimumNear IMG Academy
  5.00 ★
Mahi Manor
- 4 guests
- 2 bedrooms
- 2 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
- Short Term RentalAnna Maria Island
  4.95 ★
Cheerful Pelican
- 6 guests
- 2 bedrooms
- 2 bathrooms
- Ocean front
- Ocean view
- Beach front
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
- Short Term RentalAnna Maria Island
  5.00 ★
Cheerful Oasis
- 6 guests
- 2 bedrooms
- 2 bathrooms
- Ocean front
- Beach front
- Waterfront
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
- Monthly MinimumAnna Maria Island
Martinique Cheer
- 4 guests
- 2 bedrooms
- 2 bathrooms
- Ocean front
- Ocean view
- Beach front
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
- Monthly MinimumLongboat Key
Bay Dream Believer
- 5 guests
- 2 bedrooms
- 2 bathrooms
- Ocean view
- Waterfront
- Heated swimming pool
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
Waterway Cheer
- 4 guests
- 2 bedrooms
- 2 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
- Monthly MinimumNear IMG Academy
Bay View Sunset
- 6 guests
- 3 bedrooms
- 3 bathrooms
- Waterfront
- Heated swimming pool
- Swimming pool
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
- Short Term RentalPerico Island-Anna Maria Sound
Cheerful Serenity
- 8 guests
- 3 bedrooms
- 2 bathrooms
- Waterfront
- Swimming pool
- Beach essentials

Please Call 941-32-CHEER to discuss Monthly Rates