Holiday rentals in Anna Maria Island
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Top-rated holiday rentals in Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Holmes Beach
4.96 out of 5 average rating, 157 reviewsSet AMI
This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.
7–14 Oct
Guest suite in Sarasota
4.98 out of 5 average rating, 101 reviewsMid-Century Modern Beach Getaway
Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!
15–22 Oct
Apartment in Redington Beach
4.97 out of 5 average rating, 455 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.
9–16 Nov
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Anna Maria Island holiday rentals
Other great holiday rentals in Anna Maria Island
Cottage in Holmes Beach
4.98 out of 5 average rating, 49 reviewsCalypso-an Anna Maria Island Oasis+Private Pool
17–24 Aug
Cottage in Cortez
4.81 out of 5 average rating, 91 reviewsTy's Canal Cottage
2–9 Sep
Apartment in Bradenton
4.92 out of 5 average rating, 51 reviewsAnna Maria Islands Neighbor (5min) + Walk to Bay!
3–10 Dec
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsami skyview
25 Sep – 2 Oct
Home in Anna Maria
5.0 out of 5 average rating, 11 reviewsLamantin- 2 bed/2bath North End, beach 2 min walk
29 Aug – 5 Sep
Home in Bradenton
5.0 out of 5 average rating, 7 reviewsThe "Love shack" Bungalow
19–26 Nov
Home in Anna Maria
4.87 out of 5 average rating, 23 reviewsSunKissed Cottage
23–30 Aug
Home in Anna Maria
5.0 out of 5 average rating, 57 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
7–14 Sep
Home in Holmes Beach
4.95 out of 5 average rating, 61 reviewsLuxury Beach house! Gulf Views, 86° Pool/Spa
24–31 Aug
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsAmie House Chef’s kitchen Fun pool - walk to beach
27 Oct – 3 Nov
Place to stay in Bradenton
4.96 out of 5 average rating, 24 reviewsSeas The Day By The Bay
17–24 Nov
Home in Holmes Beach
4.91 out of 5 average rating, 23 reviewsEnjoy AMI sunsets | Chic home w/ Saltwater pool!
6–13 Dec
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