Anna Maria Rentals
From $926 per night (USD)VRBO
Costa Bella: 4-Bedroom Home with Private Pool and Spa / Close to Beach and Pine
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Costa Bella by Anna Maria Island Accommodations Welcome to Costa Bella, a four bedroom, four and a half bath luxury va ...
From $926 per night (USD)VRBO
From $437 per night (USD)VRBO
Lakeview Lookout - Canal Front Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this charming 2-bed cottage on Anna Maria Island’s north end, sleeping 5. Enjoy canal views, a king bedroom wi ...
From $437 per night (USD)VRBO
From $510 per night (USD)VRBO
Private Pool - Fern Cottage by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fern Cottage, an exquisite elevated beach house located in the highly sought-after residential north end of A ...
From $510 per night (USD)VRBO
From $1106 per night (USD)Expedia
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover your slice of paradise in this beautifully updated Spanish-style beach house, Mimosa Bay, perfectly perched on ...
From $1106 per night (USD)Expedia
From $374 per night (USD)VRBO
Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are excited to announce that our popular Island rental is back on the market! It has been undergoing a complete remod ...
From $374 per night (USD)VRBO
From $549 per night (USD)Expedia
Blue Osprey: 2 Blocks to Beach, Pool, Spa, Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Osprey by Anna Maria Life Vacation Rentals 111 Los Cedros, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $549 per night (USD)Expedia
From $360 per night (USD)VRBO
Bayfront Escape Dog-Friendly Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bay Cottage by AMI Locals VR25-000013 Welcome to Bay Cottage, a charming ground level waterfront duplex nestled along ...
From $360 per night (USD)VRBO
From $578 per night (USD)Expedia
Waterfront Home! Perfect for Large Groups or Families! – Dock of the Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dock of the Bay by AMI Locals VR16-000039 Welcome to Dock of the Bay, a stunning waterfront duplex located on beauti ...
From $578 per night (USD)Expedia
From $675 per night (USD)VRBO
Heated Plunge Pool & Screened Lanai: 2BR/2BA Oasis Steps from North-End Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your perfect Anna Maria Island hideaway in this bright and breezy 2-bedroom, 2-bath home—complete with a queen ...
From $675 per night (USD)VRBO
From $1143 per night (USD)Expedia
Luxury Beachfront Home! Steps to Beach and Shopping and Sweeping Bay Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
ANNA MARIA- SHORE IS PARADISE LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features ...
From $1143 per night (USD)Expedia
From $766 per night (USD)VRBO
Sun and Spring by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sun and Spring is a brand-new luxury retreat on Anna Maria Island, offering refined coastal elegance just steps from Pin ...
From $766 per night (USD)VRBO
From $731 per night (USD)Expedia
Beach Days, Flocktail Nights & Island Memories
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Property Highlights • Just a short walk to the beach and Pine Avenue • Fire pit perfect for evening gatherings • Outd ...
From $731 per night (USD)Expedia
From $557 per night (USD)VRBO
Moon Shadow South - Bean Point 3bed - Powered by Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Moon Shadow South, a beautifully appointed 3-bedroom, 2-bathroom custom home on Anna Maria Island, where coas ...
From $557 per night (USD)VRBO
From $609 per night (USD)Expedia
Cozy Barefoot Bungalow: Steps to Bayfront Park & Bean Point, Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Barefoot Bungalow, a ground-level hideaway recently updated in early 2025. The open-concept living area welco ...
From $609 per night (USD)Expedia
From $1124 per night (USD)VRBO
Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Tortuga Bay is a canalfront 5BR/3BA escape just a 2-minute walk to the beach 🏖️! Enjoy a private pool with sp ...
From $1124 per night (USD)VRBO
From $1295 per night (USD)Expedia
Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Seaside Magnolia is a luxury island retreat just 3 blocks from the beach and steps to Pine Ave 🌴🏖️. Enjoy a ...
From $1295 per night (USD)Expedia
From $715 per night (USD)VRBO
Paradise on Pine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Paradise on Pine – a stylish island retreat perfectly situated in the heart of Anna Maria! This charming 3-be ...
From $715 per night (USD)VRBO
From $1194 per night (USD)Expedia
Bleuphoria! Rooftop Views and Poolside Fun!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bleuphoria by AMI Locals Welcome to Bleuphoria, a four-bedroom, four-bath luxury beach home on the peaceful North End ...
