Searching, please wait...

Anna Maria Island 4 Bedroom Vacation Rentals

View Rentals Below

Anna Maria Island is a place where you can relax, enjoy the Florida sunshine and create memories that last forever. This Gulf Coast island has something for everyone and will offer you the best Florida beach vacation in the state.

There is an abundance of activities on the island in addition to spending the day on our amazing beaches. Take a sail, catch some large fish, see some dolphins, ride a jet ski, go paddleboarding or kayaking, play in the sand, swim in the ocean, walk our famous beaches and enjoy.

These four bedroom rentals are great for groups, multiple families, large families, and multi-couple vacations. Enjoy the spaciousness of our rentals. We are sure that there is more than enough room for everyone. Our multi bedroom homes are spectacular! We have beachfront rentals, bayfront rentals, and dog friendly rentals.

These rentals can accommodate up to 10 guests or more.

Anna Maria Island 4-bedroom vacation rentals are ideal for groups, multiple families, large families, and multi-couple vacations. The spaciousness of these rentals will really make you feel at home. Anna Maria Island has something for everyone!
Book now
Whispering Winds
From $1018 to $3409 per week
  • On our Professional Linen Service Program
  • Single Family Home at 1884 Sq Feet
  • 4 bedrooms, 2 bathrooms
  • Private heated pool with gas BBQ grill
  • 2 car garage
  • 4 TVs, 2 DVD Players, 1 VCR
  • 3 Houses to Gulf of Mexico
  • 1 King, 2 Queens, 2 Twins-Sleeps up to 8 in beds
  • Cable TV, Unlimited local and long distance, Wireless Internet
  • Fully equipped kitchen
Book now
Aqua Cove
From $1400 to $7700 per week
  • On our Professional Linen Service Program
  • Brand new home located on a canal with dock
  • Private heated pool with swim-up table
  • Covered open air balcony overlooking the pool and canal
  • 4 Bedrooms and 3.5 bathrooms-Sleeps 10
  • Tropical landscaping
  • Short 5 minute stroll to the Gulf beaches
  • Closely located to the popular Pine Avenue
  • Pool table and Ping Pong table
  • Elevator and 2 car garage
Book now
Waterside House
From $2100 to $7000 per week
  • On our Professional Linen Program
  • Newly renovated luxury private home with dock, excellent fishing, boating
  • Heated private pool overlooking the Bay
  • Elevator to all floors
  • 4 bedrooms +den and 5.5 bathrooms-3 King beds, 2 sets of bunk beds (4 Twins) and 1 Queen sleeper sofa-Sleeps 12
  • New flatscreen TV's throughout
  • Large garage and central air conditioning
  • 3 balconies with paddle fans for cooling--Ping Pong and Foosball table
  • Amazing top deck with incredible views, fishing dock and place for a boat
  • Dog friendly property for an extra fee
Book now
Hawaiian Hideaway
From $1197 to $3409 per week
  • New private duplex
  • 4 bedrooms, 2 bathrooms-Sleeps 8
  • Private heated pool with shallow entry for small children, patio furniture and BBQ grill
  • Short 4 minute stroll to beach
  • Full gourmet kitchen with stainless steel appliances, granite and fine tile
  • Charmingly decorated
  • Washer/Dryer
  • Flat screen HD TV's throughout-Wireless Internet
  • Dog friendly property for an extra fee
Book now
Away To Play
Call For Pricing
  • Large, Newly Constructed Private Home
  • 4 bedrooms, 2 1/2 bathrooms-Sleeps up to 9 in beds
  • 2,685 Sq Feet
  • Large private, heated pool, covered pool area patio, Gas BBQ grill
  • One King, Two Queen beds, one bunk bed-Master suite has private balcony
  • Washer and Dryer in property
  • Fully Equipped Kitchen, Maple cabinets and granite countertops
  • Cable TV, Unlimited local and long distance, Wireless Internet
  • 3 TVs, 1 DVD Player
  • 2 Car Garage
Book now
Breakaway
From $2100 to $7042 per week
  • On our Professional Linen Service Program
  • Bay-Front Ground Level Home
  • 4 bedrooms, 2 bathrooms-Sleeps 8 in beds, 10 total
  • 2000 Sq Feet- new renovations
  • New private heated pool, Outdoor Shower and gas BBQ grill
  • Ceiling to floor windows in living room
  • Views of Tampa Bay and Skyway Bridge, Just a short walk to Bean Point and Rod n Reel Pier
  • 1 King, 1 Queens, 2 Twins, 1 Twin Over Full Bunk
  • Fully equipped kitchen
  • Cable TV, Unlimited local and long distance, Wireless Internet, 2 TV's and 1 DVD Player
Book now
Whispering Whale Retreat
From $1575 to $3708 per week
  • Newly remodeled elevated home
  • 4 bedrooms, 2 bathrooms-1 King, 1 Queen, 2 Twins, 2 Bunk Beds
  • Sleeps up to 10 in beds
  • Large heated private pool
  • Expansive deck overlooking the pool
  • Northern End of Anna Maria Island- Short walk to Pine Ave.
