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Anna Maria Island 5+ Bedroom Vacation Rentals

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Anna Maria Island is the premier beach vacation location in Florida. Situated on the beautiful Gulf Coast, Anna Maria Island has so much to offer. Gorgeous beaches, great restaurants, and a never ending list of activities are all part of a great vacation here. Anna Maria Vacations has the best selection of vacation rentals to add to a memorable visit.

With some of the best coastline near or far, enjoy the simplicity of this pristine landscape and all of the coastal amenities that accompany this popular vacation destination.

Anna Maria Island is a great place for family vacations, weddings, a fun weekend with a group of friends and so much more. Here on this page you will find our rental homes with 5 or more bedrooms. These rental homes are perfect for multi family vacations as well. We have homes that have enough space for everyone.

These homes can accommodate up to 20 guests.

Anna Maria Island has vacation rentals that have five or more bedrooms that can accommodate up to 20 people. This is a great choice if you want to split the rental price among everyone. Situated on the beautiful Gulf Coast, Anna Maria Island vacation rentals have so much to offer.
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Absolute Paradise
From $2450 to $7700 per week
  • Brand new construction
  • 5 bedrooms, 4 bathrooms
  • Private heated pool with spa (blower feature is disabled)
  • 4 Kings, 1 twin over full bunk bed, 2 Sleeper Sofas
  • Sleeps up to 13
  • Rooftop deck with beautiful views
  • Short 2 minute stroll to the Gulf
  • Close to local restaurants and shops-Ginny's and Jane's Bakery and Pine Avenue
  • 8 TV's, DVD Player, Xbox gaming system, Air Hockey
  • Ping Pong and Foosball table, Corn Hole, Darts and board games
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Harbor Side
From $1750 to $7000 per week
  • On our Professional Linen Service Program
  • Private, ground level, canal front home
  • 5 bedrooms and 3.5 bathrooms, sleeps 14 in beds
  • Beautiful canal and Bay views
  • Private heated pool and boat dock
  • Just a short 2 minute stroll to the Gulf beach
  • Flat screen TV's and wireless internet
  • Washer and dryer
  • Fully equipped kitchen with new stainless steel appliances
Book now
Montego Bay
From $2450 to $7000 per week
  • On our Professional Linen Service Program
  • Brand new construction elevated luxury property
  • 5 bedrooms and a den, 4 full bathrooms
  • Rooftop deck with beautiful views of the Island and the Gulf
  • Private heated pool with spa, covered lanai, BBQ grill, tropical landscaping, 6 bikes and 2 beach carts
  • 4 Kings, 1 Bunk bed (Twin over Double)-Sleeps up to 11
  • Just a short 2 minute stroll to the Gulf Beaches
  • Close to local restaurants and shops and Pine Avenue
  • Poolside TV, Xbox gaming system, Wireless Internet and more
Book now
Beach Haven
From $2800 to $13202 per week
  • This home is enrolled in our Professional Linen Program
  • 8 bedrooms and 7.5 bathrooms-New construction luxury home
  • 7 King beds, 2 sets of bunk beds, 1 sleeper sofa-Sleeps up to 20
  • Rooftop deck with hot tub and amazing Gulf and Bay water views
  • Deluxe private heated pool with a water slide, spa and a swim-up Tiki table
  • Just a short 3 minute stroll to the Gulf beach- short walk to restaurants and shopping
  • Fully stocked kitchen with brand new stainless steel appliances
  • Wireless Internet, Flat Screen TV's throughout, Xbox gaming system
  • Pool table, Foosball table and many other amenities
  • Pool side covered lanai, gas BBQ grill and tropical landscaping
Book now
Bermuda Bay
From $2450 to $7000 per week
  • On our Professional Linen Service Program
  • Brand new construction
  • 5 bedrooms, 4 bathrooms
  • Rooftop deck with beautiful views
  • Private heated pool with spa
  • Xbox gaming system, stand up Classic Arcade game, Pool and Foosball table
  • 4 Kings, 2 sets of bunk beds, 1 sleeper sofa-Sleeps up to 14
  • Just a short 5 minute stroll to the Gulf-Bikes, beach wagon and toys available
  • Close to local restaurants and shops- Pine Avenue
  • Dog friendly property for an extra fee
Book now
Emerald Seas
From $1750 to $7000 per week
  • On our Professional Linen Service Program
  • Newly renovated-5 bedrooms and 4 bathrooms
  • Private heated pool with spa
  • Less than a 5 minute walk to Gulf beaches
  • Close to Bean Point Beach
  • 1 King, 2 Queens, 5 Twins, 1 Full and 1 Bunk bed-Sleeps 14
  • 10 beach chairs available for guest use
  • 6 TVs, 4 DVD players, Wii gaming system
  • Pool side bar, screened in porches, Foosball table
  • Dog friendly property for an extra fee
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Serenity Beach
From $4200 to $11200 per week
  • On our Professional Linen Service Program
  • Brand new luxury 5 bed plus a den and 4.5 bath construction
  • 4 King beds, 3 Twins, 1 trundle bed- comfortably sleeps up to 13
  • Tropical private heated pool with spa, foosball, ping pong tables
  • Just a short 5 minute walk to the beautiful Gulf beaches
  • Located on a canal-short distance to open water access
