Anna Maria Rentals
From $591 per night (USD)VRBO
Wade N' Sea: On Canal, North End, 1 Block to Pine by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wade 'N Sea by Anna Maria Life Vacation Rentals 104 Gull Dr, Anna Maria, FL 34216 What You'll Love About This Home: Rec ...
From $591 per night (USD)VRBO
From $611 per night (USD)Expedia
Family-Friendly Canal Retreat with Pool and Steps to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coco Cottage by Anna Maria Island Accommodations 113 Los Cedros Dr., Anna Maria, Florida Welcome to Coco Cottage, yo ...
From $611 per night (USD)Expedia
From $1004 per night (USD)VRBO
Sea La Vie - Custom Home w/ Pool, Spa & Rooftop Deck on Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sea La Vie! On Anna Maria Island (Anna Maria, FL) A Luxurious Coastal Retreat on Anna Maria Island, Where St ...
From $1004 per night (USD)VRBO
From $1217 per night (USD)Expedia
Bimini Sunrise: On Canal! Dock! Pool! Rooftop Deck by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Sunrise is a new property and outstanding reviews are on the way! Bimini Sunrise by Anna Maria Life Vacation R ...
From $1217 per night (USD)Expedia
From $971 per night (USD)VRBO
Anna Maria Home with Pool and Rooftop Deck! 5-min Walk to Beach - Coconut Breeze
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Coconut Breeze Estate by Anna Maria Island Accommodations 703 N Bay Blvd, Anna Maria, Florida 34216 Escape to Coconut ...
From $971 per night (USD)VRBO
From $1097 per night (USD)Expedia
Rooftop Views! Pool, Spa and Game Room!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Love Me Blue by AMI Locals 792 Jacaranda Rd, Anna Maria, FL 34216 Welcome to Love Me Blue, a brand-new four bedroom, ...
From $1097 per night (USD)Expedia
From $1369 per night (USD)VRBO
Luxury Anna Maria Island Rental: Rooftop Deck, Pool, & Golf Cart at Deckadence
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Deckadance by AMI Locals Home in Anna Maria, FL 34216 Experience the ultimate getaway at Deckadance! This brand-new l ...
From $1369 per night (USD)VRBO
From $913 per night (USD)VRBO
Heavenly Hideaway, 3-bdrm house 5 min walk to the beach in beautiful Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Heavenly Hideaway, a Newly Renovated, exquisite canal-front vacation home featuring three bedrooms and three ...
From $913 per night (USD)VRBO
From $1286 per night (USD)VRBO
The Oasis at Palmetto - Coastal Retreat w/ Heated Pool, Spa, Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Oasis at Palmetto! On Anna Maria Island (Anna Maria, FL) Experience Unparalleled Island Living at The Oa ...
From $1286 per night (USD)VRBO
From $684 per night (USD)Expedia
Golf Cart - Beach Escape by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $684 per night (USD)Expedia
From $967 per night (USD)VRBO
Blue Mermaid Beach Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights - 2 minute walk to the Beach of Anna Maria Island - 5 minute walk to Pine Ave. • Private Pool • Outdoor Showe ...
From $967 per night (USD)VRBO
From $1838 per night (USD)Expedia
Coastal Elegance! Pool, Putting Green, Movie Room, and More!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Periwinkle Place by AMI Locals 226 Periwinkle Plaza, Anna Maria, FL 34216 Indulge in the ultimate luxury escape at Peri ...
From $1838 per night (USD)Expedia
From $998 per night (USD)VRBO
Salt Dreams: 1 Block to Beach! Pool, Spa, Games, Rooftop Deck by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Salt Dreams by Anna Maria Life Vacation Rentals 836 N Shore, Anna Maria, FL 34216 What You'll Love About This Home: Loc ...
From $998 per night (USD)VRBO
From $1134 per night (USD)Expedia
Luxury Beach House with Bay Views and Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Glass House by the Beach, a luxurious modern vacation retreat on Anna Maria Island, designed to immerse y ...
From $1134 per night (USD)Expedia
From $315 per night (USD)VRBO
The Twins: Your Perfect Budget Beach Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Photos Updated March 2025! Looking for a cozy, budget-friendly escape just steps from the beach? The Twins is the spot ...
