Anna Maria Rentals
From $559 per night (USD)VRBO
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2 Bath with private pool, maximum occupancy of 6 people.
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Distanc ...
From $559 per night (USD)VRBO
From $718 per night (USD)Expedia
Havana Cay- Adorable 3 bedroom cottage style- Pool/spa and only 4 houses from be
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Havana Cay 109 Cedar Ave, Anna Maria, FL 34216 What you will love about this property: • Historic 1924 Latin style home ...
From $718 per night (USD)Expedia
From $524 per night (USD)VRBO
Bliss by the Beach by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy beachside bliss in this delightful home on the secluded and desirable North end of Anna Maria near Bean Point! * ...
From $524 per night (USD)VRBO
From $1351 per night (USD)Expedia
Island Escape! Pool, Spa, Ping Pong and Fire Pit for Group Fun
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Sail Away by AMI Locals VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front ...
From $1351 per night (USD)Expedia
From $435 per night (USD)VRBO
Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to Dock your Boat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Pelican Point is a 3-bedroom, 3-bath canal-front home designed for a relaxed Florida vac ...
From $435 per night (USD)VRBO
From $914 per night (USD)VRBO
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach chic meets casual elegance in this brand new ground level cottage only steps away from the best beach on Anna Mari ...
From $914 per night (USD)VRBO
From $856 per night (USD)VRBO
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Dreamin By Anchor Down Vacation Rentals Wake up to open water and views of the Sunshine Skyway Bridge from your own ...
From $856 per night (USD)VRBO
From $1408 per night (USD)Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Photos Updated September 2025*** Experience the ultimate waterfront getaway at this stunning bayfront property in Ann ...
From $1408 per night (USD)Expedia
From $856 per night (USD)VRBO
Beach Bay Serenity: Pine Ave canal front pool home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Beach Bay Serenity! This gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect p ...
From $856 per night (USD)VRBO
From $669 per night (USD)VRBO
Steps to Beach Access, Bean Point 3-4 Bdr Mother-in-law Site Option Downstairs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coco-Nut's of Anna Maria Island is the upstairs of a beautiful 3 bedroom, 2 bath home steps from the pristine white sand ...
From $669 per night (USD)VRBO
From $466 per night (USD)VRBO
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) The Space Step inside The Cottage on Pine and fee ...
From $466 per night (USD)VRBO
From $989 per night (USD)Expedia
Summer Breeze - 5BR Anna Maria City Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Ready to fall in love with your new vacation home, then look no further than “Summer Breeze”. This elevated beach home i ...
From $989 per night (USD)Expedia
From $282 per night (USD)VRBO
Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cute and cozy villa is aptly named "Gladiolus Hideaway"! Recently remodeled, this stylish yet comfy hideaway is t ...
From $282 per night (USD)VRBO
From $290 per night (USD)Expedia
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful ...
From $290 per night (USD)Expedia
From $724 per night (USD)VRBO
2nd House from the Beach with No Roads to Cross
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads ...
From $724 per night (USD)VRBO
From $541 per night (USD)Expedia
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with L ...
From $541 per night (USD)Expedia
From $732 per night (USD)VRBO
Pool*Hot Tub*Tiki Bar*Pickleball Court*Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Modern southern style and comfort await you at Conch Shell: A resort-like property on Bimini Bay. Meandering walkways ta ...
From $732 per night (USD)VRBO
From $530 per night (USD)Expedia
Bay Breeze Cottages #3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $530 per night (USD)Expedia
From $819 per night (USD)VRBO
Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool/Spa |
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay Breeze is a gorgeous canal front home with an expansive outdoor living area and is conveniently located close ...
From $819 per night (USD)VRBO
From $941 per night (USD)Expedia
Hogfish: Stunning Southern-style large family home, minutes from Tampa Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! Hogfish is a spacious 4 bedroom, 3 ½ bath home within walking distance to Pine Avenue, Ci ...
From $941 per night (USD)Expedia
From $445 per night (USD)VRBO
Bay Breeze Cottages #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $445 per night (USD)VRBO
From $598 per night (USD)Expedia
AMI Peppertree Paradise – Steps to Beach, Pool & Outdoor Oasis Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL) Experience AMI Peppertree Paradise — a light- ...
From $598 per night (USD)Expedia
From $636 per night (USD)VRBO
Private Dock - Manatee Lookout by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of ...
From $636 per night (USD)VRBO
From $346 per night (USD)Expedia
Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $346 per night (USD)Expedia
From $426 per night (USD)VRBO
Sea Spray 4: *Heated Pool *Pet-Friendly *Steps to beach *Shops, dining close
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*** Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of Units located in the North End of Anna ...
