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. Nothing compares with swimming in your own backyard. 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)

Anna Maria Island Club 31

From $243/night

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

[AMIC31]

Bradenton Beach Club 230

From $186/night

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

[BradBC230]

3011 Ave E-1

From $200/night

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

[3011-1]

Pelican Cove 8

From $225/night

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

[PC8]

Meadow Croft 5714

From $117/night

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

[Meadow 5714]

Island Beach Club 3

From $171/night

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

[IBC3]

Pelican Cove 5

From $225/night

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

[PC5]

Shorewalk The Palms 205

From $100/night

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

[ShoreW205]

Harbor Lane 4 Harmony

From $150/night

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

[HarborLane4]

Gulf Watch 115

From $150/night

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

[GW115]

Sunbow Bay 108

From $133/night

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

[Sbb108]

North Beach Village 63

From $143/night

Bed & Bath: 2/2½ Sleeps: 6 Location: Holmes Beach View: Near Beach

[NBV-63]

609 Concord Lane

From $286/night

Bed & Bath: 3/2 Sleeps: 5 Location: Holmes Beach View: Canal

[609 Concord]

Harbor Lane 2 Tranquility

From $120/night

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

[HarborLane2]

Beachy Keen 408

From $275/night

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

[408ALAM]

Sunbow Bay A1

From $193/night

Bed & Bath: 3/3 Sleeps: 8 Location: Holmes Beach View: Near Beach

[SbbA1]

Gulf Watch 205

From $136/night

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

[GW205]

Coquina Beach Club 206

From $221/night

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

[CBC206]

Sandy Point 205

From $100/night

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

[SP205]

Sandy Point 111

From $121/night

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

[SP111]

Island Village

From $85/night

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

[IV215]

811Audubon

From $117/night

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

[811Audubon]

405 Bay Palms

From $193/night

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

[405 Bay]

3011 Ave E-3

From $140/night

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

[3011-3]

Island Beach Club 1

From $186/night

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

[IBC1]

510 Bayview

From $529/night

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

[510Bayview]

518 71st St--Palm Paradise

From $257/night

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

[518 71st]

Townhomes in the Cay

From $121/night

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

[THC A1]

Gulf View 103

From $221/night

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

[GV103]

7717 27th Ave W-Chili Cove

From $250/night

Bed & Bath: 4/2½ Sleeps: 10 Location: Bradenton View:

[7717 27th]

210-1 Haverkos

From $114/night

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

[210-1 Hav]

Club Bamboo South 220 Studio

From $155/night

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

[Bamboo 220]

Club Bamboo South 120 Studio

From $155/night

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

[Bamboo 120]

Sunset Terrace 203

From $186/night

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

[SST203]

Fountain Head 8

From $135/night

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

[FH8]

1405 63rd St West

From $136/night

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

[1405 63rd W]

Club Bamboo South 119 Studio

From $155/night

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

[Bamboo 119]

Runaway Bay 248

From $129/night

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

[RAB248]

Sandy Point 204

From $121/night

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

[SP204]

Pelican Cove 11

From $175/night

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

[PC11]

Island Beach Club 21

From $171/night

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

[IBC21]

Runaway Bay 261

From $114/night

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

[RAB261]

210 House on Haverkos

From $243/night

Bed & Bath: 3/2½ Sleeps: 8 Location: Holmes Beach View:

[210 House]

WestChester LBK 304A

From $150/night

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

[WestChester]

Runaway Bay 187

From $131/night

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

[RAB187]

Pelican Cove 2

From $225/night

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

[PC2]

882 Audubon

From $107/night

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

[882Audubon]

Sandy Point Cove 114

From $129/night

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

[SPC114]

Club Bamboo South 224 Studio

From $155/night

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

[Bamboo 224]

Bradenton Beach Club 247

From $214/night

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

[BradBC247]

Runaway Bay 115

From $96/night

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

[RAB115]

538 70th St

From $188/night

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

[538 70th]

Cayman 108

From $143/night

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

[Cayman 108]

Anna Maria Island Club 45

From $307/night

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

[AMIC45]

Runaway Bay 230

From $143/night

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

[RAB230]

517 Key Royale

From $1000/night

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

[517 Key]

721 Estuary

From $103/night

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

[721EST]

637 Norton

From $543/night

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

[637 Norton]

217 84th Street

From $186/night

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

[217 84TH]

Shorewalk 101

From $100/night

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

[ShoreW101]

2307 Ave C Unit A

From $189/night

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

[2307 Ave C]

Sandy Point 109

From $100/night

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

[SP109]

Pelican Cove 12

From $225/night

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

[PC12]

707 N Bay The Shell House

From $275/night

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

[707BAY]

313 Island Walk

From $157/night

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

[313 64th]

Coquina Reef 15

From $114/night

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

[CR15]

Pelican Cove 3

From $225/night

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

[PC3]

Bay View Condo A

From $200/night

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

[BVA]

Harbor Lane 1 Serenity

From $120/night

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

[HarborLane1]

Pelican Cove 13

From $225/night

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

[PC13]

Coquina Moorings 201

From $186/night

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

[CM-201]

Martinique 207 South

From $123/night

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

[Mart 207]

Bradenton Beach Club A

From $360/night

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

[Bradbc-A]

