Title: Anna Maria Island Guest Houses | Expedia.ca [Anna Maria Island Travel Guide](https://expedia.ca/Anna-Maria-Island.dx553248622847118534)[Hotels in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Hotels.d553248622847118534.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Vacation-Rentals.d553248622847118534.Travel-Guide-VacationRentals)[Flights to Anna Maria Island](https://expedia.ca/Cheap-Flights-To-Anna-Maria-Island.d553248622847118534.Travel-Guide-Flights)[Things to do in Anna Maria Island](https://expedia.ca/Things-To-Do-In-Anna-Maria-Island.d553248622847118534.Travel-Guide-Activities)[Anna Maria Island Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria-Island.d553248622847118534.Car-Rental-Guide)[Anna Maria Island Vacation Packages](https://expedia.ca/Anna-Maria-Island.d553248622847118534.Destination-Travel-Guides) ![Anna Maria Island, FL Pier ](https://images.trvl-media.com/place/553248622847118534/f6726703-de53-4942-875e-504e17e1a1f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Anna Maria Island - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Anna Maria Island guest houses ![Beach](https://images.trvl-media.com/lodging/108000000/107970000/107961700/107961678/b5771bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107961700/107961678/w1280h848x0y0-13f75f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107961700/107961678/6b08f3f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107961700/107961678/716349a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Plush K&Q Beds w/ Hot Tub near St Pete & Beaches [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Plush-KQ-Beds-W-Hot-Tub-Near-St-Pete-Beaches.h107961678.Hotel-Information) St. Petersburg 9.2/10 Wonderful (5) "Beautiful stay, very clean and comfy. Easy access. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $152 CA $344 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Plush-KQ-Beds-W-Hot-Tub-Near-St-Pete-Beaches.h107961678.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/31000000/30250000/30249600/30249599/81d899bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30250000/30249600/30249599/c91510d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/31000000/30250000/30249600/30249599/9c3c35ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/31000000/30250000/30249600/30249599/4bf8a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### With Oasis Shared Backyard [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-With-Oasis-Shared-Backyard.h30249599.Hotel-Information) Lake Maggiore Shore 8.4/10 Very good (35) "My stay was enjoyable. The owner was helpful with everything. Was great for the price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) william a. CA $130 CA $205 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-With-Oasis-Shared-Backyard.h30249599.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151105/e83f78dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151105/a57711d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151105/b6f59dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151105/3170a6e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage in Pass-A-Grille Beach, Dogs Ok [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Charming-Cottage-In-Pass-A-Grille-Beach.h66151105.Hotel-Information) Pass-a-Grille 9.6/10 Exceptional (31) "my sister and I enjoyed the space very much. the dogs enjoyed the nice fenced yard. thank you! lovely area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz E. CA $190 CA $441 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Charming-Cottage-In-Pass-A-Grille-Beach.h66151105.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/4ffe13e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/w3998h2258x0y0-57eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/w4000h2196x0y0-722bffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/f28582f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Siesta Key beach with a hot tub and a large garden [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) Sarasota 9.8/10 Exceptional (113) "This place is a must stay we could not fault the place they have thought of everything. Highly recommend this place." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Danny P. CA $156 CA $336 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99110000/99105000/99104982/604d7cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99110000/99105000/99104982/5986a429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99110000/99105000/99104982/a45a7ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99110000/99105000/99104982/998d21f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tree Top Getaway- Sleeps 4 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Tree-Top-Getaway-Sleeps-4.h99104982.Hotel-Information) Gulfport 9.6/10 Exceptional (5) "Fun little property for a weekend getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlotte C. CA $189 CA $323 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Tree-Top-Getaway-Sleeps-4.h99104982.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/2550bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/c634db4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/3d9028d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/193334ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quick and Easy Walk Downtown - Tons of Amenities [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) Central Sarasota 9.8/10 Exceptional (121) "Great stay! Convenient location, clean, comfortable, and well stocked. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $259 CA $387 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/3267e6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/852b9ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/e3a8d43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/4a7b0053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Guesthouse 1 mi from SRQ airport [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) Whitfield Estates 10/10 Exceptional (3) "This house was absolutely charming! I caught myself In complete awe of every detail - from the fun decor, to the thoughtful inclusion of all kitchen supplies to make a full meal, to the soft shower towels and the incredibly comfortable bed, bedding and pillows! Fantastic stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa D. CA $207 CA $364 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/90000000/89680000/89675700/89675683/aee0945e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89680000/89675700/89675683/d26238fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/90000000/89680000/89675700/89675683/9478ba1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89680000/89675700/89675683/4c84de66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Cozy.h89675683.Hotel-Information) Historic Old Northeast 9.6/10 Exceptional (14) "Great location!!Small space, but worked well for my wife and I.We had a great time, so no complaints." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph F. CA $129 CA $270 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Cozy.h89675683.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/f52cf6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/bbc3fdb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/9b40207f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/85eef7c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta key Guest House 5 star on the water Private [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) South Sarasota 9.0/10 Wonderful (18) "House was really comfortable, everything worked fine and was cozy. About 15 mins away from Siesta Key Beach..Would def come back. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giancarlo CA $207 CA $482 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/118000000/117960000/117958600/117958566/7482b240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117960000/117958600/117958566/caacd44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117960000/117958600/117958566/5b675d8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117960000/117958600/117958566/7f361c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Charming-PaG-Studio-Sunsets-Steps-2-Sand-Bikes.h117958566.Hotel-Information) Pass-a-Grille CA $167 CA $345 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Charming-PaG-Studio-Sunsets-Steps-2-Sand-Bikes.h117958566.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151104/99cce29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151104/67c6db3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151104/0f28edae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/67000000/66160000/66151200/66151104/80ebd0fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok! [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Hidden-Gem-Steps-To-Pass-A-Grille-Beach.h66151104.Hotel-Information) Pass-a-Grille 9.4/10 Exceptional (15) " Very close to the beach, several diners, safe and beautiful area. Highly recommend if you have a small group on your getaway, doesn’t get much better" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin R. CA $175 CA $450 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Hidden-Gem-Steps-To-Pass-A-Grille-Beach.h66151104.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05®ionId=553248622847118534&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FAnna-Maria-Island-Guest-Houses.d553248622847118534-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FAnna-Maria-Island-Guest-Houses.d553248622847118534-aaGuestHouses.Travel-Guide-Accommodation) ## Top Anna Maria Island Hotel Reviews ## Find out more about Anna Maria Island ## Anna Maria Island Guest Houses information | Number of reviews | | | ----------------- | ------------ | | Accommodation | Guest Houses | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### What is the nightly rate for a guest house in Anna Maria Island? ### What's the difference between a Anna Maria Island guest house and a B&B? ## Explore a world of travel with Expedia - 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