Anna Maria Island Rentals With A Pool

We have a great selection of Anna Maria Island rentals with a pool, some even have a hot tub! For the utmost in relaxation and convenience, take a look at our vacation homes with swimming pools and hot tubs included. Relax in privacy with any of our vacation homes and condos with swimming pools. Although it’s always pleasant to swim in warm ocean waters, sometimes you want to take a quick dip at your home or hotel if there’s a pool readily available. That’s exactly what you’ll get with our exclusive Anna Maria Island rentals with a pool. These gorgeous homes offer numerous amenities for a long and relaxing stay on the island while allowing you to swim with more privacy than the local beaches. With multiple pool vacation homes to choose from in varying sizes, we promise that you will find ideal accommodations for your group or family.

My Rentals (0)

313 Island Walk

Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[313 64th]

Bradenton Beach Club A

Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront

[Bradbc-A]

Sandy Point 205

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach

[SP205]

Bradenton Beach Club 249

Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[BradBC249]

Gulf Watch 104

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[GW104]

Shorewalk 101-1 - 4675

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[ShoreW101-1]

Anna Maria Island Club 45

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC45]

Pelican Cove 4

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[PC 4]

Sunbow Bay 212

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[SBB212]

3011 Ave E-1

Bed & Bath: 4/2 Sleeps: 8 Location: Holmes Beach View: Near Beach

[3011-1]

LaPlayita Condo 5

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach

[LAPLAY5]

510 Bayview

Bed & Bath: 5/5 Sleeps: 10 Location: Holmes Beach View: Canal

[510Bayview]

Coquina Moorings 201

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[CM-201]

518 71st St--Palm Paradise

Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Canal

[518 71st]

Harbor Lane 1 Serenity

Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach

[HarborLane1]

Cayman 104

Bed & Bath: 2/2 Sleeps: 5 Location: Holmes Beach View: Near Beach

[Cayman 104]

217 84th Street

Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[217 84TH]

Sandy Point Cove 114

Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach View: Near Beach

[SPC114]

Gulf View 103

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[GV103]

Anna Maria Island Club 46

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC46]

Harbor Lane 4 Harmony

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[HarborLane4]

Pelican Cove 9

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Bayfront

[PC 9]

811Audubon

Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton View:

[811Audubon]

Club Bamboo South 119 Studio

Bed & Bath: Studio/1 Sleeps: 3 Location: Bradenton Beach View: Beachfront

[Bamboo 119]

Martinique 306 South

Bed & Bath: 2/2 Sleeps: 5 Location: Holmes Beach View: Beachfront

[Mart306]

7310 Holmes Blvd

Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach

[7310 Holmes]

707 N Bay The Shell House

Bed & Bath: 3/2½ Sleeps: 6 Location: Anna Maria View: Near Beach

[707BAY]

Bay View Condo C

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[BVC]

Club Bamboo South 220 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 220]

Coquina Beach Club 102

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront

[CBC102]

Pine Bay Forest 7521

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[Pine Bay]

Runaway Bay 205

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[RAB205]

Pelican Cove 2

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[PC 2]

3011 Ave E-3

Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach

[3011-3]

Anna Maria Island Club 26

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC26]

313 Palm Ave

Bed & Bath: 2/1 Sleeps: 4 Location: Anna Maria View: Near Beach

[313 Palm Ave]

Coquina Beach Club 103

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront

[CBC103]

Pelican Cove 12

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Bayfront

[PC12]

West Bay Point Moorings 155

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View:

[WBPM 155]

Island Beach Club 24

Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach View: Beachfront

[IBC24]

637 Norton

Bed & Bath: 4/3½ Sleeps: 8 Location: Longboat Key View: Canal

[637 Norton]

West Bay Point Moorings 42

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Bayfront

[WBPM 42]

Island Beach Club 21

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[IBC21]

Bradenton Beach Club 228

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[Bradbc228]

Harbor Lane 2 Tranquility

Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach

[HarborLane2]

Gulf Watch 205

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[GW205]

Gulf Watch 216

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[GW216]

Coquina Beach Club 202

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront

[CBC202]

West Bay Point Moorings 85

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Bayfront

[WBPM 85]

Anna Maria Island Club 14

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC14]

3011 Ave E-2

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[3011-2]

Club Bamboo South 120 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 120]

Bay View Condo H

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[BVH]

Pelican Cove 1

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[PC 1]

Coconuts 116

Bed & Bath: 1/1 Sleeps: 6 Location: Holmes Beach View: Beachfront

[Coconuts 116]

191 Pineneedle Drive

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[191PineNdle]

Shorewalk The Palms 205

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[ShoreW205]

211 83rd Street

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View:

[211 83rd St]

Harbor Lane 3 Sanctuary

Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach

[HarborLane3]

Gulf Watch 210

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[GW210]

882 Audubon

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[882-Audubon]

Sabal Palms 1AG

Bed & Bath: 1/1½ Sleeps: 4 Location: Bradenton View:

