Anna Maria, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anna Maria, Florida on RentalSaver.com!

Anna Maria Rentals

From $1150 per night (USD)
VRBO
New Luxury Getaway on Anna Maria Island
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to your vacation rental, a stunning home nestled in the heart of Anna Maria Island, where the serene intercoasta ...
From $1150 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Bean Point Bliss by Duncan Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bean Point Bliss! This stunning 3-bedroom, 2-bathroom pool home has plenty of room for the whole family. Bean ...
From $482 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Rainbow Fish: 1.5 blocks to beach! Pool, Spa & Game Room
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Rainbow Fish by Anna Maria Life Vacation Rentals 210 Archer Way, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $635 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Family Getaway at A Change in Latitude: Private Pool, Games, 5 Mins to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A Change in Latitude by AMI Locals Home in Anna Maria, Florida Welcome to A Change in Latitude! This elevated three-bed ...
From $493 per night (USD)
Expedia
From $942 per night (USD)
VRBO
Coral Reef: 50ft to Beach, Games Galore, Rooftop Deck, Pool, Spa by Anna Maria Life Vacation Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Coral Reef by Anna Maria Life Vacation Rentals 118 Mangrove Ave, Anna Maria, FL 34216 What You'll Love About this House ...
From $942 per night (USD)
VRBO
From $763 per night (USD)
Expedia
AMI Du Soleil | Steps to the Beach, Heated Pool, Anna Maria Island, IMG
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to 'AMI Du Soleil' a ‘friend of the sun’ by StayDream Vacations. ✨"Great hosts, great house, great location. ...
From $763 per night (USD)
Expedia
From $1755 per night (USD)
VRBO
Villa la Esperanza Jacaranda
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious Beach Getaway – Private Pool, Jacuzzi & Kayaks Included! Escape to paradise with this spacious, upscale beach ...
From $1755 per night (USD)
VRBO
$Serenity Cottage\n$
From $1007 per night (USD)
Expedia
Serenity Cottage\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Featuring air-conditioned accommodation with a private pool, sea view and a balcony, Serenity Cottage is located in Anna ...
From $1007 per night (USD)
Expedia
From $928 per night (USD)
VRBO
September Golf Cart Special
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Dockside Dream is a luxurious canal-front retreat on beautiful Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom ...
From $928 per night (USD)
VRBO
From $654 per night (USD)
Expedia
The 19th Hole | Luxury AMI Beach Home - Private Pool & Spa, 7 Hole Putting Green!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to The 19th Hole: Your Perfect Anna Maria Island Vacation Rental Experience the best of Anna Maria Island at The ...
From $654 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
Pool/Spa - Bean Point Retreat by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
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 $1072 per night (USD)
VRBO
From $2085 per night (USD)
VRBO
Luxury 3-Story Beach Home with Pool & Spa, Anna Maria
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Escape to paradise in this stunning 5-bedroom, 4-bathroom luxury home on Anna Maria Island, designed with modern beach a ...
From $2085 per night (USD)
VRBO
From $481 per night (USD)
VRBO
September Golf Cart Special
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Photos Updated November 2024! Magnolia Cottage is your perfect escape to Anna Maria Island, combining the charm of coast ...
From $481 per night (USD)
VRBO
From $933 per night (USD)
Expedia
Luna Sea | Anna Maria Beach Home Rental - Steps from the Sea!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Luna Sea – Your Private Slice of Paradise on Anna Maria Island! Escape to a serene coastal haven just 100 ste ...
From $933 per night (USD)
Expedia
From $740 per night (USD)
VRBO
Anna Maria Island of Palms - HotTub,Pool,Poker,Games and more
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to ISLAND OF PALMS – Your Ultimate Vacation Retreat! Escape to this stunning 5-bedroom, 3-bathroom coastal home ...
From $740 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Boho Island Home, Pool and 1 Min to Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Bohemian Breeze by AMI Locals Anna Maria Vacation Home 429 Hibiscus Road, Anna Maria, FL 34217 Welcome to Bohemian B ...
From $545 per night (USD)
Expedia
From $1112 per night (USD)
VRBO
Bikini's & Martini's Waterfront Canal: 1 Block to Beach! Dock! On Canal! Anna Maria Life
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bikini's & Martini's Waterfront Canal by Anna Maria Life Vacation Rentals 215 Chilson Ave, Anna Maria, FL 34216 Locatio ...
From $1112 per night (USD)
VRBO
From $552 per night (USD)
Expedia
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 $552 per night (USD)
Expedia
From $1099 per night (USD)
VRBO
Family-Friendly Canal Retreat with Pool and Steps to the Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Coco Cottage by Anna Maria Island Accommodations Family-Friendly Canal Retreat with Pool and Steps to the Beach 113 L ...