From $426 per night (USD)VRBO
From $2520 per night (USD)Expedia
Sundowner Beach: Luxury Gulf-front, stunning views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Sundowner Beach! This luxury gulf-front property offers everything you need to enjoy the perfect beach getaw ...
From $2520 per night (USD)Expedia
From $429 per night (USD)VRBO
Sea Spray 1: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $429 per night (USD)VRBO
From $346 per night (USD)Expedia
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $346 per night (USD)Expedia
From $797 per night (USD)VRBO
North Shore Very Walkable to Ami fun
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only ...
From $797 per night (USD)VRBO
From $511 per night (USD)Expedia
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
AMI Retreat by Anna Maria Life Vacation Rentals 746 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $511 per night (USD)Expedia
From $713 per night (USD)VRBO
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lazy Lagoon by Anna Maria Life Vacation Rentals 220 Chilson Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $713 per night (USD)VRBO
From $1732 per night (USD)Expedia
Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the G ...
From $1732 per night (USD)Expedia
From $756 per night (USD)VRBO
Glad Tidings: Heated pool, turfed outdoor lounge and dining area.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Photos updated March 2025! Welcome to Glad Tidings, a comfortable and well-appointed vacation home on Anna Maria Island ...
From $756 per night (USD)VRBO
From $243 per night (USD)Expedia
Perfect modern cottage, short walk to the beach, outdoor deck, beach gear!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Canary Cottage has 2 bedrooms and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- Thi ...
From $243 per night (USD)Expedia
From $1047 per night (USD)VRBO
FantaSea | Beachfront | Heated Pool | Golf Cart | Volleyball Court
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backy ...
From $1047 per night (USD)VRBO
From $459 per night (USD)Expedia
Charming Island Escape with Private Pool and Screened Lanai!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sweet Melissa’s Beach House by AMI Locals VR19-000057 Welcome to Sweet Melissa’s Beach House, a cheerful and welcomin ...
From $459 per night (USD)Expedia
From $765 per night (USD)VRBO
Pete's Blue Heaven: Steps to beach w/heated pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Plan your next island vacation at this exception 4 bedroom, 2 bath home located at the north end of Anna Maria! Enjoy th ...
From $765 per night (USD)VRBO
From $512 per night (USD)Expedia
Luxury bungalow with pool and spa! Canal front with dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bamboo Bungalow by AMI Locals VR19-000043 Welcome to Bamboo Bungalow by AMI Locals, a beautiful three-bedroom, two-b ...
From $512 per night (USD)Expedia
From $432 per night (USD)VRBO
Bon Ami: North End AMI, Pool Home, Short Walk to Bean Point by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bon Ami by Anna Maria Life Vacation Rentals 804 North Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: ...
From $432 per night (USD)VRBO
From $239 per night (USD)Expedia
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cute as a bug bungalow on Anna Maria's lovely north end. A block from City Pier and Tampa Bay and only four blocks to th ...
From $239 per night (USD)Expedia
From $309 per night (USD)VRBO
Anna Cabana A: North End Pool Home, Short Walk To Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Cabana A by Anna Maria Life Vacation Rentals 770 Jacaranda Rd., Anna Maria, FL 34216 What you'll love about this h ...
From $309 per night (USD)VRBO
From $323 per night (USD)VRBO
Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Voted a Tropical paradise perched among native banyon trees. Wake to the sound of sea birds in this tropical paradise. P ...
From $323 per night (USD)VRBO
From $678 per night (USD)VRBO
The Beach House 2 by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Beach House 2! Amenities Include: - Bedroom 1 King Ensuite - Bedroom 2 Queen - Queen Sleeper - Bathr ...
From $678 per night (USD)VRBO
From $465 per night (USD)Expedia
Aloha Fern: North End Beach House, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Aloha Fern by Anna Maria Life Vacation Rentals 702 Fern, Anna Maria, FL 34216 What You'll Love About This Home: Locatio ...
From $465 per night (USD)Expedia
From $1784 per night (USD)VRBO
Beaches and Dreams: Ultimate Luxury Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams, where stunning panoramic bay view ...
From $1784 per night (USD)VRBO
From $649 per night (USD)Expedia
Beautiful North end Pool Home with Gulf Views, Heated pool, steps to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are excited to announce that our popular vacation rental is back on the market after a complete renovation! Everythin ...
From $649 per night (USD)Expedia
From $872 per night (USD)VRBO
Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Buttonwood Cottage by AMI Locals Welcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home ...