  • Fully stocked kitchen with brand new stainless steel appliances
  • Walking distance to Island shops and restaurants-Pine Avenue
  • Covered patio-gas BBQ grill, outdoor living space, dock
  • 2 living areas-one on each living level
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Cabana Beach
From $2100 to $6300 per week
  • On our Professional Linen Service Program
  • New luxury construction - 3200 sq feet of living space
  • Private, heated salt water pool with spa
  • Foosball table available for guest use as well as 4 bikes, beach chairs, toys and wagon
  • Large covered pool-side lanai
  • 3 King beds, 1 Queen bed, 2 Twins and 2 sets of bunks
  • Only a 2 minute stroll to the fantastic Gulf beaches
  • High end furniture, furnishings and decor
  • 8 HD flat screen TVs, wireless internet
  • Spacious bedrooms, lots of room
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Summer House
From $2800 to $13202 per week
  • On our Professional Linen Service Program
  • New 8 bedroom and 6 bathroom luxury private home- 3,400 sq ft.
  • Rooftop deck with hot tub and amazing Gulf and Bay water views
  • Just a short 2 minute walk to the beach
  • 6 Kings, 4 Twins (bunk beds) and 1 twin over full bunk bed-sleeps 19 in beds
  • Fully stocked kitchen with new stainless steel appliances-2 sets of washers and dryers
  • Walking distance to Island shops and restaurants
  • Wireless Internet, Flat Screen TV's, X-Box gaming system, Pac Man/Galaga video game
  • Private heated pool with water slide, spa and a swim-up Tiki table, pool-side lanai with bar, TV, Ping-Pong, Foosball and a Pool table
  • Dog friendly property for an extra fee
Book now
Direct Beach View
From $2947 to $10997 per week
  • On our Professional Linen Service Program
  • Brand new luxury 5 bedroom and 4.5 bathroom
  • Directly across the street from the beach
  • Private heated pool with spa
  • Multiple covered decks
  • 4 Kings and 2 Twins-Sleeps 10
  • Only 2 houses away from the beach access
  • TV in every room
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Coastal Horizons
From $2450 to $7700 per week
  • On our Professional Linen Service Program
  • Brand new elevated luxury property with elevator
  • Less than a 1 minute walk to the Gulf beaches
  • 6 bedrooms and 4 bathrooms
  • Private heated pool with spa
  • Covered lanai with outdoor bar-shared boat dock
  • 5 King bed and 2 Twins-Sleeps 12 total
  • Close walk to The Historic Bridge Street, restaurants and shops
  • Close to the Bradenton Beach fishing pier
  • Dog friendly property for an extra fee
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View Of The Gulf
From $2450 to $8400 per week
  • Luxury Island style 7 bedroom home 
  • Directly across the street from the beach
  • Beautiful Gulf views from three levels of decks
  • Exquisitely furnished with original artwork
  • Heated pool with Tiki bar under covered porch
  • 2 master bedrooms with private deck
  • 4 full and 1 half bathroom
  • Generous living room, den and poolside family room
  • Central kitchen with seating for 13
  • Marble bathrooms with granite counters
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Hunters Point
From $3500 to $7000 per week
  • On our Professional Linen Service Program
  • Large Luxury compound- Over 5000 sq ft
  • 6 bedrooms and 5.5 bathrooms, guest house
  • Sleeps 12 in beds, 14 total allowed- 5 Kings, 2 Twins
  • Oversized heated pool with colored lighting
  • Deep water boat dock
  • Incredible water views from all around the property
  • Elevator, Pool table, Ping Pong table
  • Over 500 ft of water-frontage
  • over 1000 sq ft of balconies
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Summer Sands
From $2100 to $7000 per week
  • On our Professional Linen Service Program
  • New construction-5 bedroom + bonus room and 4.5 bathrooms
  • Spacious rooftop deck with Gulf and Bay water views
  • Private heated pool with spa and BBQ grill, foosball table
  • Just a short 2 minute walk to the Gulf beaches-Bikes and beach cart provided
  • Fully stocked kitchen with new stainless steel appliances
  • 4 Kings, 2 Twins, 1 Queen sleeper sofa-sleeps 12 total
  • Wireless Internet, HD TV's , X-Box gaming system and old school arcade game with over 200 games
  • Centrally located on the Island-walk to Sharky's Grill and short drive to local restaurants and shops
  • Dog friendly property for an extra fee
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Tropical Hideaway
From $2625 to $8400 per week
  • On our Professional Linen Service Program
  • Amazing new 7 bedroom and 7 bathroom luxury home
  • Sleeps 14 in beds, 16 total
  • Views of the Gulf of Mexico and Bay waters throughout
  • One minute stroll to the Gulf beach
  • Rooftop deck with 360 water views
  • Private heated pool with spa
  • Covered patio and multiple covered decks
  • Close walk to local restaurants and shops
  • Dog friendly property for an extra fee
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Villa La Concha
From $2450 to $8400 per week
  • New luxury Island home - North End
  • 5 bedrooms, 4.5 baths with bonus 6th room- sleeps 12 total in beds
  • Only 1 minute stroll to the beach- West of Gulf Drive!