From $1194 per night (USD)Expedia
From $500 per night (USD)VRBO
Welcome to Island Sea-Cret!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Sea-Cret by Anna Maria Vacations Home in Anna Maria, FL Welcome to Island Sea-Cret by Anna Maria Vacations, a ...
From $500 per night (USD)VRBO
From $884 per night (USD)Expedia
OASIS~2min walk to Gulf,3 King+Twin Bunk,Salt Pool+Spa,Golf,Bikes,Bocce+Cornhole
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience an unforgettable vacation at Key Lime House! This chic Bahamian-inspired property sits at the coveted north e ...
From $884 per night (USD)Expedia
From $363 per night (USD)VRBO
McBean Point: Dog Friendly! Walk to Bean Point! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
McBean Point by Anna Maria Life Vacation Rentals 795 Jacaranda Rd, Unit A, Anna Maria, FL 34216 What You'll Love About ...
From $363 per night (USD)VRBO
From $692 per night (USD)Expedia
Bold Luxury Retro 3BR Oasis w/ Huge Heated Pool & Family Suite
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Mary Ann of Anna Maria, a single-story oasis where contemporary luxury meets retro charm. Sleek white walls s ...
From $692 per night (USD)Expedia
From $629 per night (USD)VRBO
Key Lime Cottage | Hot Tub | Steps to Beach | Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Key Lime Cottage is a charming 3BR/2BA coastal retreat just across the street from the Gulf beach and two hous ...
From $629 per night (USD)VRBO
From $529 per night (USD)Expedia
Duplex Retreat with 2 Kitchens, Lanai and Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A Place in Paradise Retreat by Anna Maria Island Accommodations Duplex in Anna Maria, Florida Welcome to A Place in Pa ...
From $529 per night (USD)Expedia
From $581 per night (USD)VRBO
AMI Beach Hideaway by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your new favorite Anna Maria Island retreat. With its unbeatable location and fresh coastal updates, AMI Beac ...
From $581 per night (USD)VRBO
From $1051 per night (USD)Expedia
Tropical Paradise: 4BR Island Home w/ Pool & Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tucked away just steps from the calm shoreline of Bayfront Park, Tropical Paradise is your perfect home base for a relax ...
From $1051 per night (USD)Expedia
From $636 per night (USD)VRBO
Beautiful North End Canal Home, Pool, Kayaks, Dock, close to beach, beach gear
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream island escape - an elegantly remodeled, canal-front home that perfectly blends coastal charm with ...
From $636 per night (USD)VRBO
From $650 per night (USD)Expedia
Anna Maria Island Waterfront Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Spacious 3 bedroom, 2 bathroom waterfront home on Anna Maria Island with a private pool, infinity spa, canal-f ...
From $650 per night (USD)Expedia
From $584 per night (USD)VRBO
Manatee Manor by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Manatee Manor is a newly remodeled two-bedroom, two-bathroom, pool, and canal front cottage in Anna Maria. Amenities In ...
From $584 per night (USD)VRBO
From $957 per night (USD)Expedia
Duplex Heated Pool Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just a short 3-block stroll to the stunning Anna Maria Island Beach, Bayfront Park, and the charming shops and restauran ...
From $957 per night (USD)Expedia
From $758 per night (USD)VRBO
Pine Ave Private Home with Jacuzzi, Pool, & 8-hole mini golf course!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Hammock Hideaway! ⚓.02 Miles to Pine Ave. Shopping, Restaurants, and more! ⚓.03 Miles to AMI Beaches ⚓8 Ho ...
From $758 per night (USD)VRBO
From $1022 per night (USD)Expedia
Acacia Breeze by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Dock under repair!Escape to Acacia Breeze for an unforgettable Anna Maria Island getaway!There are so many areas to expl ...
From $1022 per night (USD)Expedia
From $614 per night (USD)VRBO
Sea La Vie by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea La Vie!This is the relaxing Island getaway that you have been looking for. You and the family will love s ...
From $614 per night (USD)VRBO
From $730 per night (USD)Expedia
Jersey Gal by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Jersey Gal!Experience all the great amenities of this property by renting the main house only, featuring 3 be ...
From $730 per night (USD)Expedia
From $1470 per night (USD)VRBO
Amazing AMI House! Heated pool and hot tub!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Welcome to your dream vacation rental on Anna Maria Island! This stunning home, nestled in the heart of AMI, f ...
