Anna Maria Rentals
- From $666 per night (USD)
VRBO
Salty C Cottage Spectacular canal front home with pool and hot tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous and recently remodeled 4 bedroom, 3 1/2 bath ground level home with amazing designer touches and finishes throu ...
From $666 per night (USD)VRBO
- Click For Pricing
Expedia
Newly updated 1 bd poolside condo - perfect for your winter getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kitchen and Dining area, Living Room, Lanai with direct shared pool access Highlights: -Completely updated with all new ...
Click For PricingExpedia
- Click For Pricing
VRBO
Magnificent Resort Sixty-Six, 1 Bedroom Suite, Not Far From Your Luscious Grills & Bars
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingVRBO
- From $244 per night (USD)
Expedia
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $244 per night (USD)Expedia
- From $337 per night (USD)
VRBO
Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC# 19-000218 Cozy 'Day' Side Cottage is located in Holmes Beach on Anna Maria Island. It offers 2 bedrooms and 1 1/2 ...
From $337 per night (USD)VRBO
- From $304 per night (USD)
Expedia
Vibrant Island Home w\/ Pool, 1 Block to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A tropical paradise awaits when you book this stylish Anna Maria retreat! Ideally situated just 0.1 miles from the gorge ...
From $304 per night (USD)Expedia
- From $895 per night (USD)
VRBO
1 Block to the Beach - LARGE Private Pool - Newly Renovated 6 Bdrm Luxury House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Holmes Beach House For Rent - Luxury Vacation Rental on Anna Maria Island, Florida *All New Flooring, New Bathrooms (3 ...
From $895 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Perfect Family Vacation home, private pool - so Close to BEACH!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beach Time AMI by AMI Locals Home in Holmes Beach, Florida VRC19-000030 Welcome to Beach Time AMI! This five bedroom, ...
From $315 per night (USD)Expedia
- From $383 per night (USD)
VRBO
A Bay From It All: Private backyard oasis, steps to Bay, Bean Point
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Leave the stress of everyday life and get "A Bay From it All"! This amazing 3 bedroom / 3 full bathroom home on the cove ...
From $383 per night (USD)VRBO
- From $532 per night (USD)
Expedia
Jungalow Bay by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian para ...
From $532 per night (USD)Expedia
- From $300 per night (USD)
VRBO
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
MI Oasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are i ...
From $300 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa East is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $228 per night (USD)Expedia
- From $4785 per night (USD)
VRBO
The Rod and Reel Resort
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the new and luxurious Rod and Reel Resort. We are pleased to offer our guests the finest and most inclusive e ...
From $4785 per night (USD)VRBO
- From $261 per night (USD)
Expedia
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Pe ...
From $261 per night (USD)Expedia
- From $481 per night (USD)
VRBO
Luxury Home with Pool and Dock for Fishing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Pelican's Nest by AMI Locals Home in Anna Maria, FL Features: • Private Pool • Gorgeous Brand New Construction home • ...
From $481 per night (USD)VRBO
- From $1100 per night (USD)
VRBO
Spectacular Beachfront House with Pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 'Sky way view', one of the most exclusive homes on Anna Maria Island. It is located in one of the most specta ...
From $1100 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Charming 2br \/ 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1924, Sunset Cottages’ beautifully maintained woodwork coupled with updated amenities delivers an authentic Flo ...
From $325 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Top Rated Anna Maria Florida Vacation Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Our Sassy Seahorse has been rated as one of the top 15 out of 260 vacation rentals by Island Real Estate. Our 5-Star r ...
From $325 per night (USD)VRBO
- From $293 per night (USD)
VRBO
Mykonos: Beautifully updated with heated pool, moments to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come join us at Mykonos on Anna Maria Island! This beautifully decorate, two bedroom, two bathroom home has the perfect ...
From $293 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Best Location on Island - Read Our Guest Reviews!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seaside Views - Waterfront, Steps from Beach & Restaurants Best Location on Island - Read Our Guest Reviews! This wate ...
