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)

Gulf Watch 211

From $136/night

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

[GW211]

Beachy Keen 408

From $275/night

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

[408ALAM]

Anna Maria Island Club 26

From $257/night

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

[AMIC26]

Bradenton Beach Club 252

From $186/night

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

[Bradbc252]

Pelican Cove 1

From $225/night

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

[PC1]

609 Concord Lane

From $286/night

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

[609 Concord]

Club Bamboo South 301

From $143/night

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

[Bamboo 301]

Harbor Lane 4 Harmony

From $150/night

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

[HarborLane4]

611 Gladstone

From $386/night

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

[611 Gladston]

Gulf Watch 115

From $150/night

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

[GW115]

Shorewalk The Palms 205

From $100/night

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

[ShoreW205]

Shorewalk 101

From $100/night

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

[ShoreW101]

811Audubon

From $117/night

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

[811Audubon]

Sandy Point Cove 112

From $114/night

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

[SPC112]

Beach View 8

From $150/night

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

[BeachView 8]

Bradenton Beach Club A

From $357/night

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

[Bradbc-A]

Sunplaza 115

From $360/night

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

[Sunplaza 115]

Club Bamboo South 225 Studio

From $155/night

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

[Bamboo 225]

Pelican Cove 13

From $225/night

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

[PC13]

Pelican Cove 5

From $200/night

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

[PC5]

LaPlayita Condo 5

From $114/night

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

[LAPLAY5]

Club Bamboo South 119 Studio

From $155/night

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

[Bamboo 119]

7520 3rd Ave-Sandy Pines

From $136/night

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

[7520 3rd Ave]

Cayman 108

From $143/night

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

[Cayman 108]

882 Audubon

From $107/night

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

[882Audubon]

Cayman 104

From $143/night

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

[Cayman 104]

Club Bamboo South 123 Studio

From $155/night

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

[Bamboo 123]

210 House on Haverkos

From $243/night

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

[210 House]

Meadow Croft 5714

From $117/night

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

[Meadow 5714]

Bay View Condo C

From $157/night

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

[BVC]

Coquina Beach Club 102

From $221/night

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

[CBC102]

617 Dundee Lane

From $357/night

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

[617 Dundee]

Martinique 207 South

From $123/night

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

[Mart 207]

Sandy Point 109

From $100/night

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

[SP109]

405 Bay Palms

From $193/night

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

[405 Bay]

North Beach Village 63

From $143/night

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

[NBV-63]

Pelican Cove 10

From $225/night

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

[PC10]

Harbor Lane 1 Serenity

From $120/night

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

[HarborLane1]

Bradenton Beach Club 222

From $129/night

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

[Bradbc222]

Sunset Terrace 203

From $186/night

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

[SST203]

620 Gladstone

From $386/night

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

[620 Gladston]

Townhomes in the Cay

From $121/night

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

[THC A1]

Gulf Watch 205

From $136/night

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

[GW205]

Shorewalk 202-1

From $100/night

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

[ShoreW202-1]

Bay View Condo H

From $186/night

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

[BVH]

Sandy Point 111

From $121/night

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

[SP111]

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]

Bradenton Beach Club 230

From $186/night

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

[BradBC230]

707 N Bay The Shell House

From $275/night

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

[707BAY]

West Bay Point Moorings 193

From $117/night

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

[WBPM193]

3011 Ave E-2

From $165/night

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

[3011-2]

Runaway Bay 187

From $131/night

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

[RAB187]

637 Norton

From $543/night

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

[637 Norton]

Gulf Watch 216

From $150/night

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

[GW216]

Pelican Cove 3

From $175/night

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

[PC3]

2206 Ave C

From $357/night

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

[2206 Ave C]

146 Wild Palm

From $53/night

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

[146 Wild]

Anna Maria Island Club 31

From $243/night

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

[AMIC31]

Island Beach Club 21

From $171/night

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

[IBC21]

518 71st St--Palm Paradise

From $257/night

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

[518 71st]

Gulf Watch 104

From $136/night

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

[GW104]

Bradenton Beach Club 228

From $186/night

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

[Bradbc228]

West Bay Point Moorings 42

From $150/night

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

[WBPM 42]

Sandy Point Cove 106

From $121/night

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

[SPC106]

210-1 Haverkos

From $114/night

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

[210-1 Hav]

Gulf Watch 111

From $136/night

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

[GW111]

Pelican Cove 9

From $225/night

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

[PC9]