From $872 per night (USD)VRBO
From $602 per night (USD)Expedia
Point's Hideaway - Luxury Retreat w/ Private Pool & Deck, Stunning Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Point's Hideaway! On Anna Maria Island (Anna Maria, FL) Please note: The home is next to a construction site. ...
From $602 per night (USD)Expedia
From $634 per night (USD)VRBO
Luxurious Island Retreat with Pool, Spa and Private Suite
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Freckled Fin by AMI Locals VR19-000006 Welcome to Freckled Fin, a vibrant and luxurious four-bedroom, four-and-a-half ...
From $634 per night (USD)VRBO
From $1144 per night (USD)Expedia
Serendipity Gulfront | Hot Tub | Heated Pool | Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity G ...
From $1144 per night (USD)Expedia
From $1144 per night (USD)VRBO
Tripletail | Beachfront | Pool & Spa | 4 King Beds
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home ...
From $1144 per night (USD)VRBO
From $740 per night (USD)Expedia
Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Sand Castle located just a few steps from the Gulf beaches of Anna Maria Island. Built in 1924, the Castl ...
From $740 per night (USD)Expedia
From $402 per night (USD)VRBO
Starfish Cottage - sleeps 4, with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Starfish Cottage is situated towards the top end of Anna Maria Island. The property is extremely well furnished and equi ...
From $402 per night (USD)VRBO
From $577 per night (USD)Expedia
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open for business in 2025! Check out the latest review. OHasis Getaway is a true oasis on both the outside and inside! ...
From $577 per night (USD)Expedia
From $1267 per night (USD)VRBO
Vitamin Sea managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
☀️ Vitamin Sea by Beach Retreats Vacation Rentals 📍 146 Crescent Dr, Anna Maria, FL 34216 Welcome to Vitamin Sea, a st ...
From $1267 per night (USD)VRBO
From $690 per night (USD)Expedia
La Cocolia located north end of Ami, Lagoon Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a Great Ami Getaway? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house ...
From $690 per night (USD)Expedia
From $1778 per night (USD)VRBO
Gulf Shore Retreat: Private Pool managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
NO CANCELLATION FEES: $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before ...
From $1778 per night (USD)VRBO
From $860 per night (USD)Expedia
Casa Mariposa – AMI Luxury Retreat Steps to Beach & Pine Ave w/ Pool & Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Mariposa! On Anna Maria Island (Anna Maria, FL) Experience Casa Mariposa where the rhythm of island lif ...
From $860 per night (USD)Expedia
From $1060 per night (USD)VRBO
Batemans – AMI Canal-Front Luxury Home w/ Pool & Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bateman's! On Anna Maria Island (Anna Maria, FL) Experience Bateman's — where thoughtful design and waterfro ...
From $1060 per night (USD)VRBO
From $405 per night (USD)Expedia
Wake up on the waters of Tampa Bay in a north Anna Maria home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story elevated beach home with gorgeous water views, steps from park and two fishing piers. Enjoy meals in the separ ...
From $405 per night (USD)Expedia
From $283 per night (USD)VRBO
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Cabana B by Anna Maria Life Vacation Rentals 301 Poinsettia Rd., Anna Maria, FL 34216 What you'll love about this ...
From $283 per night (USD)VRBO
From $752 per night (USD)Expedia
Boater's Dream! 1/2 Block from Beach- Private Boat Dock & 30' Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the Traffic: Private Waterfront Oasis on AMI’s Historic North End. Welcome to Sunshine Cottage, a beautifull ...
From $752 per night (USD)Expedia
From $459 per night (USD)VRBO
Toes in the Water: North End, West of Gulf, Steps to Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Toes in the Water by Anna Maria Life Vacation Rentals 110 Palm Ave, Anna Maria, FL 34216 What You'll Love About This Ho ...
From $459 per night (USD)VRBO
From $814 per night (USD)Expedia
Stunning Luxury Gulf Home, Private Heated Pool/Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Temp Promo: Book 7 nights or more with us by September 30, get a free 6P Bintelli Golf Cart for your stay! Normally $12 ...
From $814 per night (USD)Expedia
From $713 per night (USD)VRBO
Tucked Away in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked Away is a newly renovated custom home with everything you could possibly need for the vacation of a life time. Th ...
From $713 per night (USD)VRBO
From $835 per night (USD)Expedia
Paradise Bound! Backyard Bliss with Sun Shelf, BBQ and Coastal Decor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Paradise Bound by AMI Locals VR21-000036 Welcome to Paradise Bound, a stunning four bedroom, four bathroom vacation r ...
