Vacation rentals with a pool in Anna Maria Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Anna Maria Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite

Condo in Holmes Beach

4.99 out of 5 average rating, 122 reviews

Beach Escape - Make Memories on Anna Maria Island!

Relax and unwind at this updated beach condo with a heated pool and outdoor shower overlooking a peaceful park. Very short stroll through the park and then about 150 steps to the white sand beach. Quaint condo community with only 8 units total. Wonderful couple escape or family getaway. Sleeps 2-6 guests. Private, covered 2 car parking. Laundry in unit. Storage room with beach wagon, beach chairs, and Weber grill. Location is a hidden gem close to everything you need for a relaxing island stay.

Oct 24 ā€“ 31

$229 per night
Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and Ā½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Oct 23 ā€“ 30

$462 per night
Guest favorite

Home in Holmes Beach

4.99 out of 5 average rating, 153 reviews

Captain's Quarters at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. Youā€™ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Spa maintains same temperature as pool. Captains Quarters also has Private patio!

Oct 12 ā€“ 19

$395 per night

Popular amenities for Anna Maria Island rentals with a pool

House rentals with a pool

Guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 123 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Aug 25 ā€“ Sep 1

$391 per night
Superhost

Home in Holmes Beach

4.8 out of 5 average rating, 25 reviews

Walk to beach | Anna Maria home w/ pool | Pets ok!

Sep 28 ā€“ Oct 5

$161 per night
Guest favorite

Home in Holmes Beach

5.0 out of 5 average rating, 46 reviews

Private Luxurious Ground Level Home

Sep 16 ā€“ 23

$350 per night
Guest favorite

Home in Anna Maria

4.99 out of 5 average rating, 74 reviews

CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B

Aug 22 ā€“ 29

$310 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 57 reviews

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

Sep 7 ā€“ 14

$678 per night
Superhost

Home in Anna Maria

4.92 out of 5 average rating, 36 reviews

Island in the Sun

Sep 18 ā€“ 25

$427 per night
Superhost

Home in Holmes Beach

5.0 out of 5 average rating, 16 reviews

AMI Villa by Beach Boutique Rentals

Sep 25 ā€“ Oct 2

$376 per night
Superhost

Home in Anna Maria

4.87 out of 5 average rating, 23 reviews

SunKissed Cottage

Aug 23 ā€“ 30

$918 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 74 reviews

Manatee Harbour - heated pool, with canal access

$577 per night
Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 37 reviews

True beach front home - 3 beds/2 bath, heated pool

Sep 29 ā€“ Oct 6

$616 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 28 reviews

Amie House Chefā€™s kitchen Fun pool - walk to beach

Oct 27 ā€“ Nov 3

$883 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 19 reviews

Stunning new 4 bed/4.5 bath home with heated pool

Dec 13 ā€“ 20

$971 per night

Condo rentals with a pool

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 142 reviews

1 BR direct beachfront! Now available May 22-27!

Oct 30 ā€“ Nov 6

$135 per night
Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 200 reviews

Sunset Beach Condo in Treasure Island

Nov 10 ā€“ 17

$114 per night
Guest favorite

Condo in Redington Beach

4.94 out of 5 average rating, 356 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

Dec 12 ā€“ 19

$102 per night
Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 143 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Mar 19 ā€“ 26

$304 per night
Superhost

Condo in North Redington Beach

4.81 out of 5 average rating, 271 reviews

Beachside Mini-Condo on North Redington Beach!

Sep 20 ā€“ 27

$109 per night
Guest favorite

Condo in Treasure Island

4.99 out of 5 average rating, 150 reviews

Spectacular beach to bay views from this resort.

Sep 12 ā€“ 19

$170 per night
Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 146 reviews

Sunset Studio on the Coast

Nov 30 ā€“ Dec 7

$275 per night
Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 167 reviews

Shorewalk full condo IMG Beaches Anna Maria

Aug 31 ā€“ Sep 7

$126 per night
Guest favorite

Condo in Holmes Beach

4.98 out of 5 average rating, 107 reviews

NEW listing on AMI! Walk to fabulous beach front!

Feb 1 ā€“ 8

$250 per night
Guest favorite

Condo in Redington Beach

4.89 out of 5 average rating, 150 reviews

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA

Aug 8 ā€“ 15

$78 per night
Superhost

Condo in Holmes Beach

4.86 out of 5 average rating, 108 reviews

Steps from the beach

Aug 22 ā€“ 29

$219 per night
Guest favorite

Condo in Redington Beach

4.9 out of 5 average rating, 144 reviews

2min walk to the beach/pool, BBQ/great area, RO110

Aug 26 ā€“ Sep 2

$99 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Anna Maria Island
  6. Rentals with pools