An aerial view of a coastal town with a long pier extending into turquoise waters.

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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Our top choices for Anna Maria Island guest houses

A marina with boats docked, a wooden dock, and a clear sky.

1. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Whitfield Estates
7.4 out of 10, Good, (6 reviews)
"Looking for a couple nights close to Anna Maria Island without being ON the island. Turns out we were here once before and didnt realize it was the same place. Love the "Back Yard" surprises"
United States
Susan B.
The price is NZ$381
includes taxes & fees
22 Oct - 23 Oct
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
An aerial view of a coastal town with a long sandy beach, a marina, and residential buildings.

2. Charming Cottage in Pass-A-Grille Beach, Dogs Ok

Charming Cottage in Pass-A-Grille Beach, Dogs Ok
Pass-a-Grille
9.6 out of 10, Exceptional, (46 reviews)
"Perfect place for a getaway"
United States
Barbara F.
The price is NZ$577
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage in Pass-A-Grille Beach, Dogs Ok
A beach with a sandy shore, a few people, and buildings in the background.

3. Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
Pass-a-Grille
9.2 out of 10, Wonderful, (10 reviews)
"Perfect little space. Clean, comfortable and you just can't beat the location. Lisa was a joy to work with. "
United States
Laura P.
The price is NZ$521
includes taxes & fees
11 Nov - 12 Nov
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
An aerial view of a coastal town with a long sandy beach, a marina, and residential buildings.

4. A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Pass-a-Grille
9.6 out of 10, Exceptional, (17 reviews)
"Great location for walking to beach and local restaurants. Prefect size for my family of four."
United States
Melissa G
The price is NZ$757
includes taxes & fees
27 Oct - 28 Oct
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
A wooden outdoor bar area with a clear view of the backyard, including a wooden fence, palm trees, and a small pool.

5. With Oasis Shared Backyard

With Oasis Shared Backyard
Lake Maggiore Shore
8.2 out of 10, Very good, (36 reviews)
"Just stayed onenight. Will stay again"
United States
Glen V.
The price is NZ$266
includes taxes & fees
15 Oct - 16 Oct
With Oasis Shared Backyard
A lifeguard tower with a blue umbrella and a yellow flag on a sandy beach.

6. Close to Siesta Key beach with a hot tub and a large garden

Close to Siesta Key beach with a hot tub and a large garden
Sarasota
9.8 out of 10, Exceptional, (141 reviews)
"Wonderful place to stay! Spacious, near Siesta Key beaches, and great pizza walking distance "
United States
Kari H.
The price is NZ$439
includes taxes & fees
17 Oct - 18 Oct
Close to Siesta Key beach with a hot tub and a large garden
A covered outdoor deck with a ceiling fan, wooden railing, and a seating area with cushions.

7. Siesta key Guest House 5 star on the water Private

Siesta key Guest House 5 star on the water Private
South Sarasota
8.8 out of 10, Excellent, (21 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
The price is NZ$524
includes taxes & fees
19 Oct - 20 Oct
Siesta key Guest House 5 star on the water Private
A beach with gentle waves and a sunset.

8. Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Central Sarasota
9.8 out of 10, Exceptional, (140 reviews)
"Stephanie is a great host. The coach house is very clean and comfortable and all of the extras available to us made the trip so good - like beach chairs, umbrellas, e-bikes. It’s a great location with Main Street walkable and fantastic beaches by car."
United Kingdom
Liz
The price is NZ$376
includes taxes & fees
27 Oct - 28 Oct
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
A beach at sunset with waves and a colorful sky.

9. Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
Historic Old Northeast
9.8 out of 10, Exceptional, (18 reviews)
"The property was great and exactly what we needed! The location was within walking distance to so may great spots and the guide Lisa provided was super helpful."
United States
Phoebe A.
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
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.
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Top Anna Maria Island Hotel Reviews

Captain's Quarters at Anna Maria Island Inn

Captain's Quarters at Anna Maria Island Inn

10/10 Excellent
"This place was so convenient and beautiful nice amenities when we got there we got there early and they gave us a wristband to let us use their lounge chairs and swim at their beach while we wait for the room to be ready and then the room is walking distance from the beach. It’s so nice. Loved it."
Shawn 3-night trip
Posted 9 hours ago
Captain's Quarters at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Guest Houses information

Number of reviews
435
Accommodation
0 Guest Houses
Lowest Price
NZ$266
Highest Price
NZ$757

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