[Sabal 1AG]

Martinique 207 South

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[Mart 207]

Bay View Condo A

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Bayfront

[BVA]

Club Bamboo South 122 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 122]

408 Beachy Keen

Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria View: Near Beach

[408ALAM]

7520 3rd Ave W-Sandy Pines

Bed & Bath: 3/2 Sleeps: 8 Location: Bradenton View:

[7520 3rd Ave]

Shorewalk 104 - 4411

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton View:

[ShoreW104]

Anna Maria Island Club 31

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC31]

538 70th St

Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach View: Bayfront

[538 70th]

Bradenton Beach Club C

Bed & Bath: 3/2½ Sleeps: 6 Location: Bradenton Beach View: Beachfront

[Bradbc--C]

Anna Maria Island Club 11

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC11]

Bradenton Beach Club 247

Bed & Bath: 3/2½ Sleeps: 6 Location: Bradenton Beach View: Near Beach

[BradBC247]

Sandy Point Cove 112

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[SPC112]

Gulf Watch 111

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[GW111]

2206 Ave C

Bed & Bath: 4/2 Sleeps: 8 Location: Bradenton Beach View: Near Beach

[2206 Ave C]

Sandy Point 109

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach

[SP109]

Pelican Cove 8

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[PC 8]

Shorewalk 202-1 - 4675

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[ShoreW202-1]

Runaway Bay 248

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[RAB248]

Gulf View Townhouses 3

Bed & Bath: 2/2½ Sleeps: 4 Location: Holmes Beach View: Near Beach

[GVT3]

Island Beach Club 1

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[IBC 1]

Runaway Bay 257

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[RAB257]

Bradenton Beach Club 251

Bed & Bath: 3/2½ Sleeps: 6 Location: Bradenton Beach View: Near Beach

[BradBC251]

Anna Maria Island Club 12

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC12]

Club Bamboo South 301

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[Bamboo 301]

209 83rd unit B

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View:

[209 83rd B]

Bradenton Beach Club 222

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[Bradbc222]

Martinique 308 South

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[Mart 308]

Club Bamboo South 121 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 121]

Sandy Point 111

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach

[SP111]

Martinique 505 South

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[Mart 505]

Sunset Terrace 203

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[SST203]

Runaway Bay 174

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[RAB174]

2206 Ave B

Bed & Bath: 2/1 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[2206 Ave B]

5400 Unit 30

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Bayfront

[5400-Unit 30]

Gulf Watch 115

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[GW115]

Club Bamboo South 225 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 225]

Beach Castle Resort 6

Bed & Bath: 2/2 Sleeps: 6 Location: Longboat Key View: Beachfront

[BC-6]

Island Beach Club 22

Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach View: Beachfront

[IBC22]

Pelican Cove 11

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[PC11]

Pelican Cove 10

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Bayfront

[PC10]

Bradenton Beach Club 230

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach

[BradBC230]

Anna Maria Island Club 38

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[AMIC38]

266 S Harbor

Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View:

[266 SHarbor]

Club Bamboo South 123 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 123]

Beach View 8

Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View:

[BeachView 8]

Shorewalk 101- 4305

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:

[ShoreW101]

Runaway Bay 261

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[RAB261]

Runaway Bay 115

Bed & Bath: 1/1 Sleeps: 4 Location: Bradenton Beach View: Near Beach

[RAB115]

116 Maple Breeze

Bed & Bath: 4/2½ Sleeps: 7 Location: Anna Maria View: Near Beach

[116Maple]

Pelican Cove 13

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Bayfront

[PC13]

Pelican Cove 14

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[PC14]

Pelican Cove 5

Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach

[PC 5]

Martinique 203 North

Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront

[Mart 203]

111-Willow Casa Blanca

Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria View:

[111-WILL]

9912 Sandpiper

Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton View: Canal

[9912 SandPip]

Club Bamboo South 125 Studio

Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront

[Bamboo 125]

Bay View Condo D

Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront

[BVD]

Stay in an Anna Maria Island Rental with a Pool

These Anna Maria Island vacation rentals all have a beautiful and well-maintained pool right on the property for the swimmers in your group to use to their hearts’ content. You won’t have to visit the beach every time you want to take a swim, and some of these homes also feature hot tubs on the property. The weather is almost always pleasant on Anna Maria Island, so you’ll be able to comfortably swim throughout the year whether the pool is heated or not.

Explore Anna Maria Island

Anna Maria Island is widely known for being one of the top island destinations in the U.S. When you’re not enjoying your pool vacation rental, you can partake in snorkeling, parasailing, jet-skiing, fishing charters, wildlife tours, golfing, sunset boat tours and so much more. These homes are also situated in some of the most popular areas of the island where you can walk to dozens of fun attractions such as public beaches, restaurants, boutiques, markets, and piers. Let us help you find the perfect home with a pool on our world-famous island. Give us a call at (800) 237-2252 for more details on any of these Anna Maria Island rentals and to reserve them for your next trip!