  • Private heated pool with umbrella and attached spa
  • Pool-side covered lanai with outdoor seating and BBQ grill
  • Fully equipped kitchen with stainless steel appliances
  • Flat-screen TV's throughout and Wireless Internet
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Malibu Beach
From $2800 to $13202 per week
  • On our Professional Linen Service Program
  • New Construction Luxury Home
  • 8 bedrooms and 7.5 bathrooms
  • 7 King beds, 2 sets of bunk beds, 1 sleeper sofa-Sleeps up to 20
  • Just a short 3 minute stroll to the Gulf beach- short walk to restaurants and shopping
  • Tropical backyard with a deluxe private heated pool with a waterslide, spa and a swim-up Tiki table
  • Rooftop deck with incredible Gulf and Bay water views
  • Fully stocked kitchen with brand new stainless steel appliances
  • Wireless Internet, Flat Screen TV's throughout, Xbox gaming system
  • Foosball table, pool side covered lanai, gas BBQ grill and tropical landscaping
Book now
Mandalay Bay
From $5250 to $15842 per week
  • On our Professional Linen Service Program
  • Luxury furnishings and professional decor
  • 7 Beds + office, 6 full baths, 2 half baths, elevator
  • 6 Kings, 2 sets of bunks and 1 Queen sleeper sofa
  • Rooftop deck with sweeping views from all areas
  • Private heated pool with waterfall and large hot tub
  • 2 Full gourmet kitchens- one up and one down
  • Additional outdoor summer kitchen on the porch
  • X-Box 360 system, Foosball table and old style arcade game with over 200 different games, Cornhole boards
  • Private dock- boating and fishing, has green Snook lights
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Surf View
From $2975 to $13202 per week
  • On our Professional Linen Service Program
  • New 8 bed/6 bath construction-3,800 sq ft.
  • Private heated pool with water slide, spa and a swim-up Tiki table
  • Pool-side lanai with bar, TV, outdoor Pool table
  • Rooftop deck with hot tub and Gulf and Bay water views
  • Just a short 2-3 minute walk to the beach-Walking distance to Island shops and restaurants
  • Fully stocked kitchen with stainless steel appliances, 2 sets of washers and dryers
  • Wireless Internet, Flat Screen TV's and a X-Box gaming system
  • 6 Kings, 2 Sets of Twin Bunks, 1 Twin over Full Bunk bed with pull-out trundle + 1 Full sleeper sofa
  • Dog friendly property for an extra fee
Book now
Antigua Bay
From $2450 to $7700 per week
  • On our Professional Linen Service Program
  • Pool table, Foosball table, X-Box, Stand up Arcade game
  • 5 bedrooms and a den, 4 full bathrooms
  • Rooftop deck with beautiful views of the Island and the Gulf
  • Private heated pool with spa surrounded by lush tropical landscaping throughout
  • 4 Kings and 2 sets of bunk beds-Sleeps up to 12
  • Just a short 2 minute stroll to the Gulf Beach
  • Close to local restaurants and shops- Pine Avenue
  • Dog friendly property for an extra fee
Book now
Hemingway House
From $2100 to $7700 per week
  • New elevated luxury rental home
  • 6 Bedrooms and 6.5 bathrooms with roof top deck
  • Private heated wrap around pool with spa and in pool table
  • Only a short one minute stroll to the Gulf beach
  • Fully stocked kitchen with granite countertops and stainless steel appliances
  • 2 Kings, 2 Queens, 4 Twins and 2 Queen sized sleeper sofas-Sleeps up to 16
  • Each room has its own private or en-suite bathroom
  • 7 TV's, Wireless Internet, Cable and 1 DVD player
  • Washer and dryer in property
  • Garage
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Tropical Oasis
From $2800 to $13202 per week
  • On our Professional Linen Service Program
  • Amazing 8 bedroom luxury home
  • Sleeps 16 in beds
  • Views of the Gulf of Mexico
  • One minute stroll to beach
  • 5.5 bathrooms
  • Over-sized heated pool with hot tub and swim-up Tiki table
  • Pool Lanai with bar and TV
  • Rooftop deck with water view
  • Dog friendly property for an extra fee
Book now
Summer Sun
From $2100 to $7000 per week
  • On our Professional Linen Service Program
  • New 5 bedroom and 5.5 bathrooms custom luxury home
