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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Check prices for these dates

Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Anna Maria Island guest houses

Beach nearby

1. 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 £197
includes taxes & fees
21 Sept - 22 Sept
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
Beach nearby

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, (43 reviews)
"Perfect place for a getaway"
United States
Barbara F.
The price is £239
includes taxes & fees
26 Sept - 27 Sept
Charming Cottage in Pass-A-Grille Beach, Dogs Ok
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 £165
includes taxes & fees
8 Oct - 9 Oct
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Beach

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 £139
includes taxes & fees
21 Sept - 22 Sept
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Beach nearby

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 £280
includes taxes & fees
24 Sept - 25 Sept
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Outdoor dining

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 £175
includes taxes & fees
21 Sept - 22 Sept
Tree Top Getaway- Sleeps 4
Beach nearby, sun-loungers, beach towels

7. 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 £191
includes taxes & fees
21 Sept - 22 Sept
Close to Siesta Key beach with a hot tub and a large garden
Terrace/patio

8. 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 £271
includes taxes & fees
1 Oct - 2 Oct
Siesta key Guest House 5 star on the water Private
Beach

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.
The price is £139
includes taxes & fees
24 Sept - 25 Sept
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
On the beach

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

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Madeira Beach
The price is £214
includes taxes & fees
24 Sept - 25 Sept
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

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

10/10 Excellent
"It was a great location close to the beach, very clean and perfect size for a weekend getaway"
Trinity 2-night trip
Posted 1 hour ago
Driftwood at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Guest Houses information

Number of reviews
5,601
Accommodation
0 Guest Houses
Lowest Price
£85
Highest Price
£415

Frequently asked questions

What is the nightly rate for a guest house in Anna Maria Island?
Rates for Anna Maria Island guest houses vary, but travelers can find great-value prices from £85 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Anna Maria Island guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Anna Maria Island guest house and a B&B?
A guest house in Anna Maria Island is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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