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, 121 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 – 31

€ 301 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 ½ 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 – 30

€ 556 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. You’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 – 19

€ 512 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 – Sep 1

€ 497 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 – Oct 5

€ 222 per night
Guest favorite

Home in Holmes Beach

5.0 out of 5 average rating, 46 reviews

Private Luxurious Ground Level Home

Sep 16 – 23

€ 441 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 – 29

€ 393 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 – 14

€ 842 per night
Superhost

Home in Anna Maria

4.92 out of 5 average rating, 36 reviews

Island in the Sun

Sep 18 – 25

€ 557 per night
Superhost

Home in Holmes Beach

5.0 out of 5 average rating, 16 reviews

AMI Villa by Beach Boutique Rentals

Sep 25 – Oct 2

€ 490 per night
Superhost

Home in Anna Maria

4.87 out of 5 average rating, 23 reviews

SunKissed Cottage

Aug 23 – 30

€ 1,008 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 74 reviews

Manatee Harbour - heated pool, with canal access

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 – Oct 6

€ 774 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 28 reviews

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

Oct 27 – Nov 3

€ 1,114 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 – 20

€ 1,200 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 – Nov 6

€ 182 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 – 17

€ 147 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 – 19

€ 131 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 – 26

€ 357 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 – 27

€ 138 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 – 19

€ 216 per night
Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 146 reviews

Sunset Studio on the Coast

Nov 30 – Dec 7

€ 343 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 – Sep 7

€ 162 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 – 8

€ 309 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 – 15

€ 110 per night
Superhost

Condo in Holmes Beach

4.86 out of 5 average rating, 108 reviews

Steps from the beach

Aug 22 – 29

€ 270 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 – Sep 2

€ 132 per night

Destinations to explore