  • Rooftop deck with Gulf and Bay water views- large views of the Bay from the home
  • Private heated pool with spa and BBQ grill, Foosball table
  • Just a short 2 minute walk to the beaches-6 bikes, 2 beach carts and 10 beach chairs provided
  • 4 Kings and 1 bunk bed: Sleeps 10 total
  • Fully stocked kitchen with stainless steel appliances
  • Walking distance to the historic Bridge Street, restaurants, shops, mini golf
  • Wireless Internet, 8 HD TV's, 2 X-Box systems
  • Dog friendly property for an extra fee
Book now
Gulf View Beach House
From $2100 to $8253 per week
  • On our Professional Linen Service Program
  • New 5 bedroom, 3.5 bathroom construction
  • 30 second walk to Gulf beach-Multiple sweeping Gulf water views-3 Balconies with water views
  • Rooftop deck with 360 degree water views of both Gulf and Bay
  • Private heated pool with spa and patio furniture
  • 2 minute walk to multiple restaurants, Short walk to Pier and Marina
  • 2 Master suites with private baths-3 King beds, 1 set of Bunk Beds, 2 Twins-Sleeps 10 in beds, 12 total
  • HD TV's in each bedroom+ living, Wireless Internet
  • Washer and Dryer in property and a 2 car garage-Beach cart, chairs, toys and 2 bikes available for guest use
  • Adjacent to gated public playground
Book now
A Bean Point Paradise
From $2198 to $7259 per week
  • On our Professional Linen Service Program
  • Located on the prestigious Northern End, just a short walk to Bean Point beach
  • 5 bedrooms, 4.5 bathrooms-Sleeps up to 12
  • Private heated pool with spa
  • 2 Kings, 2 Queens, 2 Twins and 1 Queen sleeper sofa
  • Multiple balconies
  • 3,200 sq. ft.
  • Elevator and 2 car garage
  • 2 Master bedrooms
  • Dog friendly property for an extra fee
Book now
Sunset Surf
From $2100 to $8400 per week
  • On our Professional Linen Service Program
  • Brand new custom luxury elevated home
  • Only a 1 minute stroll to the Gulf beaches
  • 6 bedrooms and 4 full with 2 half baths
  • Rooftop deck with stunning views of both the Gulf AND Bay waters
  • Tropical private heated pool with spa
  • Professionally decorated throughout
  • 5 King beds and 1 full over full bunk bed, 1 Full Sleeper sofa--Sleeps 15 total
  • 10 beach chairs, 2 beach carts, Ping Pong and Foosball table
  • 8 Brand new flat screen TV's, 3 DVD Players, 2 Blu Ray Players, a Wii and Xbox gaming system
Book now
Atlantis Beach House
From $2975 to $13000 per week
  • On our Professional Linen Service Program
  • New 9 bedroom and 6.5 bathroom luxury home
  • Rooftop deck with amazing Gulf and Bay water views
  • Private heated pool with water slide, spa and a swim-up Tiki table, pool-side lanai with bar, TV, Ping-Pong, Foosball and a Pool table
  • Only a short 2 minute walk to the renowned Gulf beaches
  • 7 Kings, 1 Queen, 2 sets of Twin bunk beds, 1 trundle, 1 Day bed with trundle, and 1 Queen sleeper sofa-sleeps 24 total
  • Fully stocked kitchen with new stainless steel appliances-2 sets of washers and dryers
  • Professionally decorated
  • Wireless Internet, Flat Screen TV's, X-Box gaming system and more
  • Dog friendly property for an extra fee
Book now
Blue Water View
From $2450 to $8400 per week
  • On our Professional Linen Service Program
  • Beautiful Gulf water views, only 1 minute walk to the beach-located on a quiet residential street
  • 6 bedroom/5 full baths-Sleeps 14 in beds, 16 total
  • Heated pool and spa with swim-up tiki hut, tropical landscaping, gas BBQ grill and pool-side lanai with bar/TV and pool stereo
  • Wireless Internet and Flat Screen HD TV's
  • Granite, Travertine
  • Ping Pong table, Bocce Ball or Cornhole court
  • Multiple balconies and a wrap around porch
  • 4 Suites with King beds, 2 Twin beds, 1 set of Bunk Beds (Twin over Full bed with pull out Trundle)
  • Queen sleeper sofa
Book now
Conch House
From $2450 to $8400 per week
  • On our Professional Linen Service Program
  • New 6 bedrooms and 4.5 bathrooms private home
  • Deluxe tropical pool with Water Slide and Unique Enclosed "Grotto" Spa
  • Pool Lanai with bar, TV and Gas BBQ-Back Porch Balcony
  • Travertine Marble Floors and high-end bathroom fixtures
  • Some 3rd level Gulf water views
