Anna Maria Rentals
From $392 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #9 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $392 per night (USD)VRBO
From $268 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden # 17 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $268 per night (USD)Expedia
From $335 per night (USD)VRBO
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Breeze, our newly renovated home with 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natu ...
From $335 per night (USD)VRBO
From $242 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #15 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $242 per night (USD)Expedia
From $380 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $380 per night (USD)VRBO
From $273 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $273 per night (USD)Expedia
From $358 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Garden #11 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $358 per night (USD)VRBO
From $375 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sunrise Garden #2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $375 per night (USD)Expedia
From $238 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #16 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $238 per night (USD)VRBO
From $385 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $385 per night (USD)Expedia
From $270 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $270 per night (USD)VRBO
From $315 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Garden #8 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $315 per night (USD)Expedia
From $558 per night (USD)VRBO
Crescent Palms north end AMI, 2 King suites,walk to bay beach stunning pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Create unforgettable memories at Crescent Palms. This *perfect island house* has been fully renovated after hurricanes ...
From $558 per night (USD)VRBO
From $796 per night (USD)Expedia
Pineapple Cottage, walk to the beach &Pine Ave, tropical oasis pool and spa.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Pineapple Cottage a beautifully updated ground-level beach cottage located in the heart of Anna Maria City a ...
From $796 per night (USD)Expedia
From $590 per night (USD)VRBO
Island in the Sun, luxury beach house with private pool, walk to Pine Ave
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME to Island in the Sun this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurrica ...
From $590 per night (USD)VRBO
From $236 per night (USD)Expedia
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $236 per night (USD)Expedia
From $268 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $268 per night (USD)VRBO
From $545 per night (USD)Expedia
Coconut Lagoon – Pet Friendly Home w/ Heated Pool, Screened Porch & Cabana TV
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p>A short distance from sailing, scuba diving, and more, this family-friendly vacation home lets you experience it all. ...
From $545 per night (USD)Expedia
From $264 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $264 per night (USD)VRBO
From $270 per night (USD)Expedia
Shell Cottage - sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shell Cottage is situated towards the top end of Anna Maria Island. It is one of a cluster of the 3 cottages sharing th ...
From $270 per night (USD)Expedia
From $784 per night (USD)VRBO
On the BEACH block! Luxury home, Pool and Spa, stay and relax with your friends!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Villa La Concha by Anna Maria Island Accommodations Home in Anna Maria, FL Welcome to Villa La Concha, a marvelous ...
From $784 per night (USD)VRBO
From $2120 per night (USD)Expedia
Luxury beachfront home with private pool, putting green, golf cart and bikes!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Bay View Beauty by AMI Locals Home in Anna Maria, FL Highlights • Waterfront luxury home •Located on our beautiful Bay ...
From $2120 per night (USD)Expedia
From $628 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Photo Updated March 2025! Treat yourself to the beachside vacation you’ve been dreaming of with this relaxing and dog-f ...
From $628 per night (USD)VRBO
From $521 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Situated on the north end of Anna Maria Island, The Sandy Rose is the perfect location for your next getaway! This 4 bed ...
From $521 per night (USD)Expedia
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Luxury Home Close to Beach! Pool, Putting Green, and Outdoor Games!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Seaside Magnolia by Anna Maria Island Accommodations Holmes Beach Luxury Vacation Home Near Beaches VRC18-000096 Step ...
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From $284 per night (USD)Expedia
Seahorse Cottage - sleeps 2 guests in 1 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property is situated towards the top end of Anna Maria Island. It is one of a cluster of 3 cottages which have the ...
From $284 per night (USD)Expedia
From $903 per night (USD)VRBO
Stunning luxury home just 1 block to beach! Pool, spa, and elevator!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Palmetto Pointe by AMI Locals Home in Anna Maria, FL Highlights: - Private wrap around balconies - Rooftop deck - Foos ...