From $1470 per night (USD)VRBO
From $739 per night (USD)Expedia
Hammock in the Sun by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hammock in the Sun!This North end home offers a prime location just steps from Pine Avenue. Indulge in deligh ...
From $739 per night (USD)Expedia
From $1046 per night (USD)VRBO
Pine Avenue next door!~Heated pool~Steps to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: AMI Oasis is a luxurious 4-bedroom retreat steps from Pine Avenue and a 5-minute walk to the beach. Enjoy a pr ...
From $1046 per night (USD)VRBO
From $2260 per night (USD)Expedia
Lazy River! Mini Golf! Sleeps 16 Anna Maria Island - Nautical Situation
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
Nestled in Anna Maria, this delightful house offers guests a tranquil and peaceful retreat. With 8 bedrooms including 7 ...
From $2260 per night (USD)Expedia
From $971 per night (USD)VRBO
Mermaid’s Purse~Private Pool! 40 steps to beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 🧜♀️ Mermaid’s Purse is a charming 2BR/2BA north-end retreat just 40 steps from Palmetto Beach—no roads to cr ...
From $971 per night (USD)VRBO
From $1176 per night (USD)Expedia
New Canal Front Beach House on AMI! Gorgeous Pool!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Discover luxury at Shell We Dance, a stunning canal-front estate on Anna Maria Island. This brand-new six-bedr ...
From $1176 per night (USD)Expedia
From $1369 per night (USD)VRBO
NEW! Meet Me At Sunset! 3 Homes from the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 🌅 Meet Me at Sunset is a 4BR/4.5BA beach-boho villa just 3 homes from the Gulf 🌊. Enjoy a heated pool & spa, ...
From $1369 per night (USD)VRBO
From $858 per night (USD)Expedia
Fun Family Home close to beach, Pool, outdoor games, beach gear
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
New to the rental inventory and awaiting your stay! This Island home is a Charming, mix of modern + vintage with man ...
From $858 per night (USD)Expedia
From $1409 per night (USD)VRBO
AMI Canal-Front Luxury • Heated Pool /Spa & Boat Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Hammock Daze — Luxury Canal-Front Retreat with Boat Dock on Anna Maria Island 12 Guests | 4 Bedrooms | 8 Beds | 4 Bath ...
From $1409 per night (USD)VRBO
From $806 per night (USD)Expedia
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Family-Friendly North End Anna Maria Island Cottage with Private Heated Pool Unwind and reconnect at A Cozy Cottage, ...
From $806 per night (USD)Expedia
From $812 per night (USD)VRBO
Beach meets Bay: Your Private Poolside Beach-Boat-Bay-Paradise
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a North End Waterfront Oasis Discover the ultimate island retreat at Poinsettia Road, a sprawling estate nestl ...
From $812 per night (USD)VRBO
From $612 per night (USD)Expedia
Gulf View Paradise - modern and spacious - Steps to beautiful Gulf Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a sanctuary on the exclusive, tranquil North End of Anna Maria Island. Following an extensive 2021 and 2024 mo ...
From $612 per night (USD)Expedia
From $544 per night (USD)VRBO
Sand Dollar Cottage - Vintage - updated - flip flop walk to best Gulf Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Ultimate Anna Maria Island Escape Experience the charm of "Old Florida" in our renovated beach cottage. Tucked away ...
From $544 per night (USD)VRBO
From $1404 per night (USD)Expedia
Elm Street Retreat - by Island Real Estate Vactions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover refined island living at Elm Street Retreat, an upscale Anna Maria Island beach rental located only steps from ...
From $1404 per night (USD)Expedia
From $1034 per night (USD)VRBO
4 King Beds + Guest House • Heated Pool/Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Pearl is a 4BR/3BA home on Anna Maria Island's quiet north end, a short walk to Pine Avenue's shops and restaurants ...
From $1034 per night (USD)VRBO
From $941 per night (USD)Expedia
The Beach Treehouse: Canal, Dock, Pool, Treehouse by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Beach Treehouse by Anna Maria Life Vacation Rentals 101 Gull Dr, Anna Maria, FL 34216 What You'll Love About This H ...
From $941 per night (USD)Expedia
From $686 per night (USD)VRBO
Tree Top Bungalow: 2-min walk to beach access, Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Tree Top Bungalow, a charming coastal retreat tucked away on beautiful Anna Maria Island just moments from th ...