From $150 per night (USD)VRBO
- From $619 per night (USD)
VRBO
North end canal front home ,tiki hut, dock, heated pool, spa,beaches....
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. Thi ...
From $619 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Spacious 3 bedroom town home on Anna Maria Island, community pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
For your relaxing and family fun, Anna Maria Island vacation, check out this spacious beautiful 3 bedroom, 2.5 bath town ...
From $255 per night (USD)Expedia
- From $1395 per night (USD)
VRBO
Bay Happy: Luxury Home with View of Tampa Bay!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Happy is the perfect place for your next island getaway! This luxury property boasts breathtaking views of the bay, ...
From $1395 per night (USD)VRBO
- Click For Pricing
Expedia
“Sea Haven AMI\" on Spring Lake, 3 min walk to the beach, Mid-Island location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This property usually rents SATURDAY to SATURDAY*** Minimum 7 night rental. If you book for arrival on any other day, t ...
Click For PricingExpedia
- From $453 per night (USD)
VRBO
Direct Gulf Beach 3 Bed\/2Bath w\/ Heated Pool, FREE WiFi & Trolley, Great...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! If you like to be close to everything AND have the beach right out your back ...
From $453 per night (USD)VRBO
- Click For Pricing
Expedia
Quiet Nights of Quiet Stars on Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Quiet nights of quiet stars, quiet walks by quiet sea, quiet thoughts on quiet street, oh how lovely. Maximum 3 adults ...
Click For PricingExpedia
- From $514 per night (USD)
VRBO
Waterfront POOL home just Steps to Pine Ave and Beaches in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Anna Maria Beach Vacations brings you this fabulous private pool home in Anna Maria Florida. It boasts, 2 Bedroom and 2 ...
From $514 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Island Living, refreshing outdoor shower and pool , pet friendly if approved
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our vacation home is 1 1/2 blocks to either the Gulf of Mexico or Tampa Bay. We have remodeled the kitchen and added a ...
From $315 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Island Time: AMI North End, Pool, Close to City Pier & Pine Ave by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home Location! In the heart of Anna Maria, and withi ...
From $360 per night (USD)VRBO
- From $1620 per night (USD)
Expedia
Incredible luxury canal front home with lazy river style pool! -Winding Waves
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 8
Winding Waves by AMI Locals Home in Anna Maria, Florida VR20-000041 Your luxury beach vacation awaits at Winding Wav ...
From $1620 per night (USD)Expedia
- From $590 per night (USD)
VRBO
Large Heated Pool, 2 Master Bedroom Suites, Very Close to Gulf Beach.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
'South Cay' is an absolutely beautiful house in "Anna Maria", on Anna Maria Island, Florida. How close to the beach? Th ...
From $590 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Beachfront Paradise w\/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The home has a private be ...
From $450 per night (USD)Expedia
- From $100 per night (USD)
VRBO
Bayou Hideaway: 2 BR, 1 BA Condominium in Anna Maria, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great Pine Avenue location, across the street from the Anna Maria City Pier, walkable to Bayfront Park with its playgrou ...
From $100 per night (USD)VRBO
- From $648 per night (USD)
Expedia
New Home with Pool, Spa, and Rooftop Deck Views!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Hip Nautic by AMI Locals Home in Anna Maria, FL Highlights: • Modern decor with coastal hues throughout • Private poo ...
From $648 per night (USD)Expedia
- From $662 per night (USD)
VRBO
All Decked Out: North End Overlooks Tampa Bay, Pool, Amazing Views by Anna Maria Life Vacation Homes
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
509 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About This Home: Location! Overlooking Tampa Bay! 4 Blocks to AMI ...
From $662 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Coccoloba by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Coccoloba! This beautiful single-family home is located across from the sugar sand beaches in Holmes Beach. Y ...
From $554 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Gladiolus on the Water by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation get ...