From $903 per night (USD)VRBO
From $559 per night (USD)Expedia
La Buena Vida – Luxury 3BR Canal Home w/ Pool, Spa & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to La Buena Vida! On Anna Maria Island (Anna Maria, FL) La Buena Vida is a luxurious 3-bedroom waterfront home ...
From $559 per night (USD)Expedia
From $265 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #10 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $265 per night (USD)VRBO
From $628 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to waterfront paradise at Bellablu! This newly renovated haven offers the ideal retreat for your next vacation. W ...
From $628 per night (USD)Expedia
From $863 per night (USD)VRBO
Charming Beachfront Bungalow with Sunset Views and Coastal Comfort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
High Tide by AMI Locals Charming Beachfront Bungalow with Sunset Views and Coastal Comfort 108 Elm Ave, Unit B Anna ...
From $863 per night (USD)VRBO
From $898 per night (USD)Expedia
Experience Bay Happy: Retreat with Pool Steps from the Beach Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Happy by AMI Locals Anna Maria, Florida VR21-000047 Bay Happy is a fun-filled haven! It features a spacious backy ...
From $898 per night (USD)Expedia
Click For PricingVRBO
Luxury Home with Private Covered Pool and Putting Green - AMI Oasis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
AMI Oasis by AMI Locals Home in Anna Maria, FL Welcome to AMI Oasis! This luxurious four-bedroom and four-bathroom retr ...
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From $618 per night (USD)Expedia
Dog Friendly Cottage - Near the Beach and Shopping!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Aquaville B by AMI Locals Home in Anna Maria VR18-000018 Welcome to Aquaville B, a three-bedroom and one bath beach-s ...
From $618 per night (USD)Expedia
From $836 per night (USD)VRBO
On the beach block! Beautiful Home with Rooftop Deck, Pool and Spa!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Montego Bay by AMI Locals Home in Anna Maria, Florida VR16-000472 Welcome to Montego Bay, a spectacular home with a pri ...
From $836 per night (USD)VRBO
Click For PricingExpedia
Batley's Beach House: Perfect location, ground-level rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Photos Updated April 2025 Located in the "heart" of Anna Maria City, sits this ground level, 3 bedroom, 2 bath home jus ...
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From $1620 per night (USD)VRBO
Canal Front Home with Dock! Putting Green, Pool with Waterslide
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Tortuga Bay by Anna Maria Island Locals Home in Anna Maria, FL Welcome to the newly remodeled Tortuga Bay! This five-be ...
From $1620 per night (USD)VRBO
From $503 per night (USD)Expedia
Adorable Beach cottage just steps Bean Point beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bean Point Bungalow by Anna Maria Island Locals Home in Anna Maria, FL Highlights • 5-minute walk from the Beach • Pri ...
From $503 per night (USD)Expedia
From $567 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
***Photos Updated May 2025*** Come slip away to this luxurious island retreat where all of your cares will drift away! T ...
From $567 per night (USD)VRBO
From $731 per night (USD)Expedia
Dog friendly home near the Gulf!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Coast is Clear by AMI Locals Home in Anna Maria, Florida VR22-000035 Welcome to Coast is Clear, a refreshing beach home ...
From $731 per night (USD)Expedia
From $2595 per night (USD)VRBO
Beachfront - New Listing!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
The Diamond Star Beach House ***Brand New 2025 Remodel*** Welcome to The Diamond Star! Experience beachfront living ...
From $2595 per night (USD)VRBO
From $398 per night (USD)Expedia
Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BRAND NEW POOL! Located on the coveted northern end of Anna Maria Island, “Maria's Way” is a charming beach cottage off ...
From $398 per night (USD)Expedia
From $948 per night (USD)VRBO
One block off Pine Ave w/ Amazing Rooftop Views! - AMI Memories
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
AMI Memories by AMI Locals Home in Anna Maria VR20-000052 Welcome to AMI Memories! This three-level home boasts fiv ...