  • Gourmet kitchen and a gas fireplace
  • Washer and Dryer in property
  • 4 Flat-screen TV's and a wireless printer,
  • Beach towels for guest use
Book now
Tarpon Pointe
From $1750 to $5390 per week
  • North-end home on canal
  • Dock, heated pool, porches
  • Newly redecorated, upgrades
  • Granite counters
  • 4 bedroom, 3 full baths
  • 2 Kings, 1 full sized bunk, 1 Twin over full bunk and 1 Queen
  • Short walk to Pine Ave.--Quiet side street
  • Short walk to Bay beach and pier
  • Flat screen HD TV's
  • Washer/Dryer
Book now
Sunchase Villa
From $1750 to $5390 per week
  • Gulf Front Single Family Home-"Old Florida" Cottage
  • 4 bedrooms, 4.5 bathrooms
  • 1609 Sq Feet
  • Washer and Dryer
  • Located in Beautiful Anna Maria City
  • Fully equipped kitchen
  • Satellite TV, Unlimited local and long distance
  • Wireless Internet
  • Screened Lanai facing the Gulf of Mexico
  • 3 TVs, 1 DVD Player
Book now
Sundown South
From $1498 to $6050 per week
  • On our Professional Linen Service Program
  • Ground level- new renovation
  • Private, heated salt water pool
  • Lakefront water views
  • 2-3 minute stroll to Pine Ave activities
  • 2-3 minute stroll to beach
  • Large wood deck- pool furniture
  • Stainless steel BBQ grill
  • Flat screen HD TV's throughout
  • Beach chairs/amenities provided
Book now
Avenue E By The Sea
From $1750 to $5390 per week
  • On our Professional Linen Service Program
  • Newly constructed, elevated home
  • 4 bedrooms, 3 1/2 bathrooms
  • Sweeping views of the blue Gulf water, easy 2 minute stroll to Gulf beaches
  • Sleeps 8 in beds-2 Queens, 2 Twins, 1 Set of Twin Bunk beds
  • 2 separate living areas, flat screen HD TV's throughout, elevator
  • Fully equipped kitchen with stainless steel appliances, granite countertops, washer and dryer
  • Private heated pool with Cabana area-Foosball table
  • Spiral staircase to rooftop deck
  • Covered 1st level deck
Book now
Bimini Breeze Beachhouse
From $1750 to $6048 per week
  • Newly renovated elevated private home with solid quartz countertops and herringbone porcelain tile floors; double vanities in all bathrooms
  • 4 bedrooms and 3 bathrooms--Sleeps 10 total. 1-2 minute walk to the beach.
  • Master suite includes private balcony, built-in desk, sitting area, spacious bathroom, walk-in 5x5 closet for storing suitcases or a pack n' play.
  • Brand new private heated pool (with sun bench) with spa
  • Tankless hot water - everyone gets a hot shower; Outdoor shower includes hot water
  • Outdoor Tiki bar, game area with foosball table, cornhole/beanbag toss, poolside TV, and refrigerator. Gas grill for guest use
  • 2 minute walk to the intracoastal waterway, Historic Bridge Street, Bradenton Beach Pier, Marina with boat rental
  • Flat screen TV's with cable throughout - every bedroom, living room, and poolside, most with Netflix, and a living room Xbox gaming system
  • 2 Shaded breezeways to relax in - one is adjacent to the pool, other with conversation area and hammock and ring game
Book now
Bahama Breeze
From $2100 to $4550 per week
  • On our Professional Linen Service Program
  • Newly renovated elevated 4 bedroom and 3 bathroom home
  • Short 5 minute walk to the Gulf or Bay beaches-great location!