From $315 per night (USD)VRBO
From $345 per night (USD)VRBO
Fish, Swim & Unwind: Anna Maria Apt Steps to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private Outdoor Shower | 11 Mi to Downtown Bradenton | 2 Blocks to Palmetto Ave Beach Indulge in the island getaway of ...
From $345 per night (USD)VRBO
From $319 per night (USD)VRBO
2 Blocks to Beach: Tropical Retreat in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Outdoor Shower | Perfect Place to Fish, Swim & Unwind | 11 Mi to Downtown Bradenton Indulge in the island getaway of yo ...
From $319 per night (USD)VRBO
From $847 per night (USD)Expedia
Book Magnolia Shores: Family-Friendly Getaway Near Beach with Pool & Mini Golf!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Magnolia Shores by Anna Maria Island Accommodations 304 Magnolia Ave. Anna Maria, FL 34216 Welcome to Magnolia Shores, ...
From $847 per night (USD)Expedia
From $635 per night (USD)VRBO
Paradise Pointe by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to your private waterfront oasis on Anna Maria Island at Paradise Pointe. *Features include* * Canal front wit ...
From $635 per night (USD)VRBO
From $1348 per night (USD)Expedia
Dolce Vita: Amazing Rooftop Experience, Views, Pool, Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Dolce Vita by Anna Maria Life Vacation Rentals 848 N Shore Drive, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1348 per night (USD)Expedia
From $287 per night (USD)VRBO
2b/1.5ba duplex unit short walk to gulf beach in quiet Anna Maria neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
216 Spring Avenue, is a 2b/1.5 duplex apartment located approximately 2 blocks to gulf beach where you can enjoy nice wa ...
From $287 per night (USD)VRBO
From $626 per night (USD)Expedia
Bayfront Beach access with Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views ...
From $626 per night (USD)Expedia
Click For PricingVRBO
Luxury Canalfront Home with Pool, 8 Min Walk to Beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Dancing with the Star by Anna Maria Island Accommodations Home in Anna Maria, Florida Welcome to Dancing with the St ...
Click For PricingVRBO
From $561 per night (USD)Expedia
Dock of the Bay by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Dock of the Bay! Located on the North end of Anna Maria, Dock of the Bay is a newly remodeled tw ...
From $561 per night (USD)Expedia
From $796 per night (USD)VRBO
Castle Azul: Luxury canal front w/pool, hot tub, putting green, and ping pong
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Photos updated April 2025! Welcome to Castle Azul, a stunning canal-front vacation home on Anna Maria Island! Just one ...
From $796 per night (USD)VRBO
From $841 per night (USD)VRBO
160 ft canal front, 2 boat lifts, cool- pool, cool mister-system, putting green
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a beautiful 4-bedroom house in Anna Maria for a wonderful getaway. Relax in a backyard paradise with moder ...
From $841 per night (USD)VRBO
From $668 per night (USD)VRBO
Holly Haven by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Holly Haven is your private waterfront oasis on Anna Maria Island. *Features include* * Canal front with private dock ...
From $668 per night (USD)VRBO
From $569 per night (USD)Expedia
Beautiful Home with Private Pool and Dock! Near Anna Maria Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis by Anna Maria Island Accommodations 5 Lakeview Place, Anna Maria, FL, 34216 Discover your perfect geta ...
From $569 per night (USD)Expedia
From $262 per night (USD)VRBO
Charming Cottage Near Bay and Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Twin Dolphins Cottage by Anna Maria Island Accommodations 520 Spring Ave Unit C, Anna Maria, Florida Welcome to Twin ...
From $262 per night (USD)VRBO
From $545 per night (USD)Expedia
Holly Hideaway: Spacious 2 bed, heated pool, screened lanai, 5-mins to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Holly Hideaway, your peaceful retreat nestled in a quiet neighborhood on the desirable North end of Anna Mari ...
From $545 per night (USD)Expedia
From $966 per night (USD)VRBO
Mintfish: Luxury canal-front w/heated pool, hot tub, docks, and water views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mintfish, your peaceful canal-front retreat tucked away on the north end of Anna Maria Island. This ground-le ...
From $966 per night (USD)VRBO
From $800 per night (USD)Expedia
AMI Swedish Beach House: Bay Front! Overlooking Tampa Bay! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AMI Swedish Beach House by Anna Maria Life Vacation Rentals 306 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About ...
From $800 per night (USD)Expedia
From $585 per night (USD)VRBO
Castaway Cove - Short stays! AMI gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax with friends and family at Castaway Cove, a true piece of paradise located at the north end of Anna Maria Island n ...