From $686 per night (USD)VRBO
From $845 per night (USD)Expedia
Bella Bungalow: Ground level, on the bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wake up to breathtaking waterfront views at Bella Bungalow, a beautifully appointed 3-bedroom, 2-bath retreat nestled al ...
From $845 per night (USD)Expedia
From $1348 per night (USD)VRBO
Palmetto Paradise~Heated Pool/Spa, Steps to the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 🌴 Palmetto Paradise is a stunning multi-level luxury retreat featuring 4 ensuite bedrooms, open-concept livin ...
From $1348 per night (USD)VRBO
From $1530 per night (USD)Expedia
Palmetto Sunset -Heat Pool/Spa, Steps to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 🌴 Palmetto Sunset is a stunning multi-level luxury retreat featuring 4 ensuite bedrooms, open-concept living, ...
From $1530 per night (USD)Expedia
From $1776 per night (USD)VRBO
Bay View Beauty ~ Luxury Bayfront Retreat
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: 🌊 Bay View Beauty is a stunning 7BR/7.5BA waterfront retreat with panoramic bay views on Anna Maria Island! � ...
From $1776 per night (USD)VRBO
From $945 per night (USD)VRBO
Entire house : duplex 2 kitchens 2 bedrooms 2 bathrooms. Sleeps 6. Fenced yard.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anna Maria Bean Point Beach Cottage Vacation at Anna Maria Island with the most beautiful white sands beach and crystal ...
From $945 per night (USD)VRBO
From $2012 per night (USD)VRBO
81A - High End Luxury Retreat w/ 12' TV!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to 81A by Exclusive Vacations, a design-forward luxury retreat inspired by the iconic architecture of Florida’s ...
From $2012 per night (USD)VRBO
From $1085 per night (USD)Expedia
A Perfect Day: Gulf Front! Rooftop Deck, Putt Putt, Pool Spa by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Perfect Day by Anna Maria Life Vacation Rentals 102 Cedar Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1085 per night (USD)Expedia
From $1185 per night (USD)VRBO
Steps to Beach | SwimSpa | Elevator | Luxury
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury Beach Home • Steps to Sandbar Restaurant • Elevator • Sleeps 10 • Pets Welcome Welcome to Villa Del Sol, a luxur ...
From $1185 per night (USD)VRBO
From $635 per night (USD)Expedia
Iris-istible Options by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Iris-istible Options, your canal-front escape on Iris Street at the north end of Anna Maria Island. True to i ...
From $635 per night (USD)Expedia
From $1641 per night (USD)VRBO
White Sands:Ultra Luxury Estate Beach Block, Gulf & Bay Views by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
403 N Shore, Anna Maria, FL 34216 What You'll Love About This Home: Location! Directly on the Beach Block on the quiet n ...
From $1641 per night (USD)VRBO
From $314 per night (USD)Expedia
Cozy 2-bedroom condo with dock! Best location in Anna Maria. Beach & sunsets
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Discover this 2-bedroom condo in Anna Maria. The space features a king bed and twin beds, plus a cozy living room with a ...
From $314 per night (USD)Expedia
From $554 per night (USD)VRBO
The Fish House: Canal Front, Dock, Pool Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Fish House by Anna Maria Life Vacation Rentals 231 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $554 per night (USD)VRBO
From $894 per night (USD)Expedia
Kingfish House: Luxury Canal Home, Boat Dock, Pool, Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Kingfish House by Anna Maria Life Vacation Rentals 233 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $894 per night (USD)Expedia
From $892 per night (USD)VRBO
Mangrove Mojito - Amazing Outdoor Space!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mangrove Mojito by Anna Maria Island Accommodations Welcome to Mangrove Mojito, a recently refreshed four-bedroom, thre ...
From $892 per night (USD)VRBO
From $644 per night (USD)Expedia
Coastal Beauty - Canal Front, Dock, Pool, Spa, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Coastal Beauty by Anna Maria Life Vacation Rentals 213 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $644 per night (USD)Expedia
From $846 per night (USD)VRBO
The Gulf Lookout: A beachfront escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Gulf Lookout, a beautifully appointed 4-bedroom, 3.5-bath coastal retreat located off Oak Avenue in the c ...