From $948 per night (USD)VRBO
From $775 per night (USD)Expedia
Luxury home with AMAZING backyard Pool and Spa! So close to beach and shopping!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Daiquiri Deck by AMI Locals Home in Anna Maria, Florida VR18-000093 Welcome to Daiquiri Deck, a stunning four-bedroom a ...
From $775 per night (USD)Expedia
From $687 per night (USD)VRBO
Blue Bayou | Family fun pool home with hot tub, canalfront with a dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
From $687 per night (USD)VRBO
From $741 per night (USD)Expedia
Luxury 5* home & private pool on AMI, one of the prettiest towns on gulf coast!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom o ...
From $741 per night (USD)Expedia
From $324 per night (USD)VRBO
Charming cottage in quiet area, close to beach & bay.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in t ...
From $324 per night (USD)VRBO
From $583 per night (USD)Expedia
Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool h ...
From $583 per night (USD)Expedia
From $351 per night (USD)VRBO
Dreamscape: North End Pool Home, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dreamscape by Anna Maria Life Vacation Rentals 773 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $351 per night (USD)VRBO
From $318 per night (USD)Expedia
Beach N Bay 204 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 204! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your ch ...
From $318 per night (USD)Expedia
From $833 per night (USD)VRBO
Home just steps to BEACH! Private pool and spa - Sign of the Mermaid
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Sign of the Mermaid by AMI Locals Home in Anna Maria, Florida VR17-000054 Welcome to Sign of the Mermaid, a luxurious ...
From $833 per night (USD)VRBO
From $1006 per night (USD)Expedia
The Perfect Gulf Front Vacation, Directly on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Osprey House, Gulf front vacation rental-located on the North end of Anna Maria Island. Located directly on t ...
From $1006 per night (USD)Expedia
From $516 per night (USD)VRBO
The Palm Leaf by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Palm Leaf is a newly remodeled three-bedroom, two-bathroom private home with a pool and spa. This fabulous house is ...
From $516 per night (USD)VRBO
From $490 per night (USD)Expedia
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location.... recently remodeled and improved after storms... surrounded by multi million dollar home ...
From $490 per night (USD)Expedia
From $590 per night (USD)VRBO
The Salted Coconut by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Salted Coconut is just a short stroll to the beautiful beaches of Anna Maria! This gorgeous home is a 3-bedroom, 3-b ...
From $590 per night (USD)VRBO
From $358 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***Photos Updated June 2025*** This newly renovated 2-bedroom, 2-bathroom cottage truly lives up to its name. Completed ...
From $358 per night (USD)Expedia
From $546 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You'll fall in love with Mermaid Cove the second you step inside. This beautifully refurbished property boasts all the m ...
From $546 per night (USD)VRBO
From $1169 per night (USD)Expedia
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Photos updated March 2025! Newly redesigned in 2025, this stunning 4-bedroom, 3.5-bathroom beach house offers the perfe ...
From $1169 per night (USD)Expedia
From $640 per night (USD)VRBO
Canal front pool home on the north end of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
What more could you want from a vacation rental then a beautiful Mediterranean inspired canal home nestled into the priv ...
From $640 per night (USD)VRBO
From $910 per night (USD)Expedia
Ocean Walk- 5 bedroom heated pool/spa and 6 houses from the white sandy beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
At A Glance North-facing private heated pool with a spa Steps to the beach Loft and bonus rec room by the pool Part of o ...
From $910 per night (USD)Expedia
From $568 per night (USD)VRBO
Private Tropical Oasis - Tarpon Point - Pool/Spa, Perfect Island Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this charming 3 bedroom, 2 bathroom island oasis nestled into a corner lot within walking distance to The Gulf ...
From $568 per night (USD)VRBO
From $528 per night (USD)Expedia
A Wave From It All - Oasis w/ Pool, Cabana, Putting Green & Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
<p>A short distance from sailing, scuba diving, and more, this pet-friendly vacation home lets you experience it all. Th ...
From $528 per night (USD)Expedia
From $740 per night (USD)VRBO
Yellowbird: AMI North End, Gulf Views, Pool, Tiki Hut, Elevator by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Yellowbird by Anna Maria Life Vacation Rentals 705 North Shore Dr., Anna Maria, FL 34216 What You'll Love About This Ho ...