From $585 per night (USD)VRBO
From $467 per night (USD)Expedia
Coconut Tree: Canal-Front Home, Dock, Heated Pool & Covered Lanai
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Coconut Tree – your tropical retreat on Anna Maria Island, recently updated with all-new furnishings for your ...
From $467 per night (USD)Expedia
From $1177 per night (USD)VRBO
Compass Rose- 9 bedroom close to beach with rooftop
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 18
Compass Rose 9407 Gulf Drive, Anna Maria, FL 34216 What you will love about this property: • Luxury home with luxury fin ...
From $1177 per night (USD)VRBO
From $966 per night (USD)Expedia
From Dusk Til Dune- Canal front
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
From Dusk ‘Til Dune 404 North Shore Dr, Anna Maria, FL 34216 What you will love about this property: • Luxury home with ...
From $966 per night (USD)Expedia
From $753 per night (USD)VRBO
Anna Maria Beach House- 5 bedrooms close to beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Anna Maria Beach House 212 Spring Avenue, Anna Maria, FL 34216 What you will love about this property: • Luxury home wit ...
From $753 per night (USD)VRBO
From $1451 per night (USD)Expedia
Winding Waves- 9 bedrooms on canal
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 18
Winding Waves 9403 Gulf Dr, Anna Maria, FL 34216 What you will love about this property: • Luxury home with luxury fini ...
From $1451 per night (USD)Expedia
From $478 per night (USD)VRBO
Private Pool - Island Dream
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped k ...
From $478 per night (USD)VRBO
From $575 per night (USD)Expedia
Luxury Coastal Retreat with Pool and Rooftop Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
North End Escape by AMI Locals 800 Jacaranda Rd. Anna Maria, FL 34216 Welcome to North End Escape, a stylish three- ...
From $575 per night (USD)Expedia
From $1026 per night (USD)VRBO
Costa Bella: 4-Bedroom Home with Private Pool & Spa, Close to Beach & Pine Ave
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Costa Bella by Anna Maria Island Accommodations 10107 Gulf Dr Anna Maria, Florida 34216 Your family’s dream vacation aw ...
From $1026 per night (USD)VRBO
From $376 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 $376 per night (USD)VRBO
From $328 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 $328 per night (USD)VRBO
From $1072 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 $1072 per night (USD)Expedia
From $383 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 $383 per night (USD)VRBO
From $620 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 $620 per night (USD)Expedia
From $889 per night (USD)VRBO
Waterfront Elegance! Pool, Dock & Spa!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Curated Palm by Anna Maria Island Accommodations 520 Kumquat Drive, Anna Maria, Florida Welcome to The Curated P ...
From $889 per night (USD)VRBO
From $254 per night (USD)Expedia
Bayfront Escape Dock and Dog-Friendly Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
*As of May 2025, the dock is temporarily unavailable* Bay Cottage by AMI Locals 510 South Drive Unit B, Anna Maria, FL ...
From $254 per night (USD)Expedia
From $524 per night (USD)VRBO
Dock of the Bay: Waterfront Home! Perfect for Large Groups or Families in Anna M
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dock of the Bay by AMI Locals Waterfront Duplex in Anna Maria Welcome to Dock of the Bay, a stunning waterfront duple ...
From $524 per night (USD)VRBO
From $386 per night (USD)Expedia
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 $386 per night (USD)Expedia
From $1309 per night (USD)VRBO
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 $1309 per night (USD)VRBO
From $793 per night (USD)Expedia
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 $793 per night (USD)Expedia
From $550 per night (USD)VRBO
4 bedroom, pet friendly, Anna Maria Island beach home, sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The flAMIngo house is a 4 bedroom, 2 bath Key West style beauty with all the comforts of home! Let's flamingo to the bea ...
From $550 per night (USD)VRBO
From $428 per night (USD)Expedia
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 $428 per night (USD)Expedia
From $301 per night (USD)VRBO
Cozy Barefoot Bungalow: Steps to Bayfront Park & Bean Point, Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Barefoot Bungalow, a ground-level hideaway recently updated in early 2025. The open-concept living area welco ...
From $301 per night (USD)VRBO
From $1501 per night (USD)Expedia
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
2-minute walk to the beach 2 Kayaks you can launch from the back yard dock! • Private pool with in-ground spa • Watersli ...