From $846 per night (USD)VRBO
From $691 per night (USD)Expedia
Holly's Garden: North end canal front home steps to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Holly’s Garden, a charming 2-bedroom canal-front home located on the desirable north end of Anna Maria Island ...
From $691 per night (USD)Expedia
From $981 per night (USD)VRBO
Dolphins Delight: Rooftop deck, large heated pool, hot tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Dolphin's Delight offers four bedrooms and three and a half bathrooms of freshly designed living space within easy reach ...
From $981 per night (USD)VRBO
From $938 per night (USD)Expedia
Salty Pirate - Bayview home with a pool and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Set sail for your next island getaway at Salty Pirate, a charming 4-bedroom, 3-bath vacation home on South Bay in Anna M ...
From $938 per night (USD)Expedia
From $575 per night (USD)VRBO
Boat slip & dock Surrounded by Sea Breezes by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A few things that make Surrounded By Sea Breezes special: - Anna Maria on Anna Maria Island - 65 min walk to Gulf Beache ...
From $575 per night (USD)VRBO
From $872 per night (USD)Expedia
Luxury Family Getaway w/ Pool, Putting and Backyard Fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Magnolia Palms – A Private Backyard Retreat Near the Beach Welcome to Magnolia Palms, where thoughtful luxury meets rel ...
From $872 per night (USD)Expedia
From $672 per night (USD)VRBO
The Pink Palm - Recently Refreshed
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Pink Palm by AMI Locals Welcome to The Pink Palm, a recently refreshed three-bedroom, three-bath Anna Maria Island ...
From $672 per night (USD)VRBO
From $1086 per night (USD)Expedia
Luxury Beach Home | Steps From AMI Beachs | Heated Pool
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Luxury Beach Home • Gulf Views • Heated Pool • Steps to Beach • Sleeps 10 Welcome to Sunset Paradise, a stunning Anna M ...
From $1086 per night (USD)Expedia
From $739 per night (USD)VRBO
Tamatoa - Upscale Three Bedroom!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Tamatoa by AMI Locals Tamatoa is an upscale three-bedroom, three and a half-bath vacation home located in the heart of ...
From $739 per night (USD)VRBO
From $982 per night (USD)Expedia
The Lookout by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfectly positioned directly on the water, The Lookout offers a private waterfront pool, an incredible covered gazebo l ...
From $982 per night (USD)Expedia
From $1504 per night (USD)VRBO
Summer Paradise-Rooftop deck and private heated pool/spa
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summer Paradise 244 Willow Ave, Anna Maria, FL 34216 What you will love about this property: • Less than 8-minute walk t ...
From $1504 per night (USD)VRBO
From $1296 per night (USD)Expedia
Happy Ours – NEW LISTING, Direct Beachfront Home On Magnolia
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Happy Ours! On Anna Maria Island (Anna Maria, FL) JUST RELAUNCHED AS A RENTAL and UNDER NEW MANAGEMENT! Exp ...
From $1296 per night (USD)Expedia
From $894 per night (USD)VRBO
Steps to Beach - Anna Maria Island - Island Time!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to your Anna Maria Island getaway, where life moves slower and sunsets steal the show. Spend your days on one of ...
From $894 per night (USD)VRBO
From $842 per night (USD)Expedia
Tampa Bay front single family home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover one of the most affordable waterfront opportunities on the north end of Anna Maria Island, offering the perfect ...
From $842 per night (USD)Expedia
From $1110 per night (USD)VRBO
Bridge and Bay Escape - Brand New Listing!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bridge & Bay Escape is a brand-new, four-bedroom, five-bath luxury home on the peaceful north end of Anna Maria Island. ...
From $1110 per night (USD)VRBO
From $1513 per night (USD)Expedia
Waves Edge - Beachfront!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waves Edge by AMI Locals Welcome to Waves Edge, a beautifully beachfront four bedroom Anna Maria Island vacation rental ...
From $1513 per night (USD)Expedia
From $597 per night (USD)VRBO
Bridgeview: Amazing Bay Views! Roof Top Deck, Pool & Spa by Anna Maria Life
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Bridgeview by Anna Maria Life Vacation Rentals 832 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $597 per night (USD)VRBO
From $661 per night (USD)Expedia
Casa Consuelo - 4 Bedroom Home Steps from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the perfect beach getaway in this affordable 4-bedroom, 2-bath home located on the desirable north end—just one ...