From $489 per night (USD)VRBO
- From $149 per night (USD)
Expedia
Bayou Breeze | Amazing Waterfront Condo on Pine Ave with Dock and Water Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing Waterfront Condo at the North end of Anna Maria! Tucked away off of Pine Ave just before the Historic Anna Mar ...
From $149 per night (USD)Expedia
- From $930 per night (USD)
VRBO
Luxury Home with Private Pool, Putting Green, and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Yacht Sea by Anna Maria Island Accommodations Home in Anna Maria, FL Highlights • 5-minute walk from Beach • Private Po ...
From $930 per night (USD)VRBO
- From $365 per night (USD)
Expedia
Beautifully remodeled canal front home with private pool and spa!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Fish House by AMI Locals Home in Anna Maria, Florida VR19-000056 Welcome to The Fish House, a modern canal front pa ...
From $365 per night (USD)Expedia
- From $1397 per night (USD)
VRBO
Sirenia By The Sea - Putting Green\/Waterfront\/Dock\/\/Pool\/ Hot Tub\/StepstoBeach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Newly Renovated in 2023! - New putting green - New kitchen including coffee bar and wine fridge - All 5 new bathrooms - ...
From $1397 per night (USD)VRBO
- From $701 per night (USD)
Expedia
Anna Banana: 3 Houses to Beach! North End AMI! Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
501 North Shore, Anna Maria, FL 34216 What You'll Love About this Home: Location! 3 Homes to the Beach! North End of AM ...
From $701 per night (USD)Expedia
- From $800 per night (USD)
VRBO
Anna Maria Beach Serenity
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The fourth bedroom is located in the adjoining cottage. This property has a maximum occupancy of eight people includin ...
From $800 per night (USD)VRBO
- From $989 per night (USD)
VRBO
La Grande Maison - 4 Bed \/ 4 Bath Luxury Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Make your next vacation one you will never forget by booking La Grande Maison. With plenty of room for the entire family ...
From $989 per night (USD)VRBO
- From $750 per night (USD)
VRBO
H2O Bungalow by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
H2O Bungalow is a 3 bed, 3 bath stunning vacation home that is unique and unlike any others. *Features include* * Pr ...
From $750 per night (USD)VRBO
- From $598 per night (USD)
Expedia
My Mistress by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom/3 bath ground level canal home in Anna Maria is a hidden gem and walkable to all the best spots in Anna M ...
From $598 per night (USD)Expedia
- From $1019 per night (USD)
VRBO
Willow Walk: 3 Homes to Beach! West of Gulf Dr, Pool, Poolside Lounge Area by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
110 Willow Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 3 Houses to the Beach! 4 Bedrooms / 3 ...
From $1019 per night (USD)VRBO
- From $821 per night (USD)
Expedia
Sole Acqua: Luxury canal front home with pool, short walk to the Gulf!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury Anna Maria Island canalfront vacation rental, complete with heated pool, hot tub, and dock. Just a short walk to ...
From $821 per night (USD)Expedia
- From $405 per night (USD)
VRBO
Close to the beach with private pool and lanai
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Surf Side by AMI Locals Home in Anna Maria, FL Gulf beaches are just a short 3-minute walk away! Highlights: • Privat ...
From $405 per night (USD)VRBO
- From $880 per night (USD)
Expedia
Sand Trap by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool, spa and ...
From $880 per night (USD)Expedia
- From $456 per night (USD)
VRBO
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Anna Maria Island waterfront house newly renovated. The house is located on a large 75 ft wide deep water canal an ...
From $456 per night (USD)VRBO
- Click For Pricing
Expedia
Last Lap: *Luxury *Modern *Gulf View *Heated Pool *Steps to Beach!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Last Lap, located two properties from the gulf on the North End of Anna Maria Island! This home features 4 be ...
Click For PricingExpedia
- From $718 per night (USD)
VRBO
Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
749 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: Location! Bean Point Across the Street! 2 Min Wal ...
