Anna Maria Island

Welcome to Anna Maria Island, FL

Where are you going?

Choose a destination Close
Where are you going?
Aruba

Eagle Beach

Aruba Breeze Condominiums

Divi Village

Jardines del Mar

Oceania Residence

Sunset Residence

Malmok

Noord

Aruba's Life Residences

Gold Coast

Little Paradise

Little Sea

Palma Real

Palmaruba Condos

Summerside Condos

The Cove Condominium

Tierra del Sol

Wariruri Condos

Oranjestad

Ponton

Santa Cruz

Savaneta

Florida

Bradenton

Clearwater

Belleair

Clermont

Windsor Cay Resort

Dania Beach

Davenport

Bahama Bay Resort

Festival Resort

Solterra Resort

The Azur Resort

The Fountains at Champions Gate

Windsor Island Resort

Davie

Deerfield Beach

Fort Lauderdale

Haines City

Balmoral Resort

Hallandale Beach

Hollywood

Kissimmee

Bella Vida Resort

ChampionsGate Resort

Club Cortile

Cumbrian Lakes Resort

Emerald Island Resort

Encore Resort

Happy Trails

Indian Ridge

Indian Wells

Legacy Dunes

Margaritaville Resort

Paradise Palms Resort

Reunion Resort & Golf Club

Solara Resort

Sonoma Resort

Storey Lake Resort

Summer Flower

Terra Verde

The Cove East

The Villas at Somerset

Veranda Palms Resort Orlando

Villas at Laguna Bay

Westside at Tuscany

Windsor Hills Resort

Windsor Palms Resort

Windsor at Westside Resort

Largo

Lighthouse Point

Miami

Brickell

Four Seasons Hotel Miami

The Club at Brickell Bay

Downtown Miami

227 NE 2nd Street

North Miami Beach

Oakland Park

Orlando

Blue Heron Beach Resort

Paradiso Grande

StaySky Suites

The Enclave

Vista Cay Resort

Parkland

Plantation

Pompano Beach

Seminole

Southwest Ranches

Tampa

West Palm Beach

Spain

Texas

Houston

Med Center

The Heights

W 23rd Street

United Arab Emirates
Next

Pick a date Close

December 2025
S	M	T	W	T	F	S
	01	02	03	04	05	06
07	08	09	10	11	12	13
14	15	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum
21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum
28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

January 2026
S	M	T	W	T	F	S
				01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum
04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum
11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum
18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum
25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

February 2026
S	M	T	W	T	F	S
01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum
08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum
15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum
22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum

March 2026
S	M	T	W	T	F	S
01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum
08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum
15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum
22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum
29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

April 2026
S	M	T	W	T	F	S
			01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum
05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum
12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum
19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum
26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum

May 2026
S	M	T	W	T	F	S
					01 01 2 nights minimum	02 02 2 nights minimum
03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum
10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum
17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum
24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum
31 31 2 nights minimum

June 2026
S	M	T	W	T	F	S
	01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum
07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum
14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum
21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum
28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum

July 2026
S	M	T	W	T	F	S
			01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum
05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum
12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum
19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum
26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

August 2026
S	M	T	W	T	F	S
						01 01 2 nights minimum
02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum
09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum
16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum
23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum
30 30 2 nights minimum	31 31 2 nights minimum

September 2026
S	M	T	W	T	F	S
		01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum
06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum
13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum
20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum
27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum

October 2026
S	M	T	W	T	F	S
				01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum
04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum
11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum
18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum
25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

November 2026
S	M	T	W	T	F	S
01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum
08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum
15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum
22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum
29 29 2 nights minimum	30 30 2 nights minimum

December 2026
S	M	T	W	T	F	S
		01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum
06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum
13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum
20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum
27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

January 2027
S	M	T	W	T	F	S
03 03 2 nights minimum					01 01 2 nights minimum	02 02 2 nights minimum
	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum
10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum
17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum
24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum
31 31 2 nights minimum

February 2027
S	M	T	W	T	F	S
	01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum
07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum
14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum
21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum
28 28 2 nights minimum

March 2027
S	M	T	W	T	F	S
	01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum
07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum
14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum
21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum
28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum	31 31 2 nights minimum

April 2027
S	M	T	W	T	F	S
				01 01 2 nights minimum	02 02 2 nights minimum	03 03 2 nights minimum
04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum	09 09 2 nights minimum	10 10 2 nights minimum
11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum	16 16 2 nights minimum	17 17 2 nights minimum
18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum	23 23 2 nights minimum	24 24 2 nights minimum
25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum	30 30 2 nights minimum

May 2027
S	M	T	W	T	F	S
						01 01 2 nights minimum
02 02 2 nights minimum	03 03 2 nights minimum	04 04 2 nights minimum	05 05 2 nights minimum	06 06 2 nights minimum	07 07 2 nights minimum	08 08 2 nights minimum
09 09 2 nights minimum	10 10 2 nights minimum	11 11 2 nights minimum	12 12 2 nights minimum	13 13 2 nights minimum	14 14 2 nights minimum	15 15 2 nights minimum
16 16 2 nights minimum	17 17 2 nights minimum	18 18 2 nights minimum	19 19 2 nights minimum	20 20 2 nights minimum	21 21 2 nights minimum	22 22 2 nights minimum
23 23 2 nights minimum	24 24 2 nights minimum	25 25 2 nights minimum	26 26 2 nights minimum	27 27 2 nights minimum	28 28 2 nights minimum	29 29 2 nights minimum
30 30 2 nights minimum	31 31 2 nights minimum

Add guests Close

Who's coming?