From $1501 per night (USD)Expedia
From $1654 per night (USD)VRBO
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Welcome to Seaside Magnolia! From the moment you step through the front door, you are greeted by the subtle hues of the ...
From $1654 per night (USD)VRBO
From $582 per night (USD)Expedia
Paradise on Pine in Anna Maria
- 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-b ...
From $582 per night (USD)Expedia
From $1623 per night (USD)VRBO
Bleuphoria! Rooftop Views & Poolside Fun!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bleuphoria by AMI Locals 112 Elm Ave, Anna Maria, FL 34216 Welcome to Bleuphoria, a brand-new luxury four bedroom, f ...
From $1623 per night (USD)VRBO
Click For PricingExpedia
Wander Serendipity Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Beach is a coastal escape on Anna Maria Island, designed for both relaxation and recreation. It featu ...
Click For PricingExpedia
Click For PricingVRBO
Wander Serendipity Sea
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Sea is a peaceful coastal retreat on the North End of Anna Maria Island, with direct access to the Gu ...
Click For PricingVRBO
Click For PricingExpedia
Wander Serendipity Gulfront
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Gulfront is a breezy bohemian escape where the Gulf’s rhythm sets the tone. Start your day with ocean ...
Click For PricingExpedia
Click For PricingVRBO
Wander Serendipity Cloud
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Wander Serendipity Cloud is a luxurious retreat located within the Waterfront Greens Community at Deep Creek Lake, offer ...
Click For PricingVRBO
Click For PricingVRBO
Wander Serendipity Haven
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Haven is a luxury beachfront retreat on Anna Maria Island's North End, offering Gulf views, seamless ...
Click For PricingVRBO
From $442 per night (USD)VRBO
Welcome to Island Sea-Cret!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Sea-Cret by Anna Maria Vacations 4 Lakeview Place, Anna Maria, FL 34216 Welcome to Island Sea-Cret, a beautifu ...
From $442 per night (USD)VRBO
From $1038 per night (USD)Expedia
OASIS! 2min walk to Gulf,3 Kings/Twin Bunk,Salt Pool/Spa,Golf,6 Bikes,2 Hammocks
- 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 $1038 per night (USD)Expedia
From $907 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 $907 per night (USD)VRBO
From $672 per night (USD)Expedia
Bold Luxury Retro 3BR Oasis w/ Huge Heated Pool & Family Suite
- Bedrooms:
- 3
- 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 $672 per night (USD)Expedia
From $571 per night (USD)VRBO
Key Lime Cottage Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
🏝️ Key Lime Cottage – Beachfront Bliss on Anna Maria Island Welcome to Key Lime Cottage, your dreamy Gulf-front hideaw ...
From $571 per night (USD)VRBO
From $870 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 218 Palmetto Ave, Anna Maria, FL 34216 Welcome to A P ...
From $870 per night (USD)Expedia
Click For PricingVRBO
Wander Serendipity Sol
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Sol offers a luxurious beachfront escape just steps from the Gulf of Mexico, with direct beach access ...
Click For PricingVRBO
Click For PricingExpedia
Wander Serendipity Breeze
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Breeze is a stunning beachfront property in Anna Maria, Florida. Enjoy an expansive deck with sweepin ...
Click For PricingExpedia
Click For PricingVRBO
Wander Serendipity Waves
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Serendipity Beach is a renovated coastal retreat on Anna Maria Island, offering water views, direct beach access, ...
Click For PricingVRBO
From $644 per night (USD)Expedia
Nautical Sunrise- Canal front- 4 bedroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nautical Sunrise 510 Kumquat Drive , Anna Maria, FL 34216 What you will love about this property: • New pictures coming ...
From $644 per night (USD)Expedia
From $783 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 $783 per night (USD)VRBO
From $867 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 $867 per night (USD)Expedia
From $597 per night (USD)VRBO
New Rental! Special Intro Rates -Beautiful North End Home, Pool, close to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are excited to announce this beautiful new property to our rental program. Be one of the first to rent and review!! ...
From $597 per night (USD)VRBO
From $841 per night (USD)Expedia
Waterfront Anna Maria Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Anna Maria Oasis, your perfect escape on beautiful Anna Maria Island! *Military discounts available You’ve ...
From $841 per night (USD)Expedia
From $488 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. Enjoy easy Is ...
