Anna Maria Island Holiday Rentals

Compare Villas, Resorts, & Rentals in Anna Maria Island, Florida, USA

Canal-front Gem with Pool and Hot Tub in Anna Maria
House
Canal-front Gem with Pool and Hot Tub in Anna Maria
From ZA R15,705 per night
|
10.0 (8 Reviews)
2 Bedrooms 6 Guests
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Anna Maria Island Beach Palms 6B
Apartment
Anna Maria Island Beach Palms 6B
From ZA R9,860 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
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New Coastal Calm/Holmes Beach Pool Ocean Views
House
Coastal Calm/Holmes Beach Pool Ocean Views
From ZA R33,842 per night
New
3 Bedrooms 8 Guests
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Sunset Connection - Gulf Place
Apartment
Sunset Connection - Gulf Place
From ZA R10,765 per night
|
10.0 (8 Reviews)
3 Bedrooms 6 Guests
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New Acacia Breeze by Duncan Real Estate
House
Acacia Breeze by Duncan Real Estate
From ZA R16,404 per night
New
4 Bedrooms 10 Guests
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Cheerful Pelican on Anna Maria Island
House
Cheerful Pelican on Anna Maria Island
From ZA R4,906 per night
|
10.0 (5 Reviews)
2 Bedrooms 6 Guests
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The S 2a 1 Bedroom Villa by RedAwning
House
The S 2a 1 Bedroom Villa by RedAwning
From ZA R2,323 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
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Slo M'Ocean
House
Slo M'Ocean
From ZA R3,640 per night
|
10.0 (4 Reviews)
2 Bedrooms 6 Guests
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New Waterfront Anna Maria Oasis
House
Waterfront Anna Maria Oasis
From ZA R13,834 per night
New
3 Bedrooms 8 Guests
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Blue Wave Villa East
Villa
Blue Wave Villa East
From ZA R6,743 per night
|
10.0 (3 Reviews)
2 Bedrooms 4 Guests
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New Tropical Paradise: 4BR Island Home w/Pool & Bay Views
House
Tropical Paradise: 4BR Island Home w/Pool & Bay Views
From ZA R12,189 per night
New
4 Bedrooms 8 Guests
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Bayview Condo B
House
Bayview Condo B
From ZA R6,154 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
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Villa #7 AMI Lime Fish
Villa
Villa #7 AMI Lime Fish
From ZA R13,434 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
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New Jersey Gal by Duncan Real Estate
House
Jersey Gal by Duncan Real Estate
From ZA R10,783 per night
New
3 Bedrooms 8 Guests
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Villa #3 Seahorse
Villa
Villa #3 Seahorse
From ZA R10,834 per night
|
10.0 (3 Reviews)
1 Bedroom 4 Guests
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New LivingGood by Duncan Real Estate
House
LivingGood by Duncan Real Estate
From ZA R9,695 per night
New
3 Bedrooms 6 Guests
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Fish, Swim and Unwind Anna Maria Apt Steps to Beach
Apartment
Fish, Swim and Unwind Anna Maria Apt Steps to Beach
From ZA R5,304 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
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New Sea La Vie by Duncan Real Estate
House
Sea La Vie by Duncan Real Estate
From ZA R8,157 per night
New
3 Bedrooms 6 Guests
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EV Charger, Endless Summer by SeaBreeze Vacation
House
EV Charger, Endless Summer by SeaBreeze Vacation
From ZA R27,111 per night
|
10.0 (2 Reviews)
7 Bedrooms 16 Guests
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New Mermaid's Haven, perfect getaway
Condo
Mermaid's Haven, perfect getaway
From ZA R7,717 per night
New
3 Bedrooms 8 Guests
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Mermaid Manor
House
Mermaid Manor
From ZA R26,140 per night
|
10.0 (2 Reviews)
4 Bedrooms 8 Guests
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New Barefoot Boho- Bungalow on Anna Maria Island
House
Barefoot Boho- Bungalow on Anna Maria Island
From ZA R6,503 per night
New
1 Bedroom 4 Guests
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The 19th Hole - 238
House
The 19th Hole - 238
From ZA R23,107 per night
|
10.0 (2 Reviews)
3 Bedrooms 8 Guests
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New Dans Florida Condos Sea Scape at Runaway Bay
Condo
Dans Florida Condos Sea Scape at Runaway Bay
From ZA R5,627 per night
New
2 Bedrooms 6 Guests
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New Dans Florida Condos Four Palms at Runaway Bay
Condo
Dans Florida Condos Four Palms at Runaway Bay
From ZA R5,627 per night
New
2 Bedrooms 5 Guests
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AM I Dreaming
House
AM I Dreaming
From ZA R16,121 per night
|
10.0 (2 Reviews)
3 Bedrooms 8 Guests
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New Dans Florida Condos Blue Fin at Runaway Bay
Condo
Dans Florida Condos Blue Fin at Runaway Bay
From ZA R5,627 per night
New
2 Bedrooms 6 Guests
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La Casa Karen
Apartment
La Casa Karen
From ZA R14,457 per night
|
10.0 (2 Reviews)
3 Bedrooms 6 Guests
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Sand And Sea 109 A
House
Sand And Sea 109 A
From ZA R12,307 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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Pelican Villa
House
Pelican Villa
From ZA R11,267 per night
|
10.0 (2 Reviews)
4 Bedrooms 8 Guests
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Tranquil AMI Resort Unit 1 all amenities! Central Holmes Beach
Apartment
Tranquil AMI Resort Unit 1 all amenities! Central Holmes Beach
From ZA R3,604 per night
10.0 (120 Reviews)
1 Bedroom 4 Guests
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Golf Cart included! Short walk to the Beach on the Peaceful North End
House
Golf Cart included! Short walk to the Beach on the Peaceful North End
From ZA R8,841 per night
|
10.0 (2 Reviews)
4 Bedrooms 8 Guests
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MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
Villa
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
From ZA R5,764 per night
10.0 (119 Reviews)
2 Bedrooms 4 Guests
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Southern Breeze 3
House
Southern Breeze 3
From ZA R7,384 per night
|
10.0 (2 Reviews)
1 Bedroom 6 Guests
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The S 2b 2 Bedroom Villa by RedAwning
House
The S 2b 2 Bedroom Villa by RedAwning
From ZA R3,848 per night
|
9.4 (3 Reviews)
1 Bedroom 2 Guests
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The perfect view for your beach getaway
House
The perfect view for your beach getaway
From ZA R5,859 per night
|
10.0 (2 Reviews)
2 Bedrooms 5 Guests
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Tradewinds Beach Resort
Condo
Tradewinds Beach Resort
From ZA R4,507 per night
9.2 (380 Reviews)
1 Bedroom 4 Guests
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Beach and Bay Getaway
House
Beach and Bay Getaway
From ZA R4,923 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa
Villa
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa
From ZA R5,093 per night
10.0 (112 Reviews)
2 Bedrooms 5 Guests
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Starfish Beach Cottage #3
House
Starfish Beach Cottage #3
From ZA R7,367 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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Bungalow On The Bayou (Best Location on the Island)
House
Bungalow On The Bayou (Best Location on the Island)
From ZA R3,791 per night
10.0 (110 Reviews)
2 Bedrooms 4 Guests
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*Steps to Beach, Heated Pool, Balcony, Amenities*
Apartment
*Steps to Beach, Heated Pool, Balcony, Amenities*
From ZA R3,738 per night
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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Beachfront Paradise
House
Beachfront Paradise
From ZA R97,541 per night
|
10.0 (1 Review)
8 Bedrooms 16 Guests
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Bayfront Paradise (AMIL)
House
Bayfront Paradise (AMIL)
From ZA R41,325 per night
|
10.0 (1 Review)
4 Bedrooms 8 Guests
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SUGAR REEF "A" Just Steps from the Gulf!
House
SUGAR REEF "A" Just Steps from the Gulf!
From ZA R4,309 per night
10.0 (104 Reviews)
2 Bedrooms 4 Guests
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The Big Yellow House
House
The Big Yellow House
From ZA R34,530 per night
|
10.0 (1 Review)
5 Bedrooms 10 Guests
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Sits ON the Sand! Paradise!
Condo
Sits ON the Sand! Paradise!
From ZA R8,396 per night
10.0 (101 Reviews)
1 Bedroom 4 Guests
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Dans Florida Condos Sea Dream at Runaway Bay
Condo
Dans Florida Condos Sea Dream at Runaway Bay
From ZA R5,276 per night
|
10.0 (99 Reviews)
2 Bedrooms 6 Guests
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Ami Du Soleil Steps To The Beach, Heated Pool
House
Ami Du Soleil Steps To The Beach, Heated Pool
From ZA R26,886 per night
|
10.0 (1 Review)
1 Bedroom 8 Guests
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About Casai's Private Villas and Holiday Rentals in Anna Maria Island

