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.

Guest favourite

Home in Holmes Beach

4.96 out of 5 average rating, 157 reviews

Set 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

$404 SGD per night
Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 100 reviews

Mid-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

$155 SGD per night
Guest favourite

Apartment in Redington Beach

4.97 out of 5 average rating, 455 reviews

AmazingBeachCondo/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

$145 SGD per night

Popular amenities for Anna Maria Island holiday rentals

Other great holiday rentals in Anna Maria Island

Guest favourite

Cottage in Holmes Beach

4.98 out of 5 average rating, 49 reviews

Calypso-an Anna Maria Island Oasis+Private Pool

17–24 Aug

$587 SGD per night
Guest favourite

Cottage in Cortez

4.81 out of 5 average rating, 91 reviews

Ty's Canal Cottage

2–9 Sep

$169 SGD per night
Guest favourite

Apartment in Bradenton

4.92 out of 5 average rating, 51 reviews

Anna Maria Islands Neighbor (5min) + Walk to Bay!

3–10 Dec

$175 SGD per night
Guest favourite

Home in Anna Maria

5.0 out of 5 average rating, 28 reviews

ami skyview

25 Sep – 2 Oct

$1,341 SGD per night
Guest favourite

Home in Anna Maria

5.0 out of 5 average rating, 11 reviews

Lamantin- 2 bed/2bath North End, beach 2 min walk

29 Aug – 5 Sep

$553 SGD per night
Guest favourite

Home in Bradenton

5.0 out of 5 average rating, 7 reviews

The "Love shack" Bungalow

19–26 Nov

$175 SGD per night
Superhost

Home in Anna Maria

4.87 out of 5 average rating, 23 reviews

SunKissed Cottage

23–30 Aug

$1,237 SGD per night
Guest favourite

Home in Anna Maria

5.0 out of 5 average rating, 57 reviews

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

7–14 Sep

$1,050 SGD per night
Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 61 reviews

Luxury Beach house! Gulf Views, 86° Pool/Spa

24–31 Aug

$1,238 SGD per night
Guest favourite

Home in Anna Maria

5.0 out of 5 average rating, 28 reviews

Amie House Chef’s kitchen Fun pool - walk to beach

27 Oct – 3 Nov

$1,376 SGD per night
Guest favourite

Place to stay in Bradenton

5.0 out of 5 average rating, 23 reviews

Seas The Day By The Bay

17–24 Nov

$159 SGD per night
Guest favourite

Home in Holmes Beach

4.91 out of 5 average rating, 23 reviews

Enjoy AMI sunsets | Chic home w/ Saltwater pool!

6–13 Dec

$253 SGD per night

Destinations to explore