  • 3 King beds and 1 bunk bed: Sleeps 8 total
  • Brand new tropical private heated pool with spa
  • 8 beach chairs, 6 bikes and 2 beach carts provided for guest use
  • Xbox gaming system and 6 flat screen TVs
  • Pool table, Foosball table and Ping Pong table
  • Short walk to Pine Avenue: restaurants and shops
  • Dog friendly property for an extra fee
Book now
Villa Milano
From $1750 to $5390 per week
  • On our Professional Linen Service Program
  • 4 bedrooms & 4 full bathrooms
  • Very large- 3,750sq ft under roof
  • Just 2-3 minutes stroll to the beach
  • Tropical heated pool and game room located just off of the lanai
  • Including 2 King size Master Suites
  • Mediterranean Design with Tower
  • Dual central air, elevator, stairs and decorative fireplaces
  • Top of the range sofas & beds
  • Pet-Friendly
Book now
Skip To The Beach
Call For Pricing
  • Gorgeous custom luxury property with Gulf views throughout
  • 4 bedrooms and 4 bathrooms
  • Only one house away from the Gulf beaches-rooftop deck with Gulf views
  • 1 King bed, 2 Queens, 1 Twin and 1 Twin over Full bunk bed: Sleeps 10 total
  • Private heated pool surrounded by tropical landscaping
  • 2 Bikes, 4 beach chairs and 1 beach cart provided for guest use
  • 6 flat screen TVs and 1 DVD player
  • Custom made table that can be used for poker, bumper or even a dining table
  • Multiple open air decks with beautiful views
  • Fire pit with seating area by the pool
Book now
Coral Cove
From $1750 to $5145 per week
  • New elevated Island home
  • 4 bedrooms and 3.5 bathrooms-very spacious bedrooms
  • Private heated pool
  • Multiple balconies, views of Gulf and Bay water
  • Only 2 minute walk to the beach
  • 2 Kings, 1 Queen and 2 Full size beds
  • Washer/Dryer and Garage
  • Wireless Internet, Playstation gaming system and flat screen TV's
  • Fully stocked kitchen with new stainless steel appliances
Book now
Beach Harbor
From $1750 to $6048 per week
  • Brand new construction luxury property
  • Beautiful Bay views from the rooftop deck
  • 4 bedrooms and 3 full with 2 half baths
  • Private heated pool with spa-covered lanai
  • Only a 3 minute stroll to the Gulf beaches
  • 3 King beds, 2 bunk beds-Sleeps 10 total
  • Gourmet kitchen with granite counters
  • Covered decks
  • Tropical landscaping
  • Dog friendly property for an extra fee
Book now
Cabana Breeze
From $1750 to $5390 per week
  • On our Professional Linen Service Program
  • Elevated Island home-brand new private pool
  • New recreation room and pool-side cabana
  • Located on the prestigious Northern End of Anna Maria Island
  • 4 bedrooms and 2 bathrooms-2 Kings, 2 Queens, 1 sleeper sofa-Sleeps up to 10
  • Just a short walk to the Anna Maria Island City Pier
  • 4 Bikes, a beach wagon, 4 beach chairs, beach umbrella, bocce ball and paddle ball provided
  • Short walk to Pine Avenue and all of its shops and restaurants
  • Flatscreen TV's in every bedroom, wireless Internet and XBOX gaming system, and Foos ball
  • Dog friendly property for an extra fee
Book now
Pelican Villa
From $1466 to $5390 per week
  • On our Professional Linen Service Program
  • Single family home
  • 4 bedrooms, 3 bathrooms-Accommodates up to 8
  • 2400 Sq Feet
  • Private heated pool
  • Large covered patio pool area
  • Crown molding throughout
  • Gourmet kitchen with large pantry
  • Granite counter tops and custom cabinets
  • Formal dining room
Book now
Blue Heron
From $1750 to $5390 per week
  • On our Professional Linen Service Program
