Anna Maria Island Vacation Rentals - Duncan Real Estate

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Real Estate Sales

Anna Maria Island is the place to be and Duncan Real Estate will find you the perfect property.

Want to know what your home is worth? Your selling process with Team Duncan starts here.

Vacation Rentals

Make the memories of a lifetime. Find the perfect property to relax and enjoy the Florida lifestyle.

Our local team of vacation rental specialists is happy to assist you booking the perfect beach getaway.

Rental Management

Duncan Real Estate provides comprehensive, year round property management services for home owners.

Our dedicated team will offer total peace of mind when you’re away from your island home or investment property.



Since 2001 Duncan Real Estate has exceeded your expectations and provides most current, objective and comprehensive information for all your real estate needs. If you are ready to buy or sell island property or looking for a relaxing Anna Maria Island vacation: Experience the Duncan Difference! We do business the way it was meant to be – friendly, trustworthy and with your best interests in mind.

Vacation Rental Properties

Enjoy the sunset side of Florida with a Duncan Real Estate Vacation Rental on beautiful Anna Maria Island! Our local team of vacation rental specialists is happy to assist you finding the perfect beach getaway. Begin your search with always accurate availability or contact us to start the reservation process.

Vacation Specials

*NEW! Blue Coconut Bungalow

Fabulous new vacation home with pool and spa oasis and no streets to cross to the beach! Seasonal dates 2020 are available! Don’t miss out on this great tropical island getaway!

Call or book Blue Coconut Bungalow online now!


SAVE $250 October 2019 Special!

Book these selected properties and save $250 off the rental fee for any October 2019 arrival:
Island Priva-Sea, 3 bedroom, private pool, canal front, North end
Lazy Hammock, 3 bedroom, private pool/spa, canal front, North end
AMI Beach Home, 4 bedroom, private pool, very close to beach
Pier to Pier Paradise, 4 bedroom, private pool, Tampa Bay views
Seagrass Retreat, 5 bedroom, private pool


15% OFF November and December 2019

Book a week at Sunkissed in November and December 2019  and enjoy this 3/2.5 BD/BA home with private pool at 15% OFF the rental fee! Thanksgiving week included!

Call or book Sunkissed online!



Duncan Vacation Rental Pleasant PalmsDec 2019 – January 2020 $100/night Special!

Stay at Pleasant Palms for $100 rental fee per night and 50% off the pool heat. 3 bedrooms, screened in lanai, private pool. Even comes with a beach and 2 bikes. Call for availability.

Call to book Pleasant Palms now!



Stay 1 week for free at Cayman Cay 107!

Book 21 nights in Dec 2019, June or July 2020 and add one additional week for free!
This lovely, ground level 2/2 condo is just a short block from the beach and has a shared pool.

Call to book Cayman Cay 107 now!


Canario Cottage PoolYear End 20% OFF Special!

Stay any week in 2019 at Canario Cottage and save 20% off the rental fee! This 3/3 elevated home with private pool is in a great North end location. New master bathroom! Enjoy the bay or Gulf side beaches and be within minutes of all the shops and eateries along historic Pine Ave!

Call or book Canario Cottage online!


Save $250 for Jan 2020 at Cayman Cay 201!

Stay 4 weeks in January 2020 and save $250 for a rental fee of $3750! This 2/2 condo is beautifully updated and located just across the street from the white sandy beaches of Anna Maria Island! This spacious second floor rental invites to a Enjoy a fantastic beach vacation in this spacious second floor with covered parking and a heated pool in the complex.

Book now!


Last Minute Duncan DealLast minute Specials!

Select properties offer a Last Minute Deal for any October 2019 arrival. Take 10% off the rental fee!
(New reservations only, discounts don’t stack).

Call or book online!



This image has an empty alt attribute; its file name is sunshine2.jpgShort Stay Specials!

Just staying a few nights?
Search here for 3+ nights through December 20th, 2019!

Click here for all Duncan Deals!



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Properties for Sale

Duncan Real Estate is the foremost expert for buying and selling real estate on Anna Maria Island and throughout Manatee County. If you are searching for a home on or near the white sand beaches of the Gulf of Mexico or looking to sell our team of dedicated real estate professionals is ready to meet your every Anna Maria Island real estate need. Discover the Duncan difference and stop by at our office at 310 Pine Avenue, Anna Maria or email us with your real estate questions.

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Contact us or call Duncan Real Estate today at 941-779-0304 to speak with our knowledgeable real estate specialists.