  • 4 minute walk to the beach
  • Flat Screen HD TV's, Ping-Pong table, Wii and X-Box Game Systems, IPod Docking Station, Wireless High-Speed Internet
  • 4 King beds, 2 Twin beds, 1 Twin over Full sized Bunk Bed w/Trundle and Pull-Out Sleeper Sofa-Sleeps 14 in beds, 16 total
  • Dog friendly property for an extra fee
Book now
The Bayfront
From $2205 to $8400 per week
  • On our Professional Linen Service Program
  • Direct Bay Front 3600 sq. ft. luxury home
  • Deep-water dock, heated pool and spa
  • 6 bedroom, 4 full bathrooms
  • 2 separate full gourmet kitchens
  • New heated pool and spa-covered poolside lanai
  • Custom cabinets, granite, tile
  • New travertine floors
  • New 2nd level screened porch
  • 2 separate washers/dryers
Book now
Gulfside Oasis
From $2800 to $9100 per week
  • On our Professional Linen Service Program
  • New luxury construction-3,400 Sq Ft.-6 bed/5 bath
  • Multiple large views of Gulf waters and multiple balconies
  • One minute walk to the beach and Beach Bistro
  • Private heated pool w/ spa
  • Gourmet kitchen, fully equipped
  • 2 washers and dryers
  • 60" Smart TV in living room, Flat screen TV's in all rooms, Wireless Internet, Foosball, Ping Pong
  • 5 King, 4 Bunk Beds, Pull out sleeper sofa-Sleeps 14 in beds, 16 total
  • 3 rooms have in-suite bathrooms-Jacuzzi tub in Master bedroom
Book now
Pearl Beach
From $2450 to $9352 per week
  • On our Professional Linen Service Program
  • New luxury elevated property
  • Only a brief 2-3 minute stroll to beach
  • Deluxe private hedated pool with spa, water slide and covered pool-side lanai
  • 3 Master suites each with a private bath
  • Fully equipped with gourmet kitchen
  • Granite, travertine throughout
  • Washer and Dryer
  • 2 car garage with ping pong table
  • Wireless Internet
Book now
Tiki Beach
From $2800 to $8400 per week
  • On our Professional Linen Service Program
  • New 6 bedroom and 5.5 bathroom luxury private home
  • Multiple covered decks-Gulf water views
  • Just a short 1 minute walk to the beach
  • 5 Kings and 1 set of bunk beds-sleeps 12 in beds
  • Private heated pool with sun deck and spa, outdoor shower and covered lanai
  • Short 10 minute stroll to local eateries and shops on North AMI
  • Wireless Internet and 8 Flat Screen TV's
  • Gourmet kitchen with stainless steel appliances, granite throughout
Book now
Beachside Oasis
From $2450 to $6825 per week
  • Less than a 1 minute walk to the Gulf beaches
  • 5 bedrooms and 3.5 bathrooms--custom built luxury home
  • 1 King, 3 Queens, 2 sets of bunks, 1 Queen sleeper--Sleeps a total of 14
  • Rooftop deck with beautiful Gulf AND Bay water views
  • Private heated pool with covered lanai
  • 4 open air decks with outdoor seating
  • Short walk to local restaurants and shops
  • Granite countertops, crown molding and custom tile
  • 7 Flat screen TV's and 3 DVD players
Book now
Beachfront Paradise
From $4007 to $16940 per week
  • On our Professional Linen Service Program
  • Brand new luxury beach front elevated home
  • 6 bedrooms, 4.5 baths with 2 Master suites overlooking the Gulf beaches
  • Resort style private heated pool with spa and outdoor kitchen
  • Private beach access via a dune walkover
  • Superb Gulf views throughout-2 separate living areas with amazing views
  • Professional chef's kitchen and a kitchenette on the top living level
  • 4 King beds, 2 sets of bunks with twin over full and 2 sleeper sofas-Sleeps 18 total
  • Flat screen TV's in each bedroom and living room
  • 2 sets of washer and dryer-one on each living level
Book now
Bay View
From $1750 to $5880 per week
  • On our Professional Linen Service Program
  • Direct Bay front with open water views-only a 3 minute walk to the Gulf beach
  • Private tropical heated pool
  • Oversized balcony with furniture/tables
  • Private dock for keeping a boat or fishing
  • Flat screen TV's throughout and Wireless internet
  • Fully equipped kitchen with an efficiency kitchen downstairs
  • 4 king beds and 1 with 2 sets of bunk beds, sleeps up to 14 comfortably
  • Dog friendly property for an extra fee
Book now
Angel Sea