  • Multiple balconies- front and back
  • Private heated pool, pool-side lanai with TV, umbrella in pool for shade and lush tropical landscaping
  • Only a short 3 minute stroll to beach
  • 4 bedroom/ 3.5 bathroom-Sleeps 8 total
  • Master bedroom balcony
  • Flat screen TV's throughout, Wii gaming system, Ping-Pong table and rec area with TV
  • Full gourmet kitchen
  • Pull out sleeper sofa
  • Granite counters/custom cabinets
Book now
Breezy Beach
From $1400 to $4066 per week
  • On our Professional Linen Service Program
  • Brand new elevated private duplex
  • 4 bedrooms and 4 bathrooms-Sleeps 8 in beds, 10 total
  • 3 Kings, 1 Bunk bed, 1 Queen sized sleeper sofa
  • Private heated pool with spa, tropical landscaping, gas BBQ grill
  • Short 5 minute stroll to the Gulf beaches
  • Professionally decorated
  • 5 TV's and 1 DVD player, Wireless Internet-Rec room with Foosball table and couch
  • 2 car garage
Book now
Sunshine Reef
From $2100 to $5600 per week
  • On our Professional Linen Service Program
  • 4 bedrooms and 4 bathrooms-3 en-suites
  • Private heated pool with sun shelf and swim up Tiki table
  • Covered outdoor living area with a bar, TV and lots of seating
  • 1 King, 2 Queens, 1 sets of bunk beds-Sleeps 10
  • Less than a 5 minute stroll to the Gulf beaches
  • Only two blocks away from the popular Pine Avenue
  • Flat screen TV's throughout, Wii gaming system, beach cart and 3 adult bikes
  • Granite counters, stainless steel appliances, outdoor shower and more
Book now
Casa Del Playa
From $1400 to $4998 per week
  • On our Professional Linen Service Program
  • 4 bedrooms and 3 bathrooms-Sleeps 10 total
  • Separate 1 bed/1 bath suite with a kitchen and living area
  • 3 Kings, 2 Twins, 1 Queen sized sleeper sofa
  • Private heated pool with spa, tropical landscaping, BBQ grill
  • Only a 2 minute stroll to the Gulf beaches
  • Short 2 minute walk to Island shops and restaurants
  • TV in each bedroom
Book now
Seahorse Beach House
From $2000 to $4900 per week
  • On our Professional Linen Service Program
  • 4 bedrooms, 3 bathrooms
  • Private heated pool with BBQ grill
  • Short 4 minute stroll to beach
  • Full gourmet kitchen with stainless steel appliances, granite and fine tile
  • Professionally decorated, all brand new furniture
  • 3 Kings, 1 bunk bed, 1 Queen sleeper-Sleeps 10
  • Washer/Dryer
  • Flat screen TV's throughout-Wireless Internet and Xbox gaming system
Book now
Egrets Nest
From $1018 to $3409 per week
  • Ground level, newly remodeled
  • Private heated pool-Outdoor table and chairs
  • 4 Bedroom, 2.5 Bathrooms-Sleeps up to 8
  • 2 Kings, 1 Queen and 2 Twins
  • Full gourmet kitchen-Stainless steel appliances
  • BBQ Grill
  • Wireless Internet
  • Brisk 4 minute walk to the beach
  • Centrally located on the Island, close to many amenities
Book now
Ocean Walk
From $2100 to $8253 per week
  • On our Professional Linen Service Program
  • New construction
  • Private heated pool with spa
  • 4 bedrooms and 3.5 bathrooms
  • 3 Kings, 2 Sets of Bunk Beds, 1 Queen Sleeper Sofa-Sleeps 10 in beds and 12 total
  • Short 2 minute stroll to the beach- West of Gulf Dr.
  • Fully stocked kitchen with new stainless steel appliances
  • Small loft and gaming area
  • Wireless Internet, Flat screen TV's, X-Box gaming system
  • 6 Bikes, beach wagon, chairs and toys provided for guest use
Book now
Casa Laguna
From $2975 to $6300 per week
  • Deluxe Island style Bay front home on a secluded lagoon location-Great for fishing!
  • Prestigious North Longboat Key location, 5 minutes from Bridge Street
  • Full size heated, screened pool with spa and a huge balcony with incredible views
  • The finest furnishings and decor, travertine tiles and hardwood floors
  • Fully stocked gourmet kitchen with deluxe appliances, wine captain and ice maker
  • Summer kitchen on lanai, bar, TV, granite throughout
  • House sits on a double lot- lush tropical landscaping
  • 4 bedrooms, 4 full bathrooms-Sleeps 11 total
  • 2 King Master suites, 1 King guest bedroom, 1 twin over full bunk bed
  • HD TV's in every room, Ping-pong table, beach toys and towels
Book now
Casa Muratti
From $1750 to $5390 per week
  • Beautiful North-end location
  • 4 bed and 3.5 bath-1 King, 2 Queens, 1 Double-Sleeps up to 8 in beds
  • Private heated pool, Large Outside Covered Bar and Patio Area with Outdoor Shower
  • Gated entrance with 1 car garage
  • 2530 Sq Feet, All Bedrooms are on the Top Floor with Ceilings fans throughout
  • 1/10th Mile Walk to the Gulf of Mexico-Only 4 blocks South of the Popular Pine Avenue
  • 3 TVs, 3 DVD Players, HD TV and Wireless Internet
  • Fully Equipped Gourmet Kitchen-washer and dryer in property
  • Master Bathroom Includes double vanity sinks, Walk-In Shower and Larger Jacuzzi Tub
  • Dog friendly property for an extra fee
Book now
Harbor Haven
From $1750 to $6048 per week
  • Brand new luxury property
  • Rooftop deck with Bay water views
  • 4 bedrooms and 3 full with 2 half baths
  • Private heated pool with spa
  • Only a 3 minute stroll to the Gulf beaches
  • 3 King beds, 2 bunk beds-Sleeps 10 total
  • Gourmet kitchen with granite counters
  • Covered decks
  • Tropical landscaping
  • Dog friendly property for an extra fee
Book now
Pineapple Key
From $1400 to $6048 per week
  • Completely renovated single family home
  • 4 bedrooms and 2 bathrooms
  • 2 Kings, 1 Queen, 2 Sets of bunks, 1 Queen sleeper sofa
  • 2 Blocks from the Gulf beaches
  • Private heated pool with spa-covered living area by the pool
  • Pool table, Wii gaming system, board games, 6 TV's and 3 DVD players
  • Only 2 houses away from freeTrolley stop
  • New Travertine floors, trims, molding, granite counters and more
  • 2 Living areas-front and rear porches
Book now
Paradise On Pine
From $1897 to $8253 per week
  • On our Professional Linen Service Program
  • Located on the popular Pine Avenue- prestigious Northern end of AMI
  • Newly professionally redecorated, beautiful layout
  • Short stroll to Gulf beach, local shops, restaurants and the City Pier
  • Private heated pool, canal access and BBQ grill
  • Multiple large balconies with great water views
  • Foosball table, Wii
  • Garage and elevator, sleeps 10 in beds, 12 total
  • Dog friendly property for an extra fee
Book now
Riki Tiki
From $1750 to $5390 per week
  • On our Professional Linen Service Program
  • Only 3 houses from the beach- 30 second walk
  • 4 bedrooms and 4 bathrooms-Sleeps up to 8
  • Bamboo floors, high end furnishings and appliances throughout
  • 2 King-sized Master suites with en-suite bathrooms and private balconies with Gulf views
  • 2 Kings, 1 Queen and 2 Twins
  • Private heated pool with tropical landscaping
  • Fully stocked gourmet kitchen
  • 5 LG Smart TV's, 40 Megabit Internet, X-Box gaming system and outdoor Bose speakers around the pool
Book now
Castaway Cove
From $2012 to $6957 per week
  • Located on the prestigious North-end
  • 4 bedrooms and 2.5 bathrooms
  • 1 King, 2 Queens, 1 set of bunks-Sleeps up to 6 in beds, 8 total
  • Private salt water pool-Gas BBQ grill
  • Only 2 minutes away from the North point beaches
  • Very short walk to the popular Rod and Reel Pier
  • Large balcony overlooking the pool
  • Fully equipped modern kitchen
  • Over-sized Garage and Elevator
  • Pool table, Air Hockey, Free Weights, and Weight Bench
Book now
Island Dream
From $2100 to $6048 per week
  • On our Professional Linen Service Program
  • Beautiful high-end construction with an open floor plan living area
