1. What are the top vacation rentals in Anna Maria?

To simplify your decision-making process amidst the plethora of options in Anna Maria, why not reserve a few nights at one of the highest-rated vacation rentals on SunSki Resorts? Beautiful, Gulf-Front Home on Bean Point-Halcyon House Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis Dragonfly - Southern charm on the North end of Anna Maria Island Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue! 2nd House from the Beach with No Roads to Cross Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point. Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach! Charming House with Private Heated Pool, Lanai. Great location to beach & shops Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat Do you love the beach?

Anna Maria Vacation Rentals & Ski-in/Ski-out Homes

Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

From US $489

10.0 (4 Reviews)

House

Beautifully Updated Home North End of Island, Screen lanai Grill and beach gear

Air Conditioner
Parking
TV

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From US $684

9.0 (1 Review)

House

21 Palms on Anna Maria

Air Conditioner
Pet Friendly
View

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Waves- steps from the beach with a water view

From US $1,014

10.0 (9 Reviews)

House

Waves- steps from the beach with a water view

Air Conditioner
Parking
Pet Friendly

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Salt Dreams: 1 Block to Beach! Pool, Spa, Games, Rooftop Deck by Anna Maria Life Vacation Rentals

From US $2,409

9.4 (3 Reviews)

House

Salt Dreams: 1 Block to Beach! Pool, Spa, Games, Rooftop Deck by Anna Maria Life Vacation Rentals

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Pool

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From US $830

9.5 (2 Reviews)

House

Beach to Bay Getaway

Air Conditioner
Pet Friendly
Pool

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From US $327

9.6 (5 Reviews)

House

Charming Cottage Near Bay and Beach

Air Conditioner
Parking
TV

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From US $1,629

8.8 (5 Reviews)

House

Rooftop Views! Pool, Spa and Game Room!

Air Conditioner
Parking
Pet Friendly

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Anna Maria Home with Pool and Rooftop Deck! 5-min Walk to Beach - Coconut Breeze

From US $869

9.8 (8 Reviews)

House

Anna Maria Home with Pool and Rooftop Deck! 5-min Walk to Beach - Coconut Breeze

Air Conditioner
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AMI Escape! Swim-Up Bar, Ping Pong, Spa and Walk to Beach

From US $1,183

9.6 (4 Reviews)

House

AMI Escape! Swim-Up Bar, Ping Pong, Spa and Walk to Beach

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Luxury Places to Stay in Anna Maria

Over 1546+ Luxury Places to Stay in or Near Anna Maria

From US $6,114

New

Resort

The Rod and Reel Resort

Air Conditioner
TV
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From US $3,569

New

House

Bay View Beauty

Parking
Pet Friendly
Pool

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Beachfront! 2 Masters with Beachfront Views! Pool - Games!

From US $3,506

10.0 (31 Reviews)

House

Beachfront! 2 Masters with Beachfront Views! Pool - Games!

Air Conditioner
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Pool

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Bikini Bottom: 5 Hole Mini Golft, Games,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life

From US $3,482

10.0 (28 Reviews)

House

Bikini Bottom: 5 Hole Mini Golft, Games,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life

Air Conditioner
Parking
Pet Friendly

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From US $3,289

9.4 (6 Reviews)

House

Brand New Luxury Home! Canal Front with Pool, Spa, and Rooftop Deck with Stunnin

Air Conditioner
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Pet Friendly

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Dolphin Tales: Pool, Bay Views & Private Beach by Anna Maria Life Vacation Rentals

From US $3,285

9.2 (25 Reviews)

House

Dolphin Tales: Pool, Bay Views & Private Beach by Anna Maria Life Vacation Rentals

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Pool

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From US $3,284

New

House

Banyan Beach - 104 Beach Ave

Parking
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The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals

From US $3,165

New

House

The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals

Air Conditioner
Parking
Pet Friendly

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Under the Sun! Rooftop Deck, Pool and Spa!

From US $3,139

9.0 (4 Reviews)

House

Under the Sun! Rooftop Deck, Pool and Spa!

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Top-Rated Vacation Rentals with a Pool in Anna Maria

Over 1231+ Top-Rated Vacation Rentals with a Pool in or Near Anna Maria

Dragonfly - Southern charm on the North end of Anna Maria Island

From US $1,133

10.0 (187 Reviews)

House

Dragonfly - Southern charm on the North end of Anna Maria Island

Air Conditioner
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Pool

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Charming House with Private Heated Pool, Lanai. Great location to beach & shops

From US $403

10.0 (166 Reviews)

House

Charming House with Private Heated Pool, Lanai. Great location to beach & shops

Air Conditioner
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Pool

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From US $954

10.0 (146 Reviews)

House

Spectacular Beachfront House with Pool

Air Conditioner
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AMI North End Private Heated Pool. 1.2 Block to Gulf Beach!