From $2100 to $5880 per week
  • Luxury Mediterranean Style Villa, Professionally Decorated
  • Coastal themed furniture
  • Elevator to all three floors
  • 6 bedrooms, 3.5 bathrooms, 2 King suites, Sleeps 2-12 guests in stylish comfort
  • 3-4 Minute stroll to the beach
  • Large heated private pool, BBQ Grill and Patio Furniture
  • Four King beds, One Queen, two Twins and a sleeper sofa
  • 50in HDTV and Blu-ray player, Flat Screen TV In Every Bedroom
  • Cable, Wii System, DVD players, Complimentary US Phone Calls, Wi-Fi
Book now
The Big Yellow House
From $3003 to $9800 per week
  • On our Professional Linen Service Program
  • Direct Gulf Front Home- right on the beach!
  • 5 bedrooms, 4 bathrooms
  • Sleeps up to 10 in beds, 14 total
  • Private heated pool, beachside
  • 3000 Sq Feet- multiple living rooms
  • Cable TV, Unlimited local/ long distance, wireless internet
  • Fully equipped kitchen on lower level
  • Kitchenette area on upper level
  • Washer and Dryer, lots of amenities
Book now
Paradise Beach
From $3500 to $16800 per week
  • On our Professional Linen Service Program
  • Brand new luxury beach front elevated home
  • 8 bedrooms, 6.5 baths with 5 Master suites
  • Superb Gulf views throughout--multiple decks
  • Resort style private heated pool with spa and pool side bar
  • Private beach access via a dune walkover
  • 7 King beds and a twin over full bunk bed-Sleeps 17 total
  • 10 beach chairs, 2 beach carts, Ping Pong, Foosball plus a Xbox gaming system
  • Elevator available to all floors
  • Dog friendly property for an extra fee
Book now
Lighthouse Lagoon
From $2100 to $8400 per week
  • On our Professional Linen Service Program
  • Elevated 5 bed and 4 full baths
  • Uniquely shaped heated tropical pool
  • City of Anna Maria-North-end
  • 1 minute walk to Pine Ave, 2 minutes to the Pier and 6 minutes to the Gulf beaches
  • New above ground hot tub being added in May of 2016
  • 2 screened-in back porches-Skyway bridge views
  • 4 Bikes, a beach wagon, 2 beach chairs, bocce ball and paddle ball provided
  • Wireless Internet, flat screen TV's and a XBOX gaming system
  • Dog friendly property for an extra fee
Book now
Willow Beach House
From $2800 to $12870 per week
  • This home only allows Saturday-Saturday bookings
  • Newly renovated canal front home
  • 5 bedrooms and 3.5 bathrooms
  • Accommodates up to 16--1 King, 3 Queens, 1 Set of Bunk Beds with Trundles, 2 Twins, 1 Queen sleeper sofa
  • Only 1 block to beaches
  • Private pool with spa, Gas BBQ grill and outdoor shower
  • Fully stocked gourmet kitchen with all new Viking appliances
  • Wireless internet, 5 Flat screen TV's, Blue-Ray Player and Stereo System
  • Large screened-in patio and 3 balconies
  • Garage and covered parking-Washer and dryer in unit
Book now
Seaside Escape
From $2800 to $8400 per week
  • On our Professional Linen Service Program
  • New 7 bedroom and office room, 6 full and 2 half bathrooms
  • Rooftop deck with both Gulf AND Bay water views
  • Just a short 1 minute walk to the Gulf beach
  • 6 Kings and 3 Twins (1 bunk bed with pull out trundle)-Sleeps 15 total
  • Private heated pool with spa, outdoor shower and covered lanai
  • Ping Pong table, 9 Flat Screen TVs, outdoor shower
  • Only a 1 minute stroll to Bay waters
  • 10 beach chairs and 2 beach carts available for guest use
  • Dog friendly property for an extra fee
Book now
Tortuga Bay
From $2450 to $7700 per week
  • On our Professional Linen Service Program
  • Luxury one-level home on canal
  • 1 minute stroll to beach
  • 5 bed- 3 bath
  • Over-sized heated tropical pool
  • Great water slide into pool-large dock and close to open water
  • Complete renovation of home-luxury amenities throughout
  • Large yard- plenty of room
  • New granite, marble, tiles
  • Dog friendly property for an extra fee
Book now
Tahiti Bay
From $2450 to $7000 per week
  • On our Professional Linen Service Program
  • Brand new construction
  • 5 bedrooms, 4 bathrooms
  • Private heated pool with spa, Pool and Foosball table, BBQ grill
  • 4 Kings, 2 bunk beds, 1 Sleeper Sofa
  • Sleeps up to 14