From $718 per night (USD)VRBO
- From $621 per night (USD)
Expedia
On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
811 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1 Block to Beach & Bean Point! 4 Bedroo ...
From $621 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Island Breeze: Steps to Beach, Heated Pool & Spa, Huge Verandah by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
119 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 5 Houses to the Beach! 2 Bedrooms / 2 ...
From $334 per night (USD)VRBO
- From $718 per night (USD)
Expedia
The Laguna Beach: 2 Blocks to Beach, Pool, 5 Hole Put Put, Foosball, Cornhole by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
212 Willow Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! Two Blocks to the Beach! 3 Bedrooms / ...
From $718 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Endless Summer- On Pine Ave, steps to beach & pier w\/ water view & dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOCATION IS EVERYTHING!! Endless Summer is a waterfront condo with amazing views and a private dock, perfectly located o ...
From $165 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Banyan Tree Beach House- Luxury home with private pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Banyan Tree Beach House!! If you think the photos are stunning, wait until you see this home in person and wa ...
From $800 per night (USD)Expedia
- From $1291 per night (USD)
VRBO
Luxury Villa with Rooftop Deck, Putting Green, and Pool\/Spa!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 8
Fine and Sandy by AMI Locals Home in Anna Maria, FL Located in the North End area of Anna Maria Island Highlights: • P ...
From $1291 per night (USD)VRBO
- From $213 per night (USD)
Expedia
Spacious Island Home with Lagoon-Style Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mangoes on Magnolia by Anna Maria Island Accommodations Home in Anna Maria, Florida Your island getaway awaits at Mang ...
From $213 per night (USD)Expedia
- From $840 per night (USD)
VRBO
AcquaLuxe - Exquisite 2022 Lux Canal Home w\/ Outdoor Oasis Pool, Spa, Dock, SUP, Kayaks, Fire Pit
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to AcquaLuxe! On Anna Maria Island (Anna Maria, FL) 3137 sq. ft. HIGHLIGHTS: - Open layout and spacious Kitche ...
From $840 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Shady Mango by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Shady Mango! An inviting ground-level vacation home just three blocks from the beach! With two bedrooms and t ...
From $316 per night (USD)Expedia
- From $2021 per night (USD)
VRBO
Anna Maria Serenity Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boasting a large, resort style heated outdoor pool with a hot tub, and a prime location on Anna Maria it's easy to fall ...
From $2021 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Sandy Beach Retreat - 3 bedroom on the beach with amazing views and private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Sandy Beach Retreat! You will fall in love with the beautiful beaches of Anna Maria Island as your backyard i ...
From $425 per night (USD)Expedia
- From $1203 per night (USD)
VRBO
Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
302 Spring Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 5 Min Walk to Gulf! 5 Min Walk to Bay! ...
From $1203 per night (USD)VRBO
- From $432 per night (USD)
Expedia
Maritime Memories by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Maritime Memories! This north-end 3 bedroom, 2 bath pool home is waiting for you to enjoy your next vacation ...
From $432 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Emerald Shores: 6 bedroom house, steps to the beach with Gulf Views!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Come enjoy a cozy 6-bedroom home on one of Anna Maria Island’s tranquil family beaches. Emerald Shores is a two-unit d ...
From $476 per night (USD)VRBO
- From $749 per night (USD)
Expedia
Bean Point Bliss: Pool Spa Putting Green
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bean Point Bliss by Anna Maria Life Vacation Rentals 820 N Shore, Anna Maria FL 34216 What You'll Love About This Home: ...
From $749 per night (USD)Expedia
- From $550 per night (USD)
VRBO
The Hammock House: Bright and modern pool home with outdoor living space
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The Hammock House, located on the North end of Anna Maria is a 3 bedroom, 3.5 bathroom spacious, contemporary home. The ...
From $550 per night (USD)VRBO
- From $586 per night (USD)
Expedia
H2O 360 by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Water abounds at this awesome 3 bedroom/2 bath Anna Maria Island gem with pool, hot tub and dock! *Features include* ...
