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! Sunset Bliss! $6000 in Feb 2020!

Indulge in endless water views from this spacious second story Gulf front condo! Elevator, 3 bedrooms, beach side sitting area and views from almost every room make this a fantastic island getaway! Don’t miss the introductory special for Feb 2020! Only $6000 rental fee. 28 night minimum.

Call 941-779-0304 or book Sunset Bliss online! 



Last Minute Duncan DealChristmas Week Specials!

Take advantage of reduced rates for the week of 12/21 – 12/28/2019 and enjoy time with the family island style!

West O’ Gulf, 4 bedrooms:  $4000   NOW $3500 rental fee!
Seagrass Retreat, 5 bedrooms: $3540  NOW $3000 rental fee!
Blue Coconut Bungalow, Sea Mist 3 bedrooms: NOW $2350 rental fee!

Call or book online!

15% OFF December 2019

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

Call or book Sunkissed online!




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!

Stay 4 weeks in January 2020 at Cayman Cay 201 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!


Duncan Vacation Rental Pleasant Palms$100/night January 2020 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 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!


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.