Anna Maria Cottage Rentals

KAYAK searches hundreds of travel sites at once for cottage deals in Anna Maria

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Anna Maria cottage rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$93 - $372$372 - $650$650 - $929$929 - $1,207$1,207+ per night

Search by freebies

Free breakfastFree parkingFree cancellationFree internetFree airport shuttle

Most recommended cottage rentals in Anna Maria

Show all
Chic Sarasota Cottage Near Beaches and Downtown! - Sarasota - Living room
Chic Sarasota Cottage Near Beaches and Downtown!
Sarasota, FL
9.9Wonderful(16)
Cottage
$230+
Check availability
Sundance Cottage - Anna Maria - Dining room
Sundance Cottage
Anna Maria, FL
9.2Wonderful(45)
Cottage
$654+
Check availability
Mangrove Cottage - Anna Maria - Pool
Mangrove Cottage
Anna Maria, FL
7.8Good(23)
Cottage
$631+
Check availability
The Seashell Cottage by RedAwning - Anna Maria - Living room
The Seashell Cottage by RedAwning
Anna Maria, FL
8.6Very good(21)
Cottage
$564+
Check availability
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum - Sarasota - Balcony
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Sarasota, FL
9.5Wonderful(22)
Cottage
$198+
Check availability
Coastal Gem! - Sarasota - Living room
Coastal Gem!
Sarasota, FL
9.9Wonderful(30)
Cottage
$252+
Check availability
Close to Nathan Benderson-Owl's Nest Eco-Cottage - Sarasota - Bedroom
Close to Nathan Benderson-Owl's Nest Eco-Cottage
Sarasota, FL
8.6Very good(3)
Cottage
$193+
Check availability
The Cottage Next Door Best Downtown location in Sarasota - Sarasota - Living room
The Cottage Next Door Best Downtown location in Sarasota
Downtown
10Wonderful(19)
Cottage
$393+
Check availability
Storybook Cottage in a Dream Location - Private Pool, Near Siesta & More - Sarasota - Pool
Storybook Cottage in a Dream Location - Private Pool, Near Siesta & More
Sarasota, FL
9.8Wonderful(38)
Cottage
$143+
Check availability
Book Me Baby! Pool, Pet-Friendly Paradise Near Downtown Sarasota - Sarasota - Patio
Book Me Baby! Pool, Pet-Friendly Paradise Near Downtown Sarasota
Sarasota, FL
9.0Wonderful(14)
Cottage
$210+
Check availability
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill! - Sarasota - Living room
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
Sarasota, FL
9.8Wonderful(43)
Cottage
$244+
Check availability
Beautiful Guest House Near the Beach with Private Pool! - Anna Maria - Bedroom
Beautiful Guest House Near the Beach with Private Pool!
Anna Maria, FL
10Wonderful(4)
Cottage
$606+
Check availability
Charming cottage in quiet area, close to beach & bay. - Anna Maria - Living room
Charming cottage in quiet area, close to beach & bay.
Anna Maria, FL
9.7Wonderful(138)
Cottage
$433+
Check availability
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool - Sarasota - Bedroom
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Sarasota, FL
9.8Wonderful(67)
Cottage
$694+
Check availability
Blue Heron Cottage - Anna Maria Island - Anna Maria - Beach
Blue Heron Cottage - Anna Maria Island
Anna Maria, FL
10Wonderful(50)
Cottage
$403+
Check availability
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe! - Sarasota - Bedroom
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Sarasota, FL
8.8Very good(13)
Cottage
$158+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
May
$1,108
$656
Cheapest month to stay with an average 72% drop in price.
Most expensive month to stay with an average 137% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Anna Maria vacation rental deals

  • For the cheapest cottage rental in Anna Maria, try to visit during the low season and outside of main travel peaks. The cheapest rates can be found in January and October.
  • The cheapest night of the week to rent a cottage in Anna Maria is Monday. On the other hand, the most expensive is Thursday.

FAQs when Booking a cottage in Anna Maria

  • How much is a cottage rental for a week in Anna Maria?

    The average price for a weekly Anna Maria cottage rental found by KAYAK users in the last 2 weeks is $6,854 ($979/night). Though this can obviously vary depending on the time of year of your stay and when you make the booking.

  • How much is a cottage rental for a month in Anna Maria?

    The average price for a monthly Anna Maria cottage rental found by KAYAK users in the last 2 weeks is $23,793 ($793/night).

Where to stay in Anna Maria?

Our map will help you find the perfect place to stay in Anna Maria by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Anna Maria