Discover more than 5660 vacation rentals available in Anna Maria Island. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Anna Maria Island.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Anna Maria Island, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Anna Maria Island. On average, places to stay near Anna Maria Island offer 1365.62 ft², with nightly prices averaging ZA R10,138.

With Casai, finding and comparing holiday rentals in Anna Maria Island is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other Places to Stay in Anna Maria Island, FL


Manatee Public Beach 7,088 Properties
West Coast Surf Shop 7,027 Properties
AMI Paddleboard Adventures 7,013 Properties
Sweet Pea's 6,991 Properties
Island Gallery West 6,981 Properties
Holmes Beach Beaches 6,960 Properties
Key Royale 5,699 Properties
Aluna Wellness Center & Spa 5,649 Properties
Holmes Beach 1,819 Properties
Bradenton Beach 1,319 Properties
Anna Maria 1,102 Properties
Ilexhurst 139 Properties

Frequently Asked Questions About Anna Maria Island?

What are the top holiday rentals in Anna Maria Island?

How many Casai.co.za holiday rentals are available in Anna Maria Island?

As of 2025, Casai boasts over 5660 properties listed in the Anna Maria Island area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Anna Maria Island.

Nearby Neighborhood (2)

Neighborhood Property Count
Ilexhurst Vacation Rentals in Florida 139
Key Royale Vacation Rentals in Florida 5699

There are 5660 Anna Maria Island, FL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Anna Maria Island