From $835 per night (USD)Expedia
From $825 per night (USD)VRBO
Sea Whisper: North End gem w/ pool & dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
About this space Escape to the prestigious North End of Anna Maria Island. Sea Whisper is a modern, canal-front sanctuar ...
From $825 per night (USD)VRBO
From $431 per night (USD)Expedia
Charming House with Private Heated Pool, Lanai. Great location to beach & shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
What You’ll Love About Sapphire Surf: • Location, Location, Location! Just 2 blocks to the Gulf Beach, 4 blocks to char ...
From $431 per night (USD)Expedia
From $605 per night (USD)VRBO
Gulf View Retreat! Pool, Decks and 2 King Beds!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Deckhouse by AMI Locals VR20-000007 Welcome to The Deckhouse, a beautifully remodeled three bedrooms, three bathr ...
From $605 per night (USD)VRBO
From $1242 per night (USD)Expedia
Banyan Manor! Canalfront Home with Pool, Spa, Dock and Game Room
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Banyan Manor by Anna Maria Island Accommodations VR20-000064 Welcome to Banyan Manor, a stunning canal front vacation ...
From $1242 per night (USD)Expedia
From $527 per night (USD)VRBO
Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Carefree Cay by Anna Maria Island Accommodations VR16-000412 Welcome to Carefree Cay, a three-bedroom, two-and-a-ha ...
From $527 per night (USD)VRBO
From $1309 per night (USD)Expedia
Private Luxury Home 1.5 Blocks to Beach! Heated Pool and Hot Tub!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
SeaLuxe by Anna Maria Island Accommodations VR19-000031 Welcome to SeaLuxe, a luxury four-bedroom, four full bath, an ...
From $1309 per night (USD)Expedia
From $607 per night (USD)VRBO
Canalfront Home with Pool, Dock and Putting Green! Close to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lavender Lagoon by Anna Maria Island Accommodations VR22-000006 Welcome to Lavender Lagoon, a beautiful canal front t ...
From $607 per night (USD)VRBO
From $1047 per night (USD)Expedia
Island Retreat! Pool, Games and Gulf Access!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Pelican Paradise by Anna Maria Island Accommodations VR19-000001 Welcome to Pelican Paradise, your dream getaway just ...
From $1047 per night (USD)Expedia
From $720 per night (USD)VRBO
Home with Pool and Outdoor Amenities near the Bay and Beach - North End Chic
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
North End Chic by Anna Maria Island Accommodations VR16-000361 Welcome to North End Chic, a stylish ground level vaca ...
From $720 per night (USD)VRBO
From $453 per night (USD)Expedia
AMI Escape! 2 King Suites, Twin Room and Private Pool Near Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Azure by Anna Maria Island Accommodations Home in Anna Maria, Florida VR18-000114 Welcome to Azure, a modern three be ...
From $453 per night (USD)Expedia
From $850 per night (USD)VRBO
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beachcombers by AMI Locals VR16-000284 Welcome to Beachcombers by AMI Locals, a three-bedroom, two-bathroom Anna Mari ...
From $850 per night (USD)VRBO
From $822 per night (USD)Expedia
Beautiful Guest House Near the Beach with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria Guest House 212 by Anna Maria Accommodations Cottage in Anna Maria, Florida Experience the relaxed charm o ...
From $822 per night (USD)Expedia
From $443 per night (USD)VRBO
Cozy Pine Ave Cottage Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Anna Maria Guest House 317 by Anna Maria Island Accommodations Cottage in Anna Maria, Florida Welcome to Anna Maria G ...
From $443 per night (USD)VRBO
From $812 per night (USD)Expedia
Hammock Dreams - Canal Home with Pool and Dock Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hammock Dreams by Anna Maria Island Accommodations VR16-000408 Welcome to Hammock Dreams, a beautiful three-bedroom, ...
From $812 per night (USD)Expedia
From $553 per night (USD)VRBO
Covey Cottage! Walk to Beach, Boutique Shops and City Pier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Covey Cottage by Anna Maria Island Accommodations VR16-000292 Welcome to Covey Cottage by Anna Maria Island Accommoda ...
From $553 per night (USD)VRBO
From $867 per night (USD)Expedia
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Little Pink Houses by Anna Maria Island Accommodations VR18-000136 Welcome to Little Pink Houses, a charming Anna Mar ...
From $867 per night (USD)Expedia
From $639 per night (USD)VRBO
Triple Play! Canal, Pool and Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Triple Play by Anna Maria Island Accommodations VR16-000416 Welcome to Triple Play, a canal-front 3-bedroom, 3-bath v ...
