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

Search Guest Houses in Anna Maria Island

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Our top choices for Anna Maria Island guest houses

1. With Oasis Shared Backyard

With Oasis Shared Backyard
Lake Maggiore Shore
8.2 out of 10, Very Good, (36 reviews)
"We arrived and the outside area was very messy compared to the photos. Also the camper stunk of sewage so bad we could not continue to stay. Inside the camper there were bugs in the shower. When contacted we did not get a refund and basically were told there was nothing they can do. The owner had not connected the sewage correctly which caused the smell, they did fix it but it was too late. "
United States
madison c.
The price is ¥14,941
¥23,655 total
includes taxes & fees
Aug 29 - Aug 30
With Oasis Shared Backyard

2. 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 ¥17,310
¥33,205 total
includes taxes & fees
Aug 23 - Aug 24
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

3. 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, (42 reviews)
"Perfect place for a getaway"
United States
Barbara F.
The price is ¥15,493
¥46,102 total
includes taxes & fees
Aug 23 - Aug 24
Charming Cottage in Pass-A-Grille Beach, Dogs Ok

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

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Central Sarasota
9.8 out of 10, Exceptional, (137 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 ¥16,523
¥28,856 total
includes taxes & fees
Aug 23 - Aug 24
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

5. 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 ¥21,038
¥58,131 total
includes taxes & fees
Aug 27 - Aug 28
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

6. Tree Top Getaway- Sleeps 4

Tree Top Getaway- Sleeps 4
Gulfport
9.0 out of 10, Wonderful, (8 reviews)
"Fun little property for a weekend getaway!"
United States
Charlotte C.
The price is ¥20,724
¥36,460 total
includes taxes & fees
Aug 23 - Aug 24
Tree Top Getaway- Sleeps 4

7. 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 ¥19,328
¥46,629 total
includes taxes & fees
Sep 7 - Sep 8
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

8. 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, (138 reviews)
"We loved our stay here!! The place was clean and comfortable. Definitely coming back! "
United States
Cresta Blanca
The price is ¥17,882
¥39,607 total
includes taxes & fees
Aug 25 - Aug 26
Close to Siesta Key beach with a hot tub and a large garden

9. 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 ¥23,843
¥57,143 total
includes taxes & fees
Aug 24 - Aug 25
Siesta key Guest House 5 star on the water Private

10. 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.
The price is ¥11,190
¥29,619 total
includes taxes & fees
Aug 25 - Aug 26
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

11. Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Madeira Beach
The price is ¥62,090
¥103,726 total
includes taxes & fees
Sep 17 - Sep 18
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
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

Find out more about Anna Maria Island

Anna Maria Island Guest Houses information

Number of reviews
433
Accommodation
0 Guest Houses
Lowest Price
¥23,655
Highest Price
¥103,726

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