From US $358

10.0 (143 Reviews)

House

AMI North End Private Heated Pool. 1.2 Block to Gulf Beach!

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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

From US $508

10.0 (142 Reviews)

House

Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

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Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!

From US $2,107

10.0 (138 Reviews)

House

Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!

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4.9 rated Island rental with exceptional testimonials for over 10 years!

From US $427

10.0 (131 Reviews)

House

4.9 rated Island rental with exceptional testimonials for over 10 years!

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Pet Friendly

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Luxury Upscale Beach Home Gulf of Mexico, Private Heated Pool/Spa. Opt. Golfcart

From US $960

10.0 (130 Reviews)

House

Luxury Upscale Beach Home Gulf of Mexico, Private Heated Pool/Spa. Opt. Golfcart

Air Conditioner
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Pet Friendly

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Private Pool - Seaglass Cottage by SeaBreeze Vacation

From US $412

10.0 (127 Reviews)

Cottage

Private Pool - Seaglass Cottage by SeaBreeze Vacation

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Pet-Friendly Vacation Rentals in Anna Maria

Over 507+ Pet-Friendly Vacation Rentals in or Near Anna Maria

Luxurious Shangri-La Home with Pool, Spa, & Rooftop Deck on Anna Maria Island

From US $3,068

10.0 (1 Review)

House

Luxurious Shangri-La Home with Pool, Spa, & Rooftop Deck on Anna Maria Island

Air Conditioner
Parking
Pet Friendly

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From US $1,878

New

House

Total Package

Pet Friendly
Pool
Accessibility

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From US $1,504

10.0 (20 Reviews)

House

Serendipity Gulfront- gulf beach front

Air Conditioner
Parking
Pet Friendly

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From US $1,436

10.0 (3 Reviews)

House

Brand New Luxury Home, Incredible Rooftop Deck and Pool! - Total Package

Air Conditioner
Parking
Pet Friendly

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From US $891

8.1 (21 Reviews)

House

Anna Maria's Finest

Air Conditioner
Pet Friendly
Pool

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Charming 3-bedroom house in Anna Maria with Private Pool & Spa

From US $668

10.0 (1 Review)

House

Charming 3-bedroom house in Anna Maria with Private Pool & Spa

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Pet Friendly

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Beach Bliss - Water View, heated pool, putt putt

From US $1,024

10.0 (5 Reviews)

House

Beach Bliss - Water View, heated pool, putt putt

Air Conditioner
Parking
Pet Friendly

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Beach Cottage on Elm! Home with Pool, Spa, Rooftop Deck and Gulf Views

From US $1,426

10.0 (9 Reviews)

House

Beach Cottage on Elm! Home with Pool, Spa, Rooftop Deck and Gulf Views

Air Conditioner
Parking
Pet Friendly

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From US $1,037

9.8 (10 Reviews)

House

Waves- steps from the beach with a water view

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Large Vacation Homes & Villas in Anna Maria

Over 311+ Large Vacation Homes & Villas in or Near Anna Maria

Mandalay Bay - Enjoy waterfront luxury at its finest!

From US $2,266

10.0 (1 Review)

House

Mandalay Bay - Enjoy waterfront luxury at its finest!

Air Conditioner
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Pool

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From US $974

8.5 (2 Reviews)

Villa

Bay Vista at Bayside Bungalow

Pet Friendly
Pool
Security/Safety

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Island Gem B 2 Bedroom Villa by RedAwning

From US $222

New

Villa

Island Gem B 2 Bedroom Villa by RedAwning

Air Conditioner
Pet Friendly
TV

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150 Feet to the Beach! Large Beach Home with Heated Pool! - Sunset Paradise

From US $1,299

8.8 (8 Reviews)

House

150 Feet to the Beach! Large Beach Home with Heated Pool! - Sunset Paradise

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From US $1,408

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House

Beach A La Mode - 211

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Large Private Beach Home! Private Pool, Spa and Outdoor Lighting

From US $1,577

9.2 (17 Reviews)

