Stays for 8+ guests in Anna Maria Island, FL
Stays for 8+ guests in Anna Maria Island, FL, from $89 a night. Book direct on each manager's site, no OTA fee.
Find stays in Anna Maria Island, FL
Or narrow it with the fields below. Every one is optional and an empty field is not a filter.
Other facets here
Stays, best documented first
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
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
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
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
Luxury Villa Heated Pool, Putt-Putt & Bocce
House · 4 bed · 3 bath · sleeps 10
Bradenton, FL
From $300 a night
Exact location
Book direct on StayDream Vacations
Beach Palace AMI
Condo · 4 bed · 3 bath · sleeps 8
Bradenton Beach
From $350 a night
- bay view
- beach view
- gulf view
- near ocean
Exact location
Book direct on Anna Maria Island Vacation Rentals
Bradenton Beach Club 225
Apartment · 2 bed · 2 bath · sleeps 8
Bradenton Beach, FL
From $607 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Casa Del Mar
House · 2 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $607 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Private Oasis w/ Heated Saltwater Pool & Hot Tub
House · 4 bed · 2 bath · sleeps 13
Bradenton, FL
From $700 a night
Exact location
Book direct on StayDream Vacations
Sarasota Family Home | Private Pool & Hot Tub
House · 4 bed · 2 bath · sleeps 10
Sarasota, FL
From $750 a night
- free parking
- hair dryer
- baking sheet
- fire extinguisher
Exact location
Book direct on away from Home
Surrounded by Sea Breezes
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $768 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Summer Breeze
House · 2 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $822 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Simpatico
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $834 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Kai Blue
House · 2 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $851 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Yacht Rock Ranch
House · 2 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $870 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Bean Point Residence Unit A
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $882 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Manatee Lookout
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $913 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Island Dream
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $974 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Flip Flops Forever
House · 2 bed · 2 bath · sleeps 10
Holmes Beach, FL
From $1,065 a night
Exact location
Book direct on Anna Maria Vacation Rentals
AMI 1 Block 2 Beach, Big Heated Saltwater Pool
House · 4 bed · 3 bath · sleeps 8
Anna Maria, FL
From $1,200 a night
Exact location
Book direct on StayDream Vacations
Stonehenge
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $1,339 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Anchor Splash
House · 2 bed · 2 bath · sleeps 10
Anna Maria, FL
From $1,380 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Blue Lagoon
House · 4 bed · 4 bath · sleeps 8
Anna Maria, FL
From $1,461 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Reef Romance
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $1,500 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Coconut Cove
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $1,521 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Coastal Serenity
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $1,643 a night
Exact location
Book direct on Anna Maria Vacation Rentals
It’s Miller Time
House · 4 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $1,643 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Portside Paradise
House · 3 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $1,643 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Summer Retreat
House · 3 bed · 2 bath · sleeps 12
Bradenton Beach, FL
From $1,704 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Sunset Penthouse at Bradenton Beach Club
Apartment · 2 bed · 2 bath · sleeps 10
Bradenton Beach, FL
From $1,704 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Bimini Cove
House · 2 bed · 2 bath · sleeps 12
Anna Maria, FL
From $1,740 a night
Exact location
Book direct on Anna Maria Vacation Rentals
Riverfront 3BR with screened private pool & grill
House · 3 bed · 2 bath · sleeps 8
Bradenton, FL
From $423 a night
- air conditioning
- available in the apartment: wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~ WE ARE OPEN! ~ FABULOUS POOL!! ~ FREE ELECTRIC CAR CHARGER ~
House · 3 bed · 2 bath · sleeps 8
Bradenton, FL
From $637 a night
- air conditioning
- barbecue grill
- bedsheets provided
- children's games
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Island Haven
House · 2 bed · 2 bath · sleeps 8
Holmes Beach, FL
From $973 a night
Exact location
Book direct on Anna Maria Vacation Rentals
1001 Longboat Club Road
House · 5 bed · 6 bath · sleeps 12
Longboat Key, FL
From $1,750 a night
- gated community
- private beach access with chairs and umb
- garage parking
City-level location
Book direct on Longboat Key Vacation Rentals
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
Nearby
Managers here
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.