From $586 per night (USD)Expedia
- From $446 per night (USD)
VRBO
Beachview Retreat: Steps to the beach, Gulf views, hot tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Beachview Retreat on Anna Maria! This conveniently located cottage is just steps away from white sandy, Gulf ...
From $446 per night (USD)VRBO
- From $101 per night (USD)
Expedia
Perfectly located near the beach and Pine Ave!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Place in Paradise Unit B by Anna Maria Island Accommodations Duplex in Anna Maria Welcome to A Place in Paradise Uni ...
From $101 per night (USD)Expedia
- From $149 per night (USD)
VRBO
Adorable duplex near the beach and Pine Ave!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Place In Paradise Unit A by AMI Accommodations Duplex in Anna Maria, FL Welcome to A Place in Paradise Unit A, island ...
From $149 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Pelican's Roost: Serene coastal retreat, in heart of Anna Maria Island life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Pelican's Roost" – your ultimate coastal retreat on Anna Maria Island! Nestled off the lively Pine Avenue, t ...
From $175 per night (USD)Expedia
- From $327 per night (USD)
VRBO
Gorgeous home with secluded backyard oasis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hunky Dory by AMI Locals Home in Anna Maria, Florida Relax with friends and family at Hunky Dory, a true piece of par ...
From $327 per night (USD)VRBO
- From $269 per night (USD)
Expedia
Perfect Island Location! Heated pool and plenty of room for the entire family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea grape trees, hibiscus bushes and palm trees surround this pretty white-roofed daffodil-colored cottage that is just ...
From $269 per night (USD)Expedia
- From $1420 per night (USD)
VRBO
No Tan Lines by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The ultimate in beach front Florida island living awaits you at No Tan Lines. *Features include* * Ultimate luxury BE ...
From $1420 per night (USD)VRBO
- From $411 per night (USD)
Expedia
Sea Jay: Canal front with dock, heated pool, lanai w\/outdoor kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Jay is a newly refreshed, canal front pool home located in the heart of Anna Maria! Enter the home through the kitch ...
From $411 per night (USD)Expedia
- From $612 per night (USD)
VRBO
Blue Palm: Luxury home, heated pool, hot tub, close to beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Blue Palm, your next vibrant home-away-from-home here in Anna Maria. Constructed in 2016 by luxury builders M ...
From $612 per night (USD)VRBO
- From $954 per night (USD)
Expedia
North end AMI close to beach heated pool golf cart
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Located at the north end of Anna Maria Island, this home offers a unique and well-appointed lifestyle. Custom handpicked ...
From $954 per night (USD)Expedia
- Click For Pricing
VRBO
Modern home with rooftop deck views!
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 8
Compass Rose by AMI Locals Home in Anna Maria, Florida Welcome to Compass Rose, an enchanting home with luxury ameniti ...
Click For PricingVRBO
- From $229 per night (USD)
Expedia
Coquina Cottage B by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coquina Cottage B! Coquina Cottage B is exceptionally located at the northern end of Anna Maria Island, just ...
From $229 per night (USD)Expedia
- From $914 per night (USD)
VRBO
4 Bed \/ 4 Bath with Stunning Views of Bimini Bay !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You will love Bimini Bay Vue, its breathtaking, unobstructed 180-degree angle views of Bimini Bay are stunning. Complete ...
From $914 per night (USD)VRBO
- From $1225 per night (USD)
Expedia
New luxury home with rooftop views, balconies, and pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Sweet Caroline by AMI Locals Home in Anna Maria, FL 34216 VR23-000009 Welcome to Sweet Caroline, a newly constructed f ...
From $1225 per night (USD)Expedia
- From $798 per night (USD)
VRBO
Pier to Pier Paradise by Beach Boutique Rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning 4-bedroom home, aptly named Pier to Pier Paradise, offers breathtaking views of the Bay, luxury amenities, ...