  • Rooftop deck with beautiful views
  • Short 2 minute stroll to the Gulf
  • Close to local restaurants and shops-Ginny's and Jane's Bakery and Pine Avenue
Book now
Coral Retreat
From $2100 to $6300 per week
  • On our Professional Linen Service Program
  • Elevated 5 bed, 3.5 bath private home
  • Private heated pool with spa, covered lanai with pool side bar, flat screen TV and BBQ grill
  • Short 4 minute stroll to the Gulf beaches
  • 3 Kings, 2 Queens-Sleeps up to 10
  • Mature tropical landscaping
  • Flat Screen TV's throughout-Classic stand up arcade game with over 200+ games and a Ping Pong table
  • 2 Car garage
  • Pack-n-Play available for guest use
Book now
Villa Del Sol
From $2975 to $7700 per week
  • On our Professional Linen Service Program
  • Canal home with boat dock
  • 5 bedrooms, 3 full bathrooms
  • Sleeps up to 10 in beds
  • 2800 Sq Feet of living space
  • 2 car garage + 4 car driveway 
  • Ground level home
  • Fully equipped kitchen
  • Cable TV, Wireless Internet, Unlimited local and long distance
  • 1 King, 2 Queens, 3 sets of Bunk Beds
Book now
Bayblue
From $2450 to $7000 per week
  • Fabulous Bay water views, Private dock, 2-3 Minute stroll to Gulf beach
  • Multiple balconies- water views
  • Private heated pool, Gas Grill
  • High-end finishings
  • Luxury furniture and fixtures
  • 6 Bedrooms - 4 Bathrooms, Sleeps up to 18
  • Private 120' boat dock (lift not available for guest use)
  • Elevator
  • 2 fully equipped Kitchens-Great for multi-family stays
  • 2 sets of washers/dryers
Book now
Villa Portofino
From $1750 to $8253 per week
  • Mediterranean style Island Villa with tropical themed furniture throughout
  • 2 King beds, 1 Queen bed, 4 Twins -Sleeps 10 in beds and up to 11
  • 5 bedroom, 3.5 bathroom
  • Two Master suites
  • HD TV and HD-DVD in living room, XBOX, HD TVs in all bedrooms and wireless Internet
  • Large Garage
  • Premium linens and towels
  • Private heated swimming pool with tropical landscaping, ping-pong table and only a 3 minute stroll to the beach
  • Washer and Dryer
  • Luxury kitchen, fully stocked
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Sunset Landing
From $2100 to $7700 per week
  • On our Professional Linen Service Program
  • New luxury rental home-5 bed+ bonus room, 4.5 baths
  • 4 Kings, 1 Full, 1 Pull out trundle bed- sleeps 12 total
  • Private heated pool with lanai and BBQ grill
  • West of Gulf Dr-2 minutes to beach
  • Island style interior-professionally decorated
  • HD flat screen TV's in all bedrooms and wireless Internet
  • Brand new Foosball table on lanai and X-Box gaming system
  • Dog friendly property for an extra fee
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The Blue Horizon
From $4900 to $18000 per week
  • Direct Gulf Front- 2 buildings
  • 9 bedrooms total- sleeps 21 total
  • 6 bedrooms in main house
  • 3 bedrooms in guest house
  • Sits directly on the beach
  • Multiple Panoramic Gulf views
  • 3 bedroom also has Gulf views
  • Private heated pool-large hot tub that holds 10
  • 2nd level beachfront deck
  • **Special Events are Subject to Additional Fees-All Guests Must Sign a Separate Rental Agreement-Contact the Reservations Team for More Information**
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Whitecaps
From $2100 to $7000 per week
  • On our Professional Linen Service Program
  • Luxury custom 5 bedroom, 3.5 bathroom home
  • Views of the Gulf of Mexico beaches and water-Only 1 minute stroll to the beach
  • Located on the prestigious North end of the Island
  • Heated pool, covered lanai area, gas grill, covered porch with a flat screen HD TV
  • Flat screen HD TV's in each bedroom, Wi-Fi Internet
  • 2 Kings, 2 Queens, 2 twin beds-Sleeps 10 in beds, 12 total
  • High-end kitchen-washer and dryer
  • Elevator accesses to all floors, luxury marble, flooring, fixtures and fine linens
  • Dog friendly property for an extra fee
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Beachbreeze
From $2450 to $7700 per week
  • On our Professional Linen Service program
  • Luxury property, NOTE new full 4th bathroom will be added by 10/2016!