From $1099 per night (USD)
VRBO
From $858 per night (USD)
Expedia
Sea La Vie - Custom 3BR 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) Highlights - Expansive Living Space. - Bedrooms: 1 King Pr ...
From $858 per night (USD)
Expedia
From $1214 per night (USD)
VRBO
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 $1214 per night (USD)
VRBO
From $770 per night (USD)
Expedia
Stay at Anna Maria Home 3-Min Walk to the Beach with Pool and Rooftop Deck!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Coconut Breeze Estate by Anna Maria Island Accommodations Luxury Beachfront Home with Pool and Rooftop Deck VRC20-000M ...
From $770 per night (USD)
Expedia
From $1835 per night (USD)
VRBO
Exclusive Luxury Pool Home on Anna Maria Island, Steps to Bean Point Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Love Me Blue by AMI Locals 792 Jacaranda Rd. Anna Maria, FL 34216 Experience your vacation dreams at Love Me Blue! Th ...
From $1835 per night (USD)
VRBO
From $1088 per night (USD)
Expedia
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 $1088 per night (USD)
Expedia
From $906 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 $906 per night (USD)
VRBO
From $965 per night (USD)
Expedia
The Oasis at Palmetto - Coastal Chic Retreat w/ Heated Pool, Spa & Balconies Steps to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to The Oasis at Palmetto! On Anna Maria Island (Anna Maria, FL) Highlights - Bedrooms Master Suite: King bed wi ...
From $965 per night (USD)
Expedia
From $630 per night (USD)
VRBO
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 $630 per night (USD)
VRBO
From $590 per night (USD)
Expedia
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 $590 per night (USD)
Expedia
From $1320 per night (USD)
VRBO
Coastal Chic Retreat with Pool Near Gulf Beaches
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
Periwinkle Place by AMI Locals 226 Periwinkle Plaza, Anna Maria, FL 34216 Welcome to Periwinkle Place, a stunning con ...
From $1320 per night (USD)
VRBO
From $841 per night (USD)
Expedia
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 $841 per night (USD)
Expedia
From $861 per night (USD)
VRBO
September Golf Cart Special
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 $861 per night (USD)
VRBO
From $298 per night (USD)
Expedia
September Golf Cart Special
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 $298 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Fish, Swim & Unwind: Anna Maria Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private Outdoor Shower | 11 Mi to Downtown Bradenton | Walk to Palmetto Ave Beach Indulge in the island getaway of your ...
From $322 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Walk to Beach: Tropical Retreat in Anna Maria
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Outdoor Shower | 11 Mi to Downtown Bradenton Indulge in the island getaway of your dreams when you stay at this 2-bed, ...
From $336 per night (USD)
Expedia
From $426 per night (USD)
VRBO
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 $426 per night (USD)
VRBO
From $609 per night (USD)
Expedia
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 $609 per night (USD)
Expedia
From $1115 per night (USD)
VRBO
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 $1115 per night (USD)
VRBO
From $292 per night (USD)
VRBO
2b/1ba duplex unit brisk walk to gulf beach in quiet Anna Maria neighborhood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
218 Spring Avenue, is a charming 2b/1ba duplex apartment approximately 2 blocks walking distance to gulf beach where you ...
From $292 per night (USD)
VRBO
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 $652 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 $652 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $542 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 $542 per night (USD)
Expedia
Click For Pricing
VRBO
Birdsong: Anna Maria Island Retreat with Pool, Steps to Beach & Pet-Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Birdsong by Anna Maria Island Accommodations 709 Fern St, Anna Maria, Florida 34216 Welcome to Birdsong, a picture-pe ...
Click For Pricing
VRBO
From $675 per night (USD)
Expedia
September Golf Cart Special
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 $675 per night (USD)
Expedia
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)
Expedia
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)
Expedia
From $677 per night (USD)
VRBO
Beautiful Home with Private Pool and Dock! Near Anna Maria Beaches!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Oasis by Anna Maria Island Accommodations Holmes Beach Bayfront Home with Pool & Dock Discover your perfect get ...
From $677 per night (USD)
VRBO
From $454 per night (USD)
Expedia
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 $454 per night (USD)
Expedia
From $485 per night (USD)
VRBO
September Golf Cart Special
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 $485 per night (USD)
VRBO
From $829 per night (USD)
Expedia
September Golf Cart Special
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 $829 per night (USD)
Expedia
From $919 per night (USD)
VRBO
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 $919 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Castaway Cove - Short stays! AMI gem!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with friends and family at Castaway Cove, a true piece of paradise located at the north end of Anna Maria Island n ...
