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

Search Guest Houses in Anna Maria Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Anna Maria Island guest houses

Property grounds

1. 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 ￥14,688
￥23,254 total
includes taxes & fees
Sep 7 - Sep 8
With Oasis Shared Backyard
Beach

2. 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 ￥16,126
￥40,451 total
includes taxes & fees
Sep 23 - Sep 24
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
Marina

3. 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 ￥17,790
￥33,719 total
includes taxes & fees
Sep 7 - Sep 8
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Beach

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 ￥19,078
￥54,554 total
includes taxes & fees
Sep 9 - Sep 10
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Beach

5. 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 ￥17,064
￥29,293 total
includes taxes & fees
Sep 7 - Sep 8
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Beach

6. 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 ￥15,231
￥44,853 total
includes taxes & fees
Sep 13 - Sep 14
Charming Cottage in Pass-A-Grille Beach, Dogs Ok
Outdoor dining

7. 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 ￥20,373
￥35,218 total
includes taxes & fees
Sep 7 - Sep 8
Tree Top Getaway- Sleeps 4
Beach

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, (140 reviews)
"Wonderful place to stay! Spacious, near Siesta Key beaches, and great pizza walking distance "
United States
Kari H.
The price is ￥17,579
￥39,093 total
includes taxes & fees
Sep 8 - Sep 9
Close to Siesta Key beach with a hot tub and a large garden
Terrace/patio

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 ￥23,439
￥55,707 total
includes taxes & fees
Sep 9 - Sep 10
Siesta key Guest House 5 star on the water Private
Beach

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 ￥12,188
￥29,611 total
includes taxes & fees
Sep 7 - Sep 8
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
Beach

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

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Madeira Beach
The price is ￥17,917
￥46,306 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

It's a Jungle Out There - Tropical Pool, Sunset Views, Game Room!

It's a Jungle Out There - Tropical Pool, Sunset Views, Game Room!

10/10 Excellent
"I’m"
Ashley P. 7-night trip
Posted 8 hours ago
It's a Jungle Out There - Tropical Pool, Sunset Views, Game Room!

Find out more about Anna Maria Island

Anna Maria Island Guest Houses information

Number of reviews
435
Accommodation
0 Guest Houses
Lowest Price
￥23,254
Highest Price
￥55,707

Explore a world of travel with Expedia