House

Large Private Beach Home! Private Pool, Spa and Outdoor Lighting

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Coastal Retreat with Beach Views, Pool and Serene Outdoor

From US $854

9.2 (9 Reviews)

House

Coastal Retreat with Beach Views, Pool and Serene Outdoor

Air Conditioner
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Canal-Front Oasis with Private Dock, Pool, Near Beach and Shops - Aqua Cove

From US $631

9.2 (32 Reviews)

House

Canal-Front Oasis with Private Dock, Pool, Near Beach and Shops - Aqua Cove

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Beach a la Mode | Luxury Canal Front Home on AMI w/Private Pool & Spa

From US $2,057

9.4 (3 Reviews)

House

Beach a la Mode | Luxury Canal Front Home on AMI w/Private Pool & Spa

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Wheelchair Accessible Vacation Homes in Anna Maria

Over 168+ Wheelchair Accessible Vacation Homes in or Near Anna Maria

North End of Anna Maria Island! Private Pool and Spa, One Block to the Beach! -

From US $797

9.4 (21 Reviews)

House

North End of Anna Maria Island! Private Pool and Spa, One Block to the Beach! -

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From US $844

5.0 (1 Review)

House

Mangrove Cottage

Air Conditioner
Pet Friendly
Pool

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From US $1,814

9.6 (40 Reviews)

House

luxury beachfront/heated pool

Air Conditioner
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From US $1,372

10.0 (2 Reviews)

House

Brand New home with Incredible Rooftop Deck and Pool! - Just Breathe

Air Conditioner
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From US $385

9.0 (8 Reviews)

House

Getaway on Gladiolus

Air Conditioner
Pet Friendly
Pool

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Coastal home near the shopping district and Gulf beaches

From US $1,817

10.0 (1 Review)

House

Coastal home near the shopping district and Gulf beaches

Air Conditioner
Parking
Pool

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Anna Maria Escape! Pool, Spa, and Canal Views - Our Tern

From US $746

9.8 (10 Reviews)

House

Anna Maria Escape! Pool, Spa, and Canal Views - Our Tern

Air Conditioner
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From US $2,686

9.8 (22 Reviews)

House

The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals

Air Conditioner
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Pool

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From US $1,627

9.4 (30 Reviews)

House

Serendipity - Beach Front 4/3

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Anna Maria Resorts and Airbnb Homes Under $200

Over 19+ Anna Maria Resorts and Airbnb Homes Under $200

2nd-floor condo across the street from the beach with heated pool, balcony, W/D

From US $142

10.0 (3 Reviews)

Condo

2nd-floor condo across the street from the beach with heated pool, balcony, W/D

Air Conditioner
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From US $182

New

Apartment

21 Palms Unit A

Air Conditioner
Pet Friendly
Wheelchair Accessible

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From US $159

New

Condo

Minnow 2 2 Bedroom Villa by RedAwning

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Ground-floor duplex with fast WiFi, central AC & grill

From US $174

9.2 (30 Reviews)

Apartment

Ground-floor duplex with fast WiFi, central AC & grill

Air Conditioner
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From US $167

New

House

AMI Retreat - 746 Jacaranda

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Dog-friendly family home with WiFi, central AC, private W/D - close to beach

From US $192

8.4 (32 Reviews)

Apartment

Dog-friendly family home with WiFi, central AC, private W/D - close to beach

Air Conditioner
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Pet Friendly

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Bayou Hideaway: 2 BR, 1 BA Condominium in Anna Maria, Sleeps 4

From US $159

9.4 (3 Reviews)

Condo

Bayou Hideaway: 2 BR, 1 BA Condominium in Anna Maria, Sleeps 4

Air Conditioner
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Come experience Anna Maria Island the way it is supposed to be!

From US $175

6.0 (2 Reviews)

House

Come experience Anna Maria Island the way it is supposed to be!

Air Conditioner
Pet Friendly
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☀️🌊🐟❤️Love Shack on the Water (Most Desirable Location on AMI)

From US $190

10.0 (39 Reviews)

Condo

☀️🌊🐟❤️Love Shack on the Water (Most Desirable Location on AMI)

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Instantly Bookable Vacation Homes in Anna Maria

Over 1008+ Instantly Bookable Vacation Homes in or Near Anna Maria

Beachfront Home with Amazing Deck and Beach Views! -Low Tide

From US $1,053

10.0 (3 Reviews)

House

Beachfront Home with Amazing Deck and Beach Views! -Low Tide

Air Conditioner
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BeachFront 4/3/Amazing Views plus hot tub