From $661 per night (USD)Expedia
From $773 per night (USD)VRBO
Beach Baby/ 4 Min Walk to The Bean Point Beach/Private Heated Pool/HotTub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Slip into island time at Beach Baby, a bright and breezy two-bedroom retreat just a short stroll (only six houses!) from ...
From $773 per night (USD)VRBO
From $423 per night (USD)Expedia
Salty Margarita by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Make a salty margarita as soon as you arrive at Salty Margarita, a beautifully renovated 2-bedroom, 3-bathroom single-fa ...
From $423 per night (USD)Expedia
From $753 per night (USD)VRBO
Sweet Retreat Cottage: Ground level cottage across the street from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This Anna Maria Island rental was given the name Sweet Retreat Cottage for a reason. Offering a private heated pool, vie ...
From $753 per night (USD)VRBO
From $706 per night (USD)Expedia
Zen Beach Cottage: Beautiful ground level home steps to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Skilled craftsmanship, a tranquil atmosphere, and an unbeatable location come together at the Zen Beach Cottage, a three ...
From $706 per night (USD)Expedia
From $862 per night (USD)VRBO
Prana Sanctuary: Luxury 4 Bedroom Home in Heart of Anna Maria
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tucked away on the coveted north end of Anna Maria Island, this stunning 4-bedroom, 4.5-bathroom pool home on Pine Avenu ...
From $862 per night (USD)VRBO
From $984 per night (USD)VRBO
New AMI Retreat | Private Pool | Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Sunlit Shores, a beautifully designed luxury retreat in the heart of Anna Maria Island. This newly built 3-be ...
From $984 per night (USD)VRBO
From $286 per night (USD)VRBO
Ground-floor 2BR coastal retreat. Sunny great room-Garden patio-1 block to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sun-Drenched Anna Maria Escape. Spacious Ground-floor 2BR coastal retreat. Big sunny great room: big yard and lush garde ...
From $286 per night (USD)VRBO
From $1030 per night (USD)Expedia
Pool/Spa - Reef Romance by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A few things that make Reef Romance special: - Concierge Collection Property - Golf cart included! - Three houses from b ...
From $1030 per night (USD)Expedia
From $570 per night (USD)VRBO
Canal Front, Bay Breeze Bungalow by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A few things that make Bay Breeze Bungalow special: - North end of Anna Maria - private home on cul-de-sac - Pool (not h ...
From $570 per night (USD)VRBO
From $1478 per night (USD)Expedia
Poolest House on the Island by Duncan Real Estate
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Poolest House on the Island! This beautiful, North-end 5-bedroom, 4 1/2-bathroom pool home has 3270 sqare fee ...
From $1478 per night (USD)Expedia
From $691 per night (USD)VRBO
Aloha House: Beautiful North End pool home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tucked away on the coveted north end of Anna Maria Island, this charming 2-bedroom, 2-bathroom home offers the perfect b ...
From $691 per night (USD)VRBO
From $1074 per night (USD)Expedia
NEW! Waterfront + Sauna + Pool + Pet Friendly +Gym
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Elevated coastal living on Anna Maria Island. This canal-front 4BR/4BA estate sleeps 10 across two king master ...
From $1074 per night (USD)Expedia
From $318 per night (USD)VRBO
C Glass Cottage Adorable Bungalow close to Pine Ave, Bay and Pier
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
C Glass Cottage 520 Spring Ave Unit C, Anna Maria, FL 34216 Welcome to "C Glass Cottage", a two-bedroom, one-bath ground ...
From $318 per night (USD)VRBO
From $2343 per night (USD)Expedia
Moondance - Steps to the beach! Heated pool!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: 🌙 Moondance is a luxury 6BR/6.5BA beach-block retreat just two homes from the Gulf 🌊. Enjoy stunning Gulf vi ...
From $2343 per night (USD)Expedia
From $1732 per night (USD)VRBO
Elegance~Gorgeous! Arcade!~ Heated pool/spa~North End!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: Elegance is a brand-new 7-bedroom, 7-bath luxury retreat on Anna Maria Island’s North End, just two blocks fro ...
From $1732 per night (USD)VRBO
From $1520 per night (USD)Expedia
Villa La Concha~West of Gulf Steps to the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: 🌴✨ Welcome to Villa La Concha ✨🌴 Just one minute (only 7 houses!) from the sugar-white sands of Anna Maria ...
From $1520 per night (USD)Expedia