From $740 per night (USD)VRBO
From $342 per night (USD)Expedia
Bay Breeze Cottages #1 (The Mahi-Mahi)
- 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 $342 per night (USD)Expedia
From $572 per night (USD)VRBO
Beautiful Luxury Southern Style Home located in Anna Maria - Walk easily to Beach, Sleeps 6!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Southern Belle Beach House located just steps away from the Gulf beaches of Anna Maria Island. Southern Belle ...
From $572 per night (USD)VRBO
From $385 per night (USD)Expedia
CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**ASK ABOUT LAST-MINUTE DEALS! All of the comforts of home in this tastefully designed 4-bedroom 3-bath gro ...
From $385 per night (USD)Expedia
From $405 per night (USD)VRBO
HEATED POOL & SPA ON CANAL, FREE WiFi & Trolley, Close to Beach & Bay!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
**ASK ABOUT LAST MINUTE DEALS! Families or groups of friends love this big open house with plenty of room a ...
From $405 per night (USD)VRBO
From $708 per night (USD)Expedia
New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedrooms, 3 Bathrooms home plus loft th ...
From $708 per night (USD)Expedia
From $729 per night (USD)VRBO
Magnolia walk to beach/shops, AMI perfect Location, private lagoon pool/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover island paradise at Magnolia located on Magnolia Ave. , a *premier residential street* just south of Pine Ave. i ...
From $729 per night (USD)VRBO
From $366 per night (USD)Expedia
Heated Pool & Spa, FREE WiFi, Near AMI Beach & Village, Dog* (See Note)...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly updated to become your favorite place to stay on the Island, Lakeview Cottage boasts a private heated pool and spa ...
From $366 per night (USD)Expedia
From $691 per night (USD)VRBO
Glory Days: AMI North End, Backyard Oasis, Pool, 1.5 Bocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Glory Days by Anna Maria Life Vacation Rentals 206 Archer Way, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $691 per night (USD)VRBO
From $414 per night (USD)Expedia
Escape to Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Ave Maria! We are a 5 minute walk to Anna Maria Beach. Head on down to Bean Point, located on the norther ...
From $414 per night (USD)Expedia
From $764 per night (USD)VRBO
Do you love the beach?
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Seaside Sanctuary is the ground level unit of a beachfront duplex. It is the 2nd home from the beach with no roads ...
From $764 per night (USD)VRBO
From $761 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Aloha Beaches a newly renovated custom beach destination. Kick off your shoes, turn off your phone, don’t win ...
From $761 per night (USD)Expedia
From $1207 per night (USD)VRBO
Dolphin Tales: Pool, Bay Views & Private Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dolphin Tales by Anna Maria Life Vacation Rentals 836 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1207 per night (USD)VRBO
From $438 per night (USD)Expedia
The Lady Fish by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on the far North end of Anna Maria Island, with the beach cottage is just around the corner, The Lady Fish is a ...
From $438 per night (USD)Expedia
From $831 per night (USD)VRBO
Golf Cart - Coconut Cove by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be o ...
From $831 per night (USD)VRBO
From $2033 per night (USD)Expedia
Cloud 9- beachfront/heated pool/ 4 plus bedroom
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den Located on the North End of Anna Maria Island. Professionally decora ...
From $2033 per night (USD)Expedia
From $1217 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Big Family Beach House, the name says it all! Coastal elegance describes this spectacular large family home. It's loca ...
From $1217 per night (USD)VRBO
From $1976 per night (USD)Expedia
luxury beachfront/ heated pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 4.5 bath Beach Front Home with a Beach Front Heated Pool and Spa,Gourmet Kitchen, high end finishes and one o ...
From $1976 per night (USD)Expedia
From $510 per night (USD)VRBO
Charming Canal front Luxury home with brand-new Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Dockside Paradise! Dockside Paradise is a perfect canal front retreat centrally located in Anna Maria! Comp ...