Martinique 505 South

From $129/night

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

[Mart 505]

217 84th Street

From $186/night

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

[217 84TH]

Coquina Moorings 201

From $186/night

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

[CM-201]

Sabal Palms 1AG

From $55/night

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

[Sabal 1AG]

Bradenton Beach Club 247

From $214/night

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

[BradBC247]

510 Bayview

From $529/night

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

[510Bayview]

Harbor Lane 2 Tranquility

From $120/night

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

[HarborLane2]

Sunbow Bay A1

From $193/night

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

[SbbA1]

Pelican Cove 4

From $225/night

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

[PC4]

Runaway Bay 261

From $114/night

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

[RAB261]

Coquina Reef 15

From $114/night

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

[CR15]

Pelican Cove 2

From $225/night

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

[PC2]

538 70th St

From $188/night

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

[538 70th]

Bradenton Beach Club 248

From $186/night

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

[Bradbc248]

517 Key Royale

From $1000/night

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

[517 Key]

210-2 Haverkos

From $148/night

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

[210-2 Hav]

Coquina Beach Club 206

From $221/night

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

[CBC206]

Island Beach Club 3

From $171/night

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

[IBC3]

Fountain Head 6

From $135/night

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

[FH6]

3011 Ave E-3

From $140/night

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

[3011-3]

Fountain Head 8

From $135/night

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

[FH8]

Runaway Bay 205

From $129/night

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

[RAB205]

313 Island Walk

From $157/night

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

[313 64th]

Sandy Point 205

From $107/night

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

[SP205]

Bradenton Beach Club 238

From $143/night

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

[Bradbc238]

Bay View Condo A

From $200/night

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

[BVA]

Runaway Bay 248

From $129/night

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

[RAB248]

West Bay Point Moorings 155

From $110/night

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

[WBPM 155]

Island Beach Club 24

From $171/night

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

[IBC24]

211 83rd Street

From $257/night

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

[211 83rd St]

Bay View Condo D

From $157/night

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

[BVD]

721 Estuary

From $103/night

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

[721EST]

Coquina Beach Club 202

From $221/night

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

[CBC202]

Pelican Cove 11

From $175/night

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

[PC11]

Harbor Lane 3 Sanctuary

From $120/night

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

[HarborLane3]

Pelican Cove 14

From $225/night

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

[PC14]

Martinique 203 North

From $129/night

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

[Mart 203]

Anna Maria Island Club 45

From $286/night

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

[AMIC45]

Sandy Point 204

From $121/night

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

[SP204]

Pelican Cove 8

From $225/night

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

[PC8]

Shorewalk 104

From $100/night

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

[ShoreW104]

516 70th St

From $375/night

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

[516 70th St]

Anna Maria Island Club 12

From $200/night

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

[AMIC12]

Club Bamboo South 120 Studio

From $155/night

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

[Bamboo 120]

Bradenton Beach Club 251

From $214/night

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

[BradBC251]

Martinique 306 South

From $171/night

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

[Mart306]

Club Bamboo South 122 Studio

From $155/night

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

[Bamboo 122]

7717 27th Ave W-Chili Cove

From $250/night

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

[7717 27th]

Coquina Beach Club 103

From $221/night

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

[CBC103]

Club Bamboo South 125 Studio

From $155/night

Bed & Bath: Studio/1 Sleeps: 5 Location: Bradenton Beach View: Beachfront

[Bamboo 125]

Sunbow Bay 212

From $143/night

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

[SBB212]

Gulf View Townhouses 3

From $150/night

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

[GVT3]

Sandy Point Cove 114

From $129/night

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

[SPC114]

Bradenton Beach Club 249

From $214/night

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

[BradBC249]

Runaway Bay 230

From $143/night

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

[RAB230]

3011 Ave E-1

From $200/night

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

[3011-1]

Runaway Bay 115

From $96/night

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

[RAB115]

Island Beach Club 22

From $171/night

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

[IBC22]

Island Beach Club 1

From $186/night

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

[IBC1]

Club Bamboo South 220 Studio

From $155/night

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

[Bamboo 220]

Pelican Cove 12

From $225/night

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

[PC12]

La Playita Condo 2

From $114/night

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

[LAPLAY2]

Gulf View 103

From $221/night

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

[GV103]

1405 63rd St West

From $136/night

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

[1405 63rd W]

Gulf Watch 210

From $136/night

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

[GW210]

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!