Adults (12+)
Ages 13 and above

Children
Ages 0 - 12

Dogs

Bringing an assistance animal?

Previous

Find a Casiola vacation home in more than 40 different destinations worldwide

Discover all our amazing Casiola vacation rentals in the area

Why you should book directly with Casiola vacation homes in Anna Maria Island, FL

Instant booking

Book our vacation rentals in Clearwater FL super fast via our secured website.

Lowest price guarantee

Booking direct with Casiola guarantees the best rate. Save up to 15% off other booking sites.

Free cancellation

Cancel stress-free up to 14 days before arrival date.

Design your own experience

Customize your vacation the way you want. Enjoy the perks of true comfort and luxury with all of our guest services.

Early check in

Late check out

Hassle free car hire

Heated swimming pool

Extraordinary housekeeping

Ticket service

Grocery delivery

Guests love their stay in Anna Maria Island, FL

0/10

on Booking.com

0/5

Airbnb Cleanliness rating

0/10

on Hotels.com

“Your home was incredibly inviting, comfortable, and the perfect spot for our family’s Disney trip. We spent two of our days resting at your home and soaking in the amenities (pool, lazy river, slides, happy hour). Your property management company was stellar and was the cherry on top of the experience! I was worried as our plane didn’t land till 11:30 p.m. and had an early morning at Disney the…

Rich

Huge space with everything you need. Felt safe. Plenty of parking. Bed was great. Master bath was huge.

Victoria G.

This unit was amazing, looked exactly as described. Large and lots of space and we loved having the extra half bath. 10/10 would stay here again

Jill

Beautiful home in Aruba with very responsive host. Close to things to do, restaurants, and shopping. Safe, gated community. Large home with plenty of space for the 9 of us!

Heather

The villa was beautiful. It had everything we needed. It was spacious. The pool was cleaned regularly which was great because of the rain prior to our arrival. One of the best villas I have stayed at in Aruba. The location couldn’t have been better. The windows and front door pad lock were super. Couldn’t have been happier.

Sandra

Huge space with everything you need. Felt safe. Plenty of parking. Bed was great. Master bath was huge.

Victoria G.

Great place. The PS5 CONSOLE was very useful for entertaining the kids. Great place!! The PS5 CONSOLE was very useful for entertaining the kids. The furniture of the living room was recently replaced for armchairs and legitimate leather SOFA.

Erico L.

Amazing villa so spacious. Ideal location only a short easy drive to Disney attractions. Staff helpful us Brits not used to posh plastic box next to front door, to put in rubbish thought it was a seat! Washer and drier were easy to use and very useful. Property clean and good air conditioning. Pool well looked after, clear water a bit cool for the adults, even with great weather over…

Gale V.

Rich

We had an exceptional experiencing renting, now our 4th time, with Casiola rentals in Orlando, Florida! Customer service was extremely responsive to each of our requests, including assistance getting us into the rental property early and sending maintenance out in a timely manner for a minor issue which was promptly rectified. The unit was exactly as described and quite spacious. Amenities were exceptional and location superb!

Kevin A.

Beautiful home in Aruba with very responsive host. Close to things to do, restaurants, and shopping. Safe, gated community. Large home with plenty of space for the 9 of us!

Heather

The home was comfortable and located in a very safe neighborhood . In addition, it is centrally located to many of the most popular beaches and nightlife. We also enjoyed many of the amenities that the home offered including the pool. We would most definitely stay in the home again and would like to thank our hosts, Stuart and Julia, for making our stay in Aruba a memorable one.

Alejandro

Sandra T.

This unit was amazing, looked exactly as described. Large and lots of space and we loved having the extra half bath. 10/10 would stay here again

Jill

Staying in a vacation home in Anna Maria Island, FL

Anna Maria Island, Florida, is a picturesque slice of paradise located just off the coast of Bradenton, known for its charming beach-town atmosphere, stunning turquoise waters, and powder-soft white sand beaches. With its laid-back vibe and friendly locals, Anna Maria Island is the ideal destination for anyone looking to escape the hustle and bustle of everyday life. Spend your days relaxing on beautiful beaches like Bean Point, a tranquil spot perfect for swimming, shelling, and unforgettable sunsets. Explore the island on two wheels by renting a bike and cruising along scenic paths, or hop on the Anna Maria Island Trolley to visit quirky shops, galleries, and cozy cafes scattered throughout the island’s three charming towns—Anna Maria, Holmes Beach, and Bradenton Beach. For an adventure, go paddleboarding, kayaking, or even dolphin-watching along the crystal-clear waters surrounding the island, or cast a line at the historic Rod & Reel Pier and try your luck fishing with breathtaking views of Tampa Bay.

When visiting Anna Maria Island, there’s no better place to stay than Casiola vacation homes, offering unmatched comfort, convenience, and style. Rather than squeezing into a crowded hotel room, you’ll enjoy spacious homes with fully equipped kitchens, luxurious amenities, and inviting living spaces just steps away from the island’s pristine beaches. Whether you’re traveling with family, friends, or planning a romantic getaway, a Casiola home provides the perfect setting to unwind, recharge, and soak in the island’s charming coastal lifestyle. After a sunny day of exploring, shopping, or relaxing on the beach, you’ll love coming home to your private, cozy retreat, making your Anna Maria Island vacation unforgettable.