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Our top choices for Anna Maria holiday homes

1. Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!

Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!
Anna Maria
10.0 out of 10, Exceptional, (30 reviews)
"Great property!"
United States
Jessica S.
The price is £464
includes taxes & fees
1 Dec - 2 Dec
Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!

2. Private Pool / Spa Home - Steps to Anna Maria Island Beach

Private Pool / Spa Home - Steps to Anna Maria Island Beach
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"We came in for a girls trip and the home and location were perfect. The house is truly steps from the beach and has everything you need. We also enjoyed to pool and patio for coffee and drinks every day."
United States
Holly F.
The price is £557
includes taxes & fees
2 Dec - 3 Dec
Private Pool / Spa Home - Steps to Anna Maria Island Beach

3. Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stay! Proximity to the beach cannot be beat! Staff was so nice and helpful. Can’t wait to stay again!"
United States
Anne B.
The price is £461
includes taxes & fees
29 Nov - 30 Nov
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

4. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Great sister stayHouse was perfect, pool was enjoyed by us all after a day a the beachMorning and evening at the pool We will be back for our next get together"
United States
Cheryl M.
The price is £568
includes taxes & fees
2 Dec - 3 Dec
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

5. Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Anna Maria
9.2 out of 10, Wonderful, (63 reviews)
"Great place- close to the beach!"
United States
Jaymi R.
The price is £514
includes taxes & fees
8 Nov - 9 Nov
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

6. The Hideaway ~ Near Beach ~ Coastal Cottage

The Hideaway ~ Near Beach ~ Coastal Cottage
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great. So close to the beach a 3 min walk. We loved everything about it."
United States
JASON G.
The price is £615
includes taxes & fees
16 Nov - 17 Nov
The Hideaway ~ Near Beach ~ Coastal Cottage

7. Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave

Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"."
United States
Richard
The price is £546
includes taxes & fees
1 Dec - 2 Dec
Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave

8. Kiwi Cottage ~ Near Beach ~ Heated Pool

Kiwi Cottage ~ Near Beach ~ Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Perfect location! Walking distance to beaches, shops and restaurants! The pool was an added bonus"
United States
Christopher
The price is £585
includes taxes & fees
28 Nov - 29 Nov
Kiwi Cottage ~ Near Beach ~ Heated Pool

9. Mermaid’s Purse ~ Near Beach ~ Heated Pool

Mermaid’s Purse ~ Near Beach ~ Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location and great service. Thanks for allowing us to make life long memories with our kids!"
United States
Magen S.
The price is £635
includes taxes & fees
29 Nov - 30 Nov
Mermaid’s Purse ~ Near Beach ~ Heated Pool

10. Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Anna Maria
7.8 out of 10, Good, (91 reviews)
"Absolutely loved it and would love to stay there again."
United States
Marcus S.
The price is £617
includes taxes & fees
15 Nov - 16 Nov
Waterfront dog-friendly home with heated private pool, dock, views, and lanai

11. Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!

Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!
Anna Maria
10.0 out of 10, Exceptional, (40 reviews)
"Cute and enjoyable cottage and property manager/staff were amazing and made us feel like we were at home! Everything you need is in kitchen and property is in an excellent location."
United States
April B.
The price is £602
includes taxes & fees
30 Nov - 1 Dec
Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!

12. Island beach cottage, Pool, bikes, beach gear, moments from the sand!

Island beach cottage, Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Great location with everything you need for a wonderful beach trip!"
United States
Erin V.
The price is £540
includes taxes & fees
30 Nov - 1 Dec
Island beach cottage, Pool, bikes, beach gear, moments from the sand!

13. AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf

AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Nice size rooms. Pool was in the shade but very clean. All around a great stay"
United States
Kelly F.
The price is £947
includes taxes & fees
30 Nov - 1 Dec
AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf

14. Palm Paradise ~ Near Beach ~ Heated Pool

Palm Paradise ~ Near Beach ~ Heated Pool
Anna Maria
The price is £768
includes taxes & fees
29 Nov - 30 Nov
Palm Paradise ~ Near Beach ~ Heated Pool

15. Birdsong ~ North End ~ Private Heated Pool

Birdsong ~ North End ~ Private Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"The property was exactly as advertised. We loved our time at this property and how clean it was. The private pool was so enjoyable and complimented our time at the beach that is just down the street during our stay."
United States
Aaron C.
The price is £678
includes taxes & fees
8 Nov - 9 Nov
Birdsong ~ North End ~ Private Heated Pool

16. 4 King Beds + Guest House • Heated Pool/Spa

4 King Beds + Guest House • Heated Pool/Spa
Anna Maria
The price is £717
includes taxes & fees
15 Nov - 16 Nov
4 King Beds + Guest House • Heated Pool/Spa

17. BEACHFRONT, NOV. SPECIALS PRIVATE BEACH WATERFRONT, Bring your Dog Awesome views

BEACHFRONT, NOV. SPECIALS PRIVATE BEACH WATERFRONT, Bring your Dog Awesome views
Anna Maria
9.6 out of 10, Exceptional, (220 reviews)
"Fantastic stay! Extremely clean and the location is perfect. The private beach was a great addition to our stay."
United States
Anonymous traveller
The price is £665
includes taxes & fees
9 Nov - 10 Nov
BEACHFRONT, NOV. SPECIALS PRIVATE BEACH WATERFRONT, Bring your Dog Awesome views

18. Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
ANNA MARIA
9.6 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay. Great location, and beautiful water view. Would defiantly stay again"
United States
Tina H.
The price is £513
includes taxes & fees
8 Nov - 9 Nov
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

19. AMI Canal-Front Luxury • Heated Pool /Spa & Boat Dock

AMI Canal-Front Luxury • Heated Pool /Spa & Boat Dock
Anna Maria
10.0 out of 10, Exceptional, (4 reviews)
"The house was perfect for our stay at AMI"
United States
Kevin D.
The price is £938
includes taxes & fees
2 Dec - 3 Dec
AMI Canal-Front Luxury • Heated Pool /Spa & Boat Dock

20. Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa

Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa
Anna Maria
9.8 out of 10, Exceptional, (22 reviews)
"Great house! Great host!"
United States
Katie K.
The price is £1,216
includes taxes & fees
29 Nov - 30 Nov
Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Anna Maria

This laid-back island paradise offers white-sand beaches where dolphins often swim close to shore during sunset walks. Rent a bike to explore the Pine Avenue shops, then grab fresh grouper sandwiches at Rod and Reel Pier.

A coastal town with a long pier extending into the turquoise sea, a sandy beach, and residential buildings along the shore.

Top reviews in Anna Maria

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