From $864 per night (USD)
Expedia
From $441 per night (USD)
VRBO
September Golf Cart Special
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 $441 per night (USD)
VRBO
From $1121 per night (USD)
Expedia
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 $1121 per night (USD)
Expedia
From $796 per night (USD)
VRBO
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 $796 per night (USD)
VRBO
From $712 per night (USD)
Expedia
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 $712 per night (USD)
Expedia
From $1251 per night (USD)
VRBO
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 $1251 per night (USD)
VRBO
From $428 per night (USD)
Expedia
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 $428 per night (USD)
Expedia
From $1080 per night (USD)
VRBO
Luxury Coastal Retreat with Pool, Rooftop Deck and Prime
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
North End Escape by AMI Locals Luxury Coastal Retreat with Pool, Rooftop Deck and Prime North-End Location 800 Jacara ...
From $1080 per night (USD)
VRBO
From $880 per night (USD)
Expedia
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 $880 per night (USD)
Expedia
From $373 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 $373 per night (USD)
VRBO
From $402 per night (USD)
Expedia
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 $402 per night (USD)
Expedia
From $921 per night (USD)
VRBO
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 $921 per night (USD)
VRBO
From $375 per night (USD)
Expedia
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 $375 per night (USD)
Expedia
From $784 per night (USD)
VRBO
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 $784 per night (USD)
VRBO
From $854 per night (USD)
Expedia
The Curated Palm: Book now to secure your summer spot!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Curated Palm by Anna Maria Island Accommodations 520 Kumquat Drive, Anna Maria, FL Discover The Curated Palm, a stu ...
From $854 per night (USD)
Expedia
From $468 per night (USD)
VRBO
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 $468 per night (USD)
VRBO
From $469 per night (USD)
Expedia
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 $469 per night (USD)
Expedia
From $316 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 $316 per night (USD)
VRBO
From $1268 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 $1268 per night (USD)
Expedia
From $707 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 $707 per night (USD)
VRBO
From $557 per night (USD)
Expedia
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 $557 per night (USD)
Expedia
From $404 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 $404 per night (USD)
VRBO
From $262 per night (USD)
Expedia
September Golf Cart Special
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 $262 per night (USD)
Expedia
From $1311 per night (USD)
VRBO
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 $1311 per night (USD)
VRBO
From $1346 per night (USD)
Expedia
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 $1346 per night (USD)
Expedia
From $456 per night (USD)
VRBO
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 $456 per night (USD)
VRBO
From $984 per night (USD)
Expedia
Bleuphoria - Rooftop Deck and Private Pool/Spa!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bleuphoria by AMI Locals 112 Elm Ave, Anna Maria, FL 34216 Welcome to Bleuphoria, a brand-new 4-bedroom, 4-bathroom vac ...
From $984 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
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Expedia
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 ...
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Expedia
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VRBO
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 ...
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VRBO
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Expedia
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 ...
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Expedia
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VRBO
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 ...
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VRBO
From $453 per night (USD)
Expedia
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 $453 per night (USD)
Expedia
From $838 per night (USD)
VRBO
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 $838 per night (USD)
VRBO
From $304 per night (USD)
Expedia
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 $304 per night (USD)
Expedia
From $608 per night (USD)
VRBO
September Golf Cart Special
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 $608 per night (USD)
VRBO
From $541 per night (USD)
Expedia
3 Bedroom Anna Maria Island North End Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
🏝️ Key Lime Cottage – Beachfront Bliss on Anna Maria Island Welcome to Key Lime Cottage, your dreamy Gulf-front hideawa ...
From $541 per night (USD)
Expedia
From $821 per night (USD)
VRBO
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 $821 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
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VRBO
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 ...
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VRBO
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VRBO
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, ...
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VRBO
From $554 per night (USD)
VRBO
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 $554 per night (USD)
VRBO
From $801 per night (USD)
Expedia
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 $801 per night (USD)
Expedia
From $732 per night (USD)
VRBO
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 $732 per night (USD)
VRBO
From $582 per night (USD)
Expedia
New Rental! Beautiful North End Canal Home with Pool close to the 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 $582 per night (USD)
Expedia
From $888 per night (USD)
VRBO
Waterfront Anna Maria Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Anna Maria Oasis, your perfect escape on beautiful Anna Maria Island! You’ve finally found the coastal char ...
From $888 per night (USD)
VRBO
From $466 per night (USD)
Expedia
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 $466 per night (USD)
Expedia
From $702 per night (USD)
VRBO
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)
VRBO
From $790 per night (USD)
Expedia
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 $790 per night (USD)
Expedia

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