  • Six bed, 3.5 bath-Sleeps 12 in beds, 14 total allowed
  • West of Gulf Dr- one minute stroll to Gulf beach
  • Heated pool with spa and waterfall, BBQ grill, outdoor kitchen with flat-screen TV, outdoor Pool table
  • Rooftop deck for fabulous views of the Gulf water
  • Three additional balconies with great island views
  • Three kings, two queens and one set of bunk beds
  • 72in Hi Def TV and Blu-ray player, 2 leather power recliner love seats, Flat-screen TV's in all bedrooms, Cable, Xbox gaming system, DVD and Internet
  • Outdoor Billiards table, Foosball Table and classic Arcade style video game with over 200 games to choose from on it
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South Seas
From $2450 to $9352 per week
  • On our Professional Linen Service Program
  • New 6 bedroom Island home
  • Short 3 minute walk to beach
  • Deluxe pool with spa
  • Huge water-slide
  • Large covered back porch lanai
  • 3rd level water views and 3 balconies
  • Ping Pong/TV
  • X-Box and Wii game stations-Ipod radios in bedrooms
  • Dog friendly property for an extra fee
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Mojito Splash
From $1800 to $8253 per week
  • On our Professional Linen Service Program
  • Tropical 5 bed/3.5 bath home
  • Short 2-3 minute walk to beach
  • Private heated pool with hot tub and separate Tiki hut and bar by the pool
  • Wireless Internet
  • Full two car garage
  • Ping Pong table
  • Covered pool lanai with TV
  • 4 Kings, Twin trundle and Queen sleeper sofa
  • Dog friendly property for an extra fee
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Lazy Lagoon
From $2800 to $9352 per week
  • On our Professional Linen Service Program
  • Brand new 5 bed and 5 bath elevated home
  • Private heated pool with spa
  • Sleeps 12 in beds-4 Kings and 1 Full sized bunk bed with 1 Queen sleeper sofa
  • Only a 1 minute stroll to the beach access-no streets to cross!
  • Professionally decorated
  • Balcony overlooking the pool
  • TV in every room, Xbox gaming system, Pool table, Wireless Internet
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Gulf View Cottage
From $1750 to $6048 per week
  • On our Professional Linen Service Program
  • Newly renovated home
  • 5 bedroom, 3/5 bath
  • 1 minute walk to Gulf beach-Outstanding Gulf water views-Beach chairs and toys provided for guest use
  • Private heated pool with spa and shallow end for young kids, pool furniture and chairs
  • Flat screen TV's throughout, Apple TV in Living Room, High Speed Wireless Internet, XBOX gaming system
  • Luxury linens and towels
  • Full gourmet kitchen and washer and dryer in property
  • Travertine and granite
  • 2 Kings, 1 queen, 2 bunks, 1 full and a pull-out sleeper sofa-Sleeps 12 in beds
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Bayfront Paradise
From $2100 to $8400 per week
  • On our Professional Linen Service Program
  • 5 bedroom custom luxury home, Direct Bay front, Located on private-secluded street
  • Heated pool with spa, Private T-Dock for fishing and boating, Multiple balconies
  • Cruise ship type views throughout
  • Luxury furnishings and fixtures, Fine marbles, Wood trim and Tiles
  • Recreation room off pool area, Wireless Internet, Flatscreen HD TV's, X-box gaming system for kids
  • Short walk to beach-Beach wagon and supplies for guest use
  • 4 King, 2 twin beds-Sleeps 10 in beds and 12 total
  • 4 full bathrooms, 1 half bath
  • Dog friendly property for an extra fee
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Harbor Breeze
From $2800 to $9898 per week
  • On our Professional Linen Service Program
  • New luxury Bayfront home with sweeping water views-private dock
  • Heated Bayfront pool with spa
  • High-end finishings, furniture, decor
  • Private cul-de-sac location
  • Large covered lanai off pool
  • Gourmet kitchen, granite counters
  • High speed internet, X-BOX Gaming System, Flat screen TV in all bedrooms, classic stand up arcade game and Ping-Pong table
  • Tropical landscaping
  • Washer and Dryer in property, 2 car garage