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.
Condo in Holmes Beach
4.99 out of 5 average rating, 121 reviewsBeach 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
Home in Anna Maria
4.93 out of 5 average rating, 152 reviewsPrivate 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
Home in Holmes Beach
4.99 out of 5 average rating, 153 reviewsCaptain'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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Anna Maria Island rentals with a pool
House rentals with a pool
Home in Holmes Beach
4.97 out of 5 average rating, 123 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Aug 25 – Sep 1
Home in Holmes Beach
4.8 out of 5 average rating, 25 reviewsWalk to beach | Anna Maria home w/ pool | Pets ok!
Sep 28 – Oct 5
Home in Holmes Beach
5.0 out of 5 average rating, 46 reviewsPrivate Luxurious Ground Level Home
Sep 16 – 23
Home in Anna Maria
4.99 out of 5 average rating, 74 reviewsCHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
Aug 22 – 29
Home in Anna Maria
5.0 out of 5 average rating, 57 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Sep 7 – 14
Home in Anna Maria
4.92 out of 5 average rating, 36 reviewsIsland in the Sun
Sep 18 – 25
Home in Holmes Beach
5.0 out of 5 average rating, 16 reviewsAMI Villa by Beach Boutique Rentals
Sep 25 – Oct 2
Home in Anna Maria
4.87 out of 5 average rating, 23 reviewsSunKissed Cottage
Aug 23 – 30
Home in Anna Maria
5.0 out of 5 average rating, 74 reviewsManatee Harbour - heated pool, with canal access
Home in Holmes Beach
4.95 out of 5 average rating, 37 reviewsTrue beach front home - 3 beds/2 bath, heated pool
Sep 29 – Oct 6
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsAmie House Chef’s kitchen Fun pool - walk to beach
Oct 27 – Nov 3
Home in Anna Maria
5.0 out of 5 average rating, 19 reviewsStunning new 4 bed/4.5 bath home with heated pool
Dec 13 – 20
Condo rentals with a pool
Condo in Indian Shores
4.96 out of 5 average rating, 142 reviews1 BR direct beachfront! Now available May 22-27!
Oct 30 – Nov 6
Condo in St. Pete Beach
4.92 out of 5 average rating, 200 reviewsSunset Beach Condo in Treasure Island
Nov 10 – 17
Condo in Redington Beach
4.94 out of 5 average rating, 356 reviewsBeach Condo, Heated Pool, 2 Minute Walk to Ocean
Dec 12 – 19
Condo in Longboat Key
4.93 out of 5 average rating, 143 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Mar 19 – 26
Condo in North Redington Beach
4.81 out of 5 average rating, 271 reviewsBeachside Mini-Condo on North Redington Beach!
Sep 20 – 27
Condo in Treasure Island
4.99 out of 5 average rating, 150 reviewsSpectacular beach to bay views from this resort.
Sep 12 – 19
Condo in Longboat Key
4.97 out of 5 average rating, 146 reviewsSunset Studio on the Coast
Nov 30 – Dec 7
Condo in Bradenton
4.98 out of 5 average rating, 167 reviewsShorewalk full condo IMG Beaches Anna Maria
Aug 31 – Sep 7
Condo in Holmes Beach
4.98 out of 5 average rating, 107 reviewsNEW listing on AMI! Walk to fabulous beach front!
Feb 1 – 8
Condo in Redington Beach
4.89 out of 5 average rating, 150 reviewsSWEET BEACH RETREAT - REDINGTON BEACH FLORIDA
Aug 8 – 15
Condo in Holmes Beach
4.86 out of 5 average rating, 108 reviewsSteps from the beach
Aug 22 – 29
Condo in Redington Beach
4.9 out of 5 average rating, 144 reviews2min walk to the beach/pool, BBQ/great area, RO110
Aug 26 – Sep 2
Destinations to explore
- St Petersburg Vacation rentals
- Sarasota Vacation rentals
- Tampa Vacation rentals
- Key West Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Rentals with pools United States
- Rentals with pools Florida
- Rentals with pools Florida
- Cottage rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- Beachfront rentals Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- Beach condo rentals Anna Maria Island
- Rentals with a patio Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Villa rentals Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Condo rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Waterfront rentals Anna Maria Island
- Rentals with lake access Anna Maria Island
- Rentals with a washer and dryer Anna Maria Island
- Wheelchair accessible rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- House rentals Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Beach house rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with pools Kissimmee
- Rentals with pools Tampa
- Rentals with pools Manatee County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom