Stays for 6+ guests in Anna Maria Island, FL
Stays for 6+ guests in Anna Maria Island, FL, from $66 a night. Book direct on each manager's site, no OTA fee.
Find stays in Anna Maria Island, FL
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Stays, best documented first
Bayou Vista Retreat
House · 3 bed · 2 bath · sleeps 6
Bradenton, FL
From $100 a night
- kitchen
- wifi
- free parking on premises
- tv
Exact location
Book direct on Anna Maria Island Vacation Homes
Dans Florida Condos Island Charm at Runaway Bay
House · 2 bed · 2 bath · sleeps 6
Bradenton Beach, FL
From $133 a night
- beach access
- kitchen
- fast wifi – 368 mbps
- dedicated workspace
Exact location
Book direct on Dan's Florida Condos
Dans Florida Condos XXXXXX at Runaway Bay
Apartment · 2 bed · 2 bath · sleeps 6
Bradenton Beach, FL
From $196 a night
- air conditioning
- bbq grill
- bathtub
- beach view
Exact location
Book direct on Dan's Florida Condos
Happy Island Cottage
House · 3 bed · 2.5 bath · sleeps 6
Holmes Beach, FL
From $265 a night
- pet friendly
- new fancy ocean wave looking metal roof
- central air
- fast wi-fi
Exact location
Book direct on Happy Island Cottage: Anna Maria Island rentals, book direct
Island Break
House · 2 bed · 2 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- beach access
- kitchen
- wifi
- free parking on premises
Exact location
Book direct on Anna Maria Island Vacation Homes
Island Interlude
House · 2 bed · 2 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- kitchen
- wifi
- free parking on premises
- shared outdoor pool - available all year
Exact location
Book direct on Anna Maria Island Vacation Homes
Sunrise On The Bay
House · 2 bed · 2 bath · sleeps 6
Bradenton Beach, FL
From $335 a night
- beach access
- kitchen
- wifi
- free parking on premises
Exact location
Book direct on Anna Maria Island Vacation Homes
Palm Breeze Getaway
Condo · 2 bed · 2 bath · sleeps 6
W Bradenton, FL
From $400 a night
- internet / wifi
- air conditioning
- central heating
- linens provided
Exact location
Book direct on Anna Maria Island Vacation Homes
Poolside Paradise
House · 3 bed · 2 bath · sleeps 10
Bradenton, FL
From $473 a night
- internet / wifi
- air conditioning
- central heating
- linens provided
Exact location
Book direct on Anna Maria Island Vacation Homes
Shore To Please
House · 4 bed · 4 bath · sleeps 8
Holmes Beach, FL
From $550 a night
- kitchen
- wifi
- free parking on premises – 4 spaces
- exterior security cameras on property
Exact location
Book direct on Anna Maria Island Vacation Homes
Sail Away
House · 4 bed · 4 bath · sleeps 8
Holmes Beach, FL
From $588 a night
- beach access
- kitchen
- wifi
- free residential garage on premises – 4
Exact location
Book direct on Anna Maria Island Vacation Homes
Anna Maria Island Beach Bay Breeze
Condo · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $119 a night
- bay view
- beach view
- gulf view
- lake view
Exact location
Book direct on Anna Maria Island Vacation Rentals
AM Island Beach To Bay Bliss
Beach house · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $120 a night
- bay view
- beach view
- gulf view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
Anna Maria Island Beach Palms 2A
Condo · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $120 a night
- bay view
- lake front
- lake view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
Anna Maria Island Beach Palms 2B
Condo · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $130 a night
- bay view
- lake front
- lake view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
Sun and Sand Getaway
House · 3 bed · 3 bath · sleeps 6
Bradenton, FL
From $131 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on .
Anna Maria Island Beach Palms 5B
Condo · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $134 a night
- bay view
- beach view
- lake front
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
L'Oasis West
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $178 a night
- dryer
- hair dryer
- hangers
- heating
City-level location
Book direct on Anna Maria Island Beach Rentals
Catching Waves
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $185 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Cozy Cabana East
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $196 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Kokomo
Cottage · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $196 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Cozy Cabana West
Bungalow · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $201 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
On Turtle Time
Cottage · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $205 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Fins Up
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $207 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Hidden Palms
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $211 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Anna Maria Aloha
Cottage · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $228 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Sandy Pants
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $242 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Mango Bay
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $252 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Vela Mar
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $261 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Tortuga Inn Beach Resort # 229 Island Condo, 2Bdrm
Condo · 2 bed · 1 bath · sleeps 6
Bradenton Beach, FL
From $265 a night
- shared heated outdoor swimming pool
- parking
- parking option included
- shared garden
Exact location
Book direct on tortugainncondo229.com
AMI Beach Home 4 BR, 201 69th St., Holmes Beach, Florida
House · 4 bed · 4 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Anna Maria Island!
AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace
Beach house · 3 bed · 2 bath · sleeps 6
Bradenton Beach
From $275 a night
- bay view
- beach front
- beach view
- gulf view
Exact location
Book direct on Anna Maria Island Vacation Rentals
Serenity Now
Loft · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $286 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Point's Hideaway
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $296 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
AMI Peppertree Paradise
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $304 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
She's Always Right
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $304 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Sol Mate
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $315 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
The Palm at Bean Point
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $324 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Coconut Lagoon
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $326 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Anna Maria Island Beach Palace
Condo · 4 bed · 3 bath · sleeps 8
Bradenton Beach
From $330 a night
- beach view
- gulf view
- lake view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
Hangin on Hammock
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $331 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
La Buena Vida
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $331 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
A Wave From It All
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $335 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Sunset at 714
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $369 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Historical home
House · 5 bed · 2 bath · sleeps 14
Bradenton, FL
From $400 a night
- fireplace
- air conditioning
- central heating
- linens provided
Exact location
Book direct on The Amazing Co-Host, Short Term Rentals
AMI Beach House 6BR, 124 50th St., Holmes Beach, Florida
House · 6 bed · 5 bath · sleeps 9
Holmes Beach, FL
From $411 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Anna Maria Island!
Sea La Vie
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $413 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Both Houses
House · 6 bed · 4 bath · sleeps 17
Bradenton, FL
From $417 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Wisconsin & Bradenton Vacation Rentals
Casa Mariposa
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $437 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Bateman's
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $490 a night
- bed linens
- clothing storage
- dryer
- elevator
City-level location
Book direct on Anna Maria Island Beach Rentals
The Curated Palm
House · 2 bed · 4 bath · sleeps 10
Anna Maria, FL
From $640 a night
- bed linens
- clothing storage
- dryer
- elevator
City-level location
Book direct on Anna Maria Island Beach Rentals
Three Little Birds
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $648 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Tern Key
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $729 a night
- bed linens
- clothing storage
- dryer
- elevator
City-level location
Book direct on Anna Maria Island Beach Rentals
Happy Ours
House · 2 bed · 3 bath · sleeps 12
Anna Maria, FL
From $762 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Just Beachy
Bungalow · 4 bed · 2 bath · sleeps 13
Bradenton
From $948 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Sea Gem
Bungalow · 4 bed · 3 bath · sleeps 10
Bradenton
From $1,173 a night
- lightning-fast wi-fi
- dedicated office space for remote work
- two spacious living rooms with smart tvs
- two laundry rooms (detergent provided)
Exact location
Book direct on BNB Breeze
Azalea Riverfront
Bungalow · 4 bed · 2 bath · sleeps 10
Bradenton
From $1,365 a night
- air conditioning
- body soap
- conditioner
- dryer
Exact location
Book direct on BNB Breeze
Canalfront Retreat, Pool, Dock & Putting Green
House · 3 bed · 2.5 bath · sleeps 8
Bradenton, FL
From $100 a night
- heated private pool & spa($100/night)
- private dock
- firepit
- outdoor patio/dining + tv
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
Beach house · 2 bed · 2 bath · sleeps 6
Longboat Key
From $101 a night
- adventure
- area
- away from it all
- bay
Exact location
Book direct on Anna Maria Island Vacation Rentals
Anna Maria Island Bridge Port Beach Resort
Condo · 2 bed · 2 bath · sleeps 6
Bradenton Beach
From $110 a night
- bay view
- beach view
- lake view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-30 08:13 UTC. Prices and facts are whatever the manager published on their own site.