From $639 per night (USD)VRBO
From $431 per night (USD)Expedia
AMI Stay! Family-Friendly Home with Pool, Twin Room and Garden Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pink Palm Bungalow by Anna Maria Island Accommodations VR16-000353 Welcome to Pink Palm Bungalow, a charming three be ...
From $431 per night (USD)Expedia
From $1800 per night (USD)VRBO
Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dolphin Pointe by Anna Maria Island Accommodations VR16-000318 Welcome to Dolphin Pointe, a beautifully renovated nor ...
From $1800 per night (USD)VRBO
From $848 per night (USD)Expedia
Beautiful Condo on Pine Ave, 2 Blocks to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
High Tide Haven by Anna Maria Island Accommodations Welcome to High Tide Haven, a newly renovated three-bedroom, two-b ...
From $848 per night (USD)Expedia
From $841 per night (USD)VRBO
Adorable Cottage with Covered Balconies and Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Social Nest by Anna Maria Island Accommodations Welcome to Social Nest, a charming three-bedroom, two-bath vacation ho ...
From $841 per night (USD)VRBO
From $710 per night (USD)Expedia
Spacious Canal front Home with Pool, Perfect For Family Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gypsy Sol by Anna Maria Island Accommodations VR18-000034 Welcome to Gypsy Sol, your ultimate Anna Maria Island esca ...
From $710 per night (USD)Expedia
From $943 per night (USD)VRBO
Called in Sic! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Called in Sic by Anna Maria Island Accommodations VR18-000103 Welcome to Called in Sic, a stunning and newly renovate ...
From $943 per night (USD)VRBO
From $289 per night (USD)Expedia
Steps to Beach and Pool! Cozy Island Flat Near Pine Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 113 B by Anna Maria Island Accommodations VR16-000423 Welcome to Sand and Sea 113 B, a cozy two-bedroom, ...
From $289 per night (USD)Expedia
From $1211 per night (USD)VRBO
Luxury Retreat! Pool, Spa and Walk to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Water Colors by Anna Maria Island Accommodations VR18-000060 Welcome to Water Colors, a stunning four-bedroom, four-b ...
From $1211 per night (USD)VRBO
From $1063 per night (USD)Expedia
Private Home 1 Block to Beach with Pool and Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach You To It by Anna Maria Island Accommodations VR18-000150 Welcome to Beach You To It, a breezy three-bedroom, t ...
From $1063 per night (USD)Expedia
From $738 per night (USD)VRBO
Anna Maria Friends Getaway: Private Pool Close to the Beach - Coral Kai
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Kai by Anna Maria Island Accommodations VR20-000067 Welcome to Coral Kai, a three-bedroom, three-and-a-half-bat ...
From $738 per night (USD)VRBO
From $505 per night (USD)Expedia
Island Retreat with Pool and Putting Green!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Lady From the Sea by Anna Maria Island Accommodations VR18-000156 Welcome to Lady from the Sea, a coastal enchanted ...
From $505 per night (USD)Expedia
From $982 per night (USD)VRBO
Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Hurricane House by Anna Maria Island Accommodations VR16-000396 Welcome to Hurricane House, a beautifully remodeled ...
From $982 per night (USD)VRBO
From $324 per night (USD)Expedia
Sand and Sea! Relaxing Patio, Shared Pool and Walkable Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 113 A by Anna Maria Island Accommodations VR16-000423 Welcome to Sand and Sea 113 A, a charming two-bedr ...
From $324 per night (USD)Expedia
From $485 per night (USD)VRBO
Casa Allegria: Remodeled Home with Private Pool, Just Over a Block to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Allegria by Anna Maria Island Accommodations VR16-000015 Welcome to Casa Allegria, a charming three-bedroom, t ...
From $485 per night (USD)VRBO
From $302 per night (USD)Expedia
Sand and Sea 109 A! Pool, Patio and Coastal Charm!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 109 A by Anna Maria Island Accommodations VR16-000422 Welcome to Sand and Sea 109 A, a charming two-bedr ...
From $302 per night (USD)Expedia
From $997 per night (USD)VRBO
Canal Home with Private Pool and Dock - North End Zen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
North End Zen by Anna Maria Island Accommodations VR16-000360 Welcome to North End Zen, a newly renovated four-bedroo ...
From $997 per night (USD)VRBO
From $394 per night (USD)Expedia
Beautiful Home Directly Across the Street from the Gorgeous Bay!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shore's Nice by Anna Maria Island Accommodations VR21-000020 Experience your ultimate Florida escape at Shore's Ni ...
From $394 per night (USD)Expedia