From $510 per night (USD)VRBO
From $1045 per night (USD)Expedia
Amie House Mod BEACH Getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Amie House on Anna Maria Island. Modern Amie House is perfectly situated a short 4 minute walk to the pri ...
From $1045 per night (USD)Expedia
From $861 per night (USD)VRBO
Oceans Blue Walk to the beach,stunning pool/spa private dock great location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in the ultimate beach escape to Oceans Blue located on the *premier corner* of Coconut & Los Cedros in Anna Mari ...
From $861 per night (USD)VRBO
From $538 per night (USD)Expedia
Sol Mate – Updated 3BR Home w/ Heated Pool, Spa, Walk to Bean Point Beach & Pine Ave, Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sol Mate! On Anna Maria Island (Anna Maria, FL) Bright and Beautifully Updated 3-Bedroom Home with Heated Po ...
From $538 per night (USD)Expedia
From $564 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
You want WARMTH –You want SUN – You NEED BEACH – KINGFISH is just the thing! Escape to one of Anna Maria Island’s most ...
From $564 per night (USD)VRBO
From $514 per night (USD)Expedia
A Ray Of Sunshine- Amazing property private basketball court pool/spa on a canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Ray of Sunshine 232 Chilson Avenue Anna Maria Island, FL 34216 AT A GLANCE Newly remodeled professionally decorated ...
From $514 per night (USD)Expedia
From $880 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Anapauo Beachhouse! Pronounced ahn-ap-ow’-o, it is a Greek word meaning to give rest, refresh, recover and co ...
From $880 per night (USD)VRBO
From $472 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to "A Time Out" - your perfect retreat in paradise! This charming 4-bedroom, 2-bathroom home invites you to expe ...
From $472 per night (USD)Expedia
From $525 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you're looking to escape the hustle and bustle of everyday life, look no further than "Lovin' the SANND". This three ...
From $525 per night (USD)VRBO
From $494 per night (USD)Expedia
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Di ...
From $494 per night (USD)Expedia
From $505 per night (USD)VRBO
Havana Cay- Adorable cottage- only 4 houses from beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
At a Glance Historic 1924 Latin style home with deluxe renovations Only 4 houses in from the beach- a 30 second walk to ...
From $505 per night (USD)VRBO
From $668 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Live out your dream of a tropical paradise at our Key West style beach house on the North end of Anna Maria. Start your ...
From $668 per night (USD)Expedia
From $1170 per night (USD)VRBO
Stunning new luxury home, pool + spa, walk to the beach! Summer awaits!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Oar House by AMI Locals Home in Anna Maria, FL Located in the most desired North End of Anna Maria Highlights: - Ne ...
From $1170 per night (USD)VRBO
From $1441 per night (USD)Expedia
Gorgeous Canal Front Luxury home, Pool, Spa, Dock, and Rooftop Deck - Sail Away
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Sail Away by AMI Locals Home in Anna Maria, FL VR19-000048 Welcome to Sail Away—an exquisite six-bedroom, six-and-a-h ...
From $1441 per night (USD)Expedia
From $408 per night (USD)VRBO
Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Welcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home h ...
From $408 per night (USD)VRBO
From $520 per night (USD)Expedia
Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Southern Magnolia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $520 per night (USD)Expedia
From $1387 per night (USD)VRBO
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
HGTV Beach Hunters Renovated Beach Front Home with a heated pool and 3 bedrooms. 1 Paddle boards & 2 kayak included. ...
From $1387 per night (USD)VRBO
From $646 per night (USD)Expedia
September Golf Cart Special
- 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 $646 per night (USD)Expedia
From $476 per night (USD)VRBO
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) After sustaining hurricane damage, this charming ...
From $476 per night (USD)VRBO
From $291 per night (USD)Expedia
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Flexible Check-in and checkout days —with some exceptions for holidays and certain times of the year—and never on Sunday ...
From $291 per night (USD)Expedia