From $488 per night (USD)VRBO
From $702 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 $702 per night (USD)Expedia
From $689 per night (USD)VRBO
Click for Discount! Beach House w/ pool on the north end of AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hammock Hideaway! ⚓.02 Miles to Pine Ave. Shopping, Restaurants, and more! ⚓.03 Miles to AMI Beaches ⚓Priv ...
From $689 per night (USD)VRBO
From $1090 per night (USD)Expedia
CHRISTMAS available! New Breathtaking Canal front Home on Best street in AMI!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to your dream getaway on Anna Maria Island! This stunning brand new beach house offers the perfect blend of luxu ...
From $1090 per night (USD)Expedia
From $946 per night (USD)VRBO
Acacia Breeze by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to Acacia Breeze for an unforgettable Anna Maria Island getaway! There are so many areas to explore at this ...
From $946 per night (USD)VRBO
From $495 per night (USD)Expedia
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 fami ...
From $495 per night (USD)Expedia
From $589 per night (USD)VRBO
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 ...
From $589 per night (USD)VRBO
From $822 per night (USD)Expedia
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to SunSalt Cottage! This AMI Oasis is perfectly located in the heart of Anna Maria Island! •Large Private Saltw ...
From $822 per night (USD)Expedia
From $310 per night (USD)VRBO
Tiny Tides: Adorable Cozy House!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Tiny Tides by Anna Maria Island Accommodations 520 Spring Ave Unit A, Anna Maria, FL 34216 Welcome to Tiny Tides, a coz ...
From $310 per night (USD)VRBO
From $979 per night (USD)Expedia
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to your dream vacation home in Anna Maria! This stunning 6-bedroom, 6.5-bath luxury retreat is perfectly situate ...
From $979 per night (USD)Expedia
From $1038 per night (USD)VRBO
NEW! Blue Crush! Steps to the Beach! Only 5 Homes Away! Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your coastal retreat at Blue Crush! On the ground floor, you’ll find a private living room with a big-screen ...
From $1038 per night (USD)VRBO
From $490 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. Ind ...
From $490 per night (USD)Expedia
From $1090 per night (USD)VRBO
AMI Oasis! Pine Avenue is Next Door!~Heated pool/Putt Putt~Steps to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Discover this 4-bedroom gem in Anna Maria. This amazing house features 4 king beds, perfect for a comfortable stay. With ...
From $1090 per night (USD)VRBO
From $1264 per night (USD)Expedia
NEW! Blue Pearl~Heated Pool/Spa~Walkable Pine Ave! Guest House for Added Space!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Pearl – 411 Spring Ave, Anna Maria Relax with the whole family at this peaceful place to stay. Welcome to Blue Pea ...
From $1264 per night (USD)Expedia
From $1255 per night (USD)VRBO
519 Loquat Drive Summ
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to your vacation rental a stunning home nestled in the heart of Anna Maria Island where the serene in ...
From $1255 per night (USD)VRBO
From $2006 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 $2006 per night (USD)Expedia
From $730 per night (USD)VRBO
Mermaid’s Purse - Private Pool! 40 steps to beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• 2-minute walk to the beach • Private Heated Pool • Washer and dryer • Dog friendly • Less than a 5-minute walk from Pi ...
From $730 per night (USD)VRBO
From $1626 per night (USD)Expedia
Gorgeous canal front home on Anna Maria!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
"Shell We Dance" is a charming coastal retreat located on Anna Maria Island, perfect for those seeking a relaxing getawa ...
From $1626 per night (USD)Expedia
From $1120 per night (USD)VRBO
NEW! Meet Me At Sunset! 3 Homes from the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Meet Me at Sunset! This 4BR, 4.5BA beach-boho villa offers private balconies and a heated pool with spa. Just ...
From $1120 per night (USD)VRBO
From $862 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 $862 per night (USD)Expedia
From $1014 per night (USD)VRBO
Hammock Daze-4bedroom/3.5bath-Pool/Canal HOME. 10P
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This stunning 4Bedroom/3.5Bath Luxury Canal Home is an absolutely ideal choice for a family holiday to AMI! Conveniently ...
From $1014 per night (USD)VRBO
From $473 per night (USD)Expedia
Cozy Cottage - POOL HOME! 3/3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A Cozy Cottage is the ultimate retreat for relaxation and reconnecting with family and friends. Each bedroom offers dire ...
From $473 per night (USD)Expedia