Martinique 306 South

From $171/night

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

[Mart306]

Whitney Beach 145

From $83/night

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

[WB145]

Anna Maria Island Club 26

From $257/night

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

[AMIC26]

Martinique 203 North

From $129/night

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

[Mart 203]

Coquina Beach Club 202

From $221/night

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

[CBC202]

Bradenton Beach Club 238

From $143/night

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

[Bradbc238]

210-2 Haverkos

From $148/night

Bed & Bath: 2/1½ Sleeps: 4 Location: Holmes Beach View:

[210-2 Hav]

Shorewalk 202-1

From $100/night

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

[ShoreW202-1]

Bradenton Beach Club 228

From $186/night

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

[Bradbc228]

Island Beach Club 24

From $171/night

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

[IBC24]

Sabal Palms 1AG

From $55/night

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

[Sabal 1AG]

Sunbow Bay 212

From $143/night

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

[SBB212]

7520 3rd Ave-Sandy Pines

From $136/night

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

[7520 3rd Ave]

Club Bamboo South 301

From $143/night

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

[Bamboo 301]

West Bay Point Moorings 193

From $117/night

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

[WBPM193]

Martinique 505 South

From $129/night

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

[Mart 505]

West Bay Point Moorings 155

From $110/night

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

[WBPM 155]

Club Bamboo South 123 Studio

From $155/night

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

[Bamboo 123]

Coquina Beach Club 103

From $221/night

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

[CBC103]

Coquina Beach Club 102

From $221/night

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

[CBC102]

3011 Ave E-2

From $165/night

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

[3011-2]

Bradenton Beach Club 249

From $214/night

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

[BradBC249]

Bradenton Beach Club 251

From $214/night

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

[BradBC251]

Gulf View Townhouses 3

From $150/night

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

[GVT3]

620 Gladstone

From $386/night

Bed & Bath: 4/3 Sleeps: 7 Location: Holmes Beach View: Canal

[620 Gladston]

Bay View Condo C

From $157/night

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

[BVC]

Bay View Condo D

From $157/night

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

[BVD]

Club Bamboo South 122 Studio

From $155/night

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

[Bamboo 122]

Anna Maria Island Club 12

From $200/night

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

[AMIC12]

Sunplaza 115

From $392/night

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

[Sunplaza 115]

Gulf Watch 104

From $136/night

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

[GW104]

Cayman 104

From $143/night

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

[Cayman 104]

Gulf Watch 216

From $150/night

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

[GW216]

146 Wild Palm

From $53/night

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

[146 Wild]

Sandy Point Cove 112

From $114/night

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

[SPC112]

516 70th St

From $411/night

Bed & Bath: 4/4 Sleeps: 9 Location: Holmes Beach View: Canal

[516 70th St]

West Bay Point Moorings 42

From $150/night

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

[WBPM 42]

Pelican Cove 14

From $225/night

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

[PC14]

Beach View 8

From $150/night

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

[BeachView 8]

Pelican Cove 4

From $225/night

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

[PC4]

2206 Ave C

From $357/night

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

[2206 Ave C]

Gulf Watch 211

From $136/night

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

[GW211]

Seascape Unit 103

From $214/night

Bed & Bath: 3/2 Sleeps: 6 Location: Longboat Key View: Beachfront

[SEASCAPE103]

Harbor Lane 3 Sanctuary

From $120/night

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

[HarborLane3]

Runaway Bay 257

From $129/night

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

[RAB257]

Gulf Watch 111

From $136/night

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

[GW111]

Fountain Head 6

From $135/night

Bed & Bath: 2/1½ Sleeps: 4 Location: Holmes Beach View: Near Beach

[FH6]

La Playita Condo 2

From $114/night

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

[LAPLAY2]

Shorewalk 104

From $100/night

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

[ShoreW104]

Pelican Cove 1

From $225/night

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

[PC1]

Runaway Bay 174

From $129/night

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

[RAB 174]

Bay View Condo H

From $186/night

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

[BVH]

617 Dundee Lane

From $357/night

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

[617 Dundee]

Gulf Watch 210

From $136/night

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

[GW210]

Bradenton Beach Club 252

From $186/night

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

[Bradbc252]

Club Bamboo South 125 Studio

From $155/night

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

[Bamboo 125]

10316Spoonbill-Casa in the Cay

From $299/night

Bed & Bath: 4/3 Sleeps: 8 Location: Bradenton View:

[10316 Spoon]

Runaway Bay 205

From $129/night

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

[RAB205]

LaPlayita Condo 5

From $114/night

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

[LAPLAY5]

Martinique 308 South

From $129/night

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

[Mart 308]

Club Bamboo South 121 Studio

From $155/night

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

[Bamboo 121]

Club Bamboo South 225 Studio

From $155/night

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

[Bamboo 225]

Pelican Cove 9

From $225/night

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

[PC9]

611 Gladstone

From $386/night

Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach View:

[611 Gladston]

211 83rd Street

From $257/night

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

[211 83rd St]

Bradenton Beach Club 248

From $186/night

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

[Bradbc248]

Pelican Cove 10

From $225/night

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

[PC10]

Enjoy your own private pool on vacation

These 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.

Enjoy living in luxury in one of the best vacation destinations in the U.S.

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 options and to reserve them for your next trip!