  • 4 Bedrooms/4 Bathrooms-Sleeps 8 in beds, 10 total
  • Private heated pool with Summer kitchen and tropical landscaped grounds
  • Exclusive North End location-Easy 2 minute walk to Bayside beach
  • Quality furnishings and linens, open floor plan in the living area, exquisite furnishings and marble throughout
  • 1 King, 2 Queens and 2 Twins
  • Flat screen TV's in all bedrooms, 3D Smart TV in living room, High-speed wireless internet, DVD and IPod sound system
  • 4 Balconies all with patio furniture
  • Large Master suite with wet room-all bedrooms have their own bathrooms
Book now
Paradise Found
From $2450 to $6489 per week
  • Direct Bay front-Gorgeous Bay water views througout
  • Private heated pool overlooking the Bay
  • Pool side lanai with a hammock and BBQ grill
  • Private boat dock
  • 4 bedrooms and 4.5 bathrooms
  • Sleeps up to 8--1 King, 1 Full, 2 Twins, 1 Twin day bed with a trundle
  • Only a 3 minute stroll to the Gulf beaches
  • Each bedroom has a balcony
  • Spacious deck with outdoor seating
Book now
Island Retreat
From $1400 to $6048 per week
  • On our Professional Linen Service Program
  • Luxury Island style home
  • Two minute stroll to the beach
  • Tropical heated pool/Tiki Bar
  • West-facing, view of the gulf
  • Two king-sized, Master en-suites with a jacuzzi tub in Master bed #1
  • Flat-screen TVs, DVD, Internet, Game room with Ping-Pong table and bonus kids area with TV and Wii
  • Large, fully-equipped kitchen-Luxury furniture throughout
  • Double garage
  • Sleeps 8 in beds, 10 total
Book now
Avalon
From $2303 to $38938 per week
  • On our Professional Linen Service Program
  • Brand new luxury 4 bedroom and 3.5 bath, only a 30 second walk to the Gulf beach
  • Sweeping views of the Gulf water
  • Luxury furniture and fixtures
  • Roof-top deck, 180 degree water views
  • Travertine marble throughout
  • Deluxe private heated pool with spa
  • HD flat screen TV's throughout, Wireless Internet
  • Sleeps 8 in beds-3 Kings, 2 twin beds
  • Gas BBQ grill, Summer kitchen by pool and elevator
Book now
White Sands
From $1540 to $4620 per week
  • On our Professional Linen Service Program
  • Newly luxury elevated 4 bedroom and 4.5 bathroom home
  • Short 5 minute walk to the beautiful Gulf-great location!
  • 4 King beds and 2 bunk beds: Sleeps 12 total
  • Private heated pool with spa and covered lanai
  • 4 beach chairs and 1 beach cart provided for guest use
  • Xbox gaming system and 6 flat screen TVs
  • 2 car garage
  • Close to local shops and restaurants
  • Professionally decorated
Book now
Ocean Breeze
From $1400 to $4066 per week
  • On our Professional Linen Service Program
  • Brand new elevated private duplex
  • 4 bedrooms and 3 bathrooms
  • 3 Kings, 1 Bunk bed--Sleeps 8 in beds
  • Private heated pool with spa, tropical landscaping, gas BBQ grill
  • Only a brisk 5 minute stroll to the Gulf beaches
  • Professionally decorated
  • 5 TV's and DVD players, Wireless Internet-Rec room with TV, Foosball and couch
  • 1 car garage
Book now
Sundown North
From $1750 to $6048 per week
  • On our Professional Linen Service Program
  • New ground-level living home
  • Private heated salt water pool
  • Multiple living areas- up & down
  • Lakefront- fishing
  • Next to Pine Ave shops/dinning
  • Short 2 minute walk to beach
  • Full deluxe kitchen
  • Flat screen HD TV throughout
  • Wireless Internet Service
Book now
Once Upon A Tide
From $2100 to $7560 per week
  • On our Professional Linen Service Program
  • Private Custom Luxury Home
  • 4 bedrooms and 3.5 bathrooms
  • 3 Queens, 2 Twins (Bunk bed)--Sleeps up to 8 in beds
  • Only a 1 minute stroll to the Gulf beaches-close to Bean Point
  • Private heated pool with tropical landscaping
  • Outdoor living room with built in grill, warming tray, refrigerator and gas fireplace
  • Ping Pong table, 4 Bikes and Xbox gaming system
  • Beach chairs and toys available for guest use
  • 2 car garage