From $798 per night (USD)VRBO
- From $791 per night (USD)
Expedia
Deja Blu:1 Block to Beach! Tropical Oasis, Poolside Lounge, Pool & Spa by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
208 Palm Ave, Anna Maria, FL 34217 What You'll Love About This Home: Location! 1 Block to the Beach! 3 Bedrooms / 3 Bat ...
From $791 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Meant to Be:1 Block to Beach! North End! Pool & Spa,Loaded Game Room by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
804 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1 Block to the Beach! AMI North End! ...
From $700 per night (USD)VRBO
- From $561 per night (USD)
Expedia
Mon Ami: Pine Ave Location! Pool! 3 Blocks to Gulf or Bay by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
311 Pine Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! On Pine Ave! 3 Blocks to Bay or Beach! 3 ...
From $561 per night (USD)Expedia
- From $891 per night (USD)
VRBO
Sea Creatures Cottage: Steps to beach! Putting Green, Rooftop Deck, Pool by Anna Maria Life
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
112 Mangrove Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! Steps to the Beach! No Streets to Cr ...
From $891 per night (USD)VRBO
- From $1008 per night (USD)
Expedia
Coastal home near the shopping district and Gulf beaches
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 8
Highlights: • 5 minute walk from the Gulf Beaches • Next to the Shopping District on Pine Ave. • Rooftop Deck • Ele ...
From $1008 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Shore's Nice - Renovated Pristine Modern Beach Cottage w\/ Peek-A-Boo Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Shore's Nice! On Anna Maria Island (Anna Maria, Florida) Renovated Pristine Modern Beach Cottage w/ Peek-A-B ...
From $371 per night (USD)VRBO
- From $520 per night (USD)
Expedia
Bay 2 Bay: Bay Across Street! Amazing Views of Bay & Canal, Pool & Lounge by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bay 2 Bay by Anna Maria Life Vacation Rentals 803 S. Bay Drive, Anna Maria, FL 34216 What You'll Love About This home: ...
From $520 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Anna Maria Island Direct Beachfront Condo- Awesome View and Amazing Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
View dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out ...
From $311 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Bean Point Beachfront- Beachfront 4 bedroom private home with pool\/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At A Glance Gulf-Front, Beach side Home Spacious Backyard Deck with Covered Dining Area, TV & Gas BBQ Grill NEW Private ...
From $600 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Sunset Point- Beachfront 4 bedroom with private pool with views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Point 765 North Shore Drive, Anna Maria What you will love about this property: • Direct Gulf Front • Beach is ...
From $500 per night (USD)VRBO
- From $1473 per night (USD)
Expedia
Spacious home with heated pool, jacuzzi, and rooftop deck
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
From Dusk 'Til Dune by AMI Locals Home in Anna Maria, FL 34216 Welcome to From Dusk 'Til Dune, a canal front home wit ...
From $1473 per night (USD)Expedia
- From $793 per night (USD)
VRBO
Beautiful Bean Point Home w\/ Gulf Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
NEW LISTING! Underwent complete INTERIOR REMODEL in Jan 2023!!! This Bean Point beauty is perfect for the family or grou ...
From $793 per night (USD)VRBO
- From $1048 per night (USD)
Expedia
The TipSea Turtle managed by Beach Retreats
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Views! Contactless entry Private heated pool & spa 3 hole mini-putt Parking for 4 Electric vehichle charger Fully Eq ...
From $1048 per night (USD)Expedia
- Click For Pricing
Expedia
3 Bedroom Townhome 319170 by Houzlet
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Great three bedroom /three bath Townhome with PRIVATE DOCK minutes to the beach, tucked away in one of the Island's best ...
Click For PricingExpedia
- From $386 per night (USD)
Expedia
Seahorse Cottage: Heated pool, north of Pine Ave, close to Bean Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Seahorse Cottage, your cozy 2-bedroom, 2-bathroom vacation rental on Anna Maria Island! Located north of Pine ...
From $386 per night (USD)Expedia