From US $1,150

9.4 (28 Reviews)

House

BeachFront 4/3/Amazing Views plus hot tub

Air Conditioner
Parking
Pet Friendly

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Bo’s Beach Bungalow! Steps to Beach, Shops and Dining

From US $322

9.4 (8 Reviews)

House

Bo’s Beach Bungalow! Steps to Beach, Shops and Dining

Air Conditioner
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Salty Sister: Stunning Beachfront Vacation Home with Heated Pool, Steps from Anna Maria Island Beach

From US $2,485

10.0 (8 Reviews)

House

Salty Sister: Stunning Beachfront Vacation Home with Heated Pool, Steps from Anna Maria Island Beach

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From US $453

8.4 (25 Reviews)

House

The Wee Cottage | House in Anna Maria

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Updated Home with Heated Pool and Grill! 1 Minute Walk to Beach!

From US $565

8.6 (12 Reviews)

House

Updated Home with Heated Pool and Grill! 1 Minute Walk to Beach!

Air Conditioner
Parking
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AMI Escape! Dog Friendly with Pool, Ping Pong and Tiki Bar

From US $564

9.2 (9 Reviews)

House

AMI Escape! Dog Friendly with Pool, Ping Pong and Tiki Bar

Air Conditioner
Parking
Pet Friendly

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Adorable Duplex on AMI! With Pool, Near Bean Point Beach

From US $352

9.2 (51 Reviews)

House

Adorable Duplex on AMI! With Pool, Near Bean Point Beach

Air Conditioner
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Pool

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From US $1,038

9.0 (2 Reviews)

House

Elevated North-End Home Near the Beach!

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About Anna Maria Vacation Rentals

Explore over 1555 vacation rentals in Anna Maria with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Anna Maria for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Anna Maria. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Anna Maria tailored to your preferences. On average, these rentals offer 1670.36 ft² of space, and are priced at an average of US $902 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Anna Maria at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Anna Maria

Type	Count
Vacation Homes	1379
Villas	37
Cottages	36
Holiday Apartments	29
Cabin Rentals	1

Use these Quick Filters to Find a Vacation Rental in Anna Maria

★ Pro Tip: Discover Your Ideal Vacation Rental in Anna Maria with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Anna Maria, FL

View the weather forecast for Anna Maria before booking your Anna Maria Vacation Rentals to confirm your best time to go.

December - February

High 75°F Low 58°F

March - May

High 86°F Low 61°F

June - August

High 91°F Low 76°F

September - November

High 89°F Low 63°F

Top Attractions Around Anna Maria, FL

Sunski offers a large selection of top attractions around Anna Maria . Research things to do on your vacation before you visit Anna Maria.

Anna Maria Beach

Bayfront Park

Island Players

Anna Maria Island Museum and Historical Park

Anna Maria City Pier

Historic Green Village

AMI Outfitters Coastal Gear & Apparel

Lido Beach

John's Pass Village & Boardwalk

Tropicana Field

Salvador Dali Museum

St. Armands Circle

IMG Academy

Vinoy Park

Fort De Soto Park

Coquina Beach

Eckerd College

Sarasota Jungle Gardens

Mote Marine Laboratory & Aquarium

Sarasota Memorial Hospital

Other Places to Stay in Anna Maria, FL

Island Players 3,995 Properties

Anna Maria Island Museum and Historical Park 3,926 Properties

AMI Outfitters Coastal Gear & Apparel 3,914 Properties

Historic Green Village 3,914 Properties

Anna Maria City Pier 3,846 Properties

Bayfront Park 3,631 Properties

Anna Maria Beach 3,331 Properties

Complexes around Anna Maria, FL

Anna Maria Island Beach 62 Properties

Island Gem 4 Properties

Southern Magnolia 2 Properties

The Lady Fish 2 Properties

Cs Sarasota 1 Properties

Gladiolus The Water 1 Properties

Holmes Beach 1 Properties

Seascapes 1 Properties

Shore Nokomis 1 Properties

Frequently Asked Questions About Anna Maria?

What are the top vacation rentals in Anna Maria?

When organizing your trip to Anna Maria, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Anna Maria. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Anna Maria?

Uncover 815 vacation rentals boasting private pools near Anna Maria. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in Anna Maria are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Anna Maria. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Anna Maria?

Discover the ideal vacation rental in Anna Maria with SunSki Resorts™. We provide an extensive selection of over 1555 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Anna Maria.