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)

2206 Ave C

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

[2206 Ave C]

Bradenton Beach Club A

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

[Bradbc-A]

Gulf View 103

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

[GV103]

Sunplaza 115

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

[Sunplaza 115]

707 N Bay The Shell House

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

[707BAY]

Club Bamboo South 220 Studio

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

[Bamboo 220]

Bay View Condo A

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

[BVA]

Harbor Lane 3 Sanctuary

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

[HarborLane3]

Sandy Point Cove 112

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

[SPC112]

Sandy Point 109

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

[SP109]

3011 Ave E-2

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

[3011-2]

Harbor Lane 1 Serenity

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

[HarborLane1]

210-2 Haverkos

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

[210-2 Hav]

Bay View Condo D

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

[BVD]

210-1 Haverkos

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

[210-1 Hav]

Bradenton Beach Club 247

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

[BradBC247]

Bradenton Beach Club 238

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

[Bradbc238]

Anna Maria Island Club 45

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

[AMIC45]

Shorewalk 104

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

[ShoreW104]

Anna Maria Island Club 14

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

[AMIC14]

Bradenton Beach Club 251

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

[BradBC251]

Coquina Beach Club 206

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

[CBC206]

Coquina Beach Club 102

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

[CBC102]

Runaway Bay 261

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

[RAB261]

3011 Ave E-3

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

[3011-3]

Beach View 8

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

[BeachView 8]

Townhomes in the Cay

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

[THC A1]

Island Beach Club 22

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

[IBC22]

Bradenton Beach Club 222

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

[Bradbc222]

211 83rd Street

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

[211 83rd St]

Runaway Bay 187

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

[RAB187]

Martinique 308 South

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

[Mart 308]

Club Bamboo South 123 Studio

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

[Bamboo 123]

518 71st St--Palm Paradise

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

[518 71st]

Bay View Condo H

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

[BVH]

408 Beachy Keen

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

[408ALAM]

Bay View Condo C

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

[BVC]

405 Bay Palms

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

[405 Bay]

Coquina Beach Club 103

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

[CBC103]

Sunset Terrace 203

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

[SST203]

Bradenton Beach Club 249

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

[BradBC249]

Pelican Cove 14

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

[PC14]

Club Bamboo South 122 Studio

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

[Bamboo 122]

Runaway Bay 230

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

[RAB230]

Anna Maria Island Club 38

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

[AMIC38]

Pelican Cove 5

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

[PC5]

Anna Maria Island Club 12

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

[AMIC12]

7717 27th Ave W-Chili Cove

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

[7717 27th]

Gulf Watch 210

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

[GW210]

Bradenton Beach Club 230

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

[BradBC230]

Sandy Point Cove 114

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

[SPC114]

Pelican Cove 4

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

[PC4]

Pelican Cove 10

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

[PC10]

Coquina Moorings 201

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

[CM-201]

637 Norton

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

[637 Norton]

La Playita Condo 2

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

[LAPLAY2]

Coquina Reef 15

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

[CR15]

Club Bamboo South 225 Studio

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

[Bamboo 225]

West Bay Point Moorings 155

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

[WBPM 155]

Sunbow Bay 212

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

[SBB212]

313 Island Walk

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

[313 64th]

Harbor Lane 2 Tranquility

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

[HarborLane2]

Bradenton Beach Club 228

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

[Bradbc228]

Gulf Watch 211

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

[GW211]

Island Beach Club 1

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

[IBC1]

Gulf Watch 111

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

[GW111]

Gulf View Townhouses 3

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

[GVT3]

Gulf Watch 104

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

[GW104]

7520 3rd Ave-Sandy Pines

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

[7520 3rd Ave]

Shorewalk 101

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

[ShoreW101]

Pelican Cove 12

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

[PC12]

Sabal Palms 1AG

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

[Sabal 1AG]

Fountain Head 6

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

[FH6]

Club Bamboo South 301

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

[Bamboo 301]

Pelican Cove 1

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

[PC1]

Pelican Cove 9

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

[PC9]

Gulf Watch 216

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

[GW216]

Club Bamboo South 121 Studio

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

[Bamboo 121]

Pelican Cove 11

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

[PC11]

Martinique 207 South

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

[Mart 207]

Shorewalk The Palms 205

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

[ShoreW205]

LaPlayita Condo 5

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

[LAPLAY5]

Pelican Cove 8

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

[PC8]

Sandy Point 111

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

[SP111]

Martinique 306 South

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

[Mart306]

811Audubon

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

[811Audubon]

Meadow Croft 5714

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

[Meadow 5714]

Pelican Cove 13

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

[PC13]

Island Beach Club 24

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

[IBC24]

Cayman 104

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

[Cayman 104]

609 Concord Lane

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

[609 Concord]

Sandy Point 204

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

[SP204]

Runaway Bay 205

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

[RAB205]

Gulf Watch 205

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

[GW205]

Pelican Cove 2

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

[PC2]

Runaway Bay 115

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

[RAB115]

3011 Ave E-1

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

[3011-1]

Anna Maria Island Club 31

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

[AMIC31]

Fountain Head 8

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

[FH8]

Gulf Watch 115

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

[GW115]

Beach Castle Resort 6

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

[BC-6]

146 Wild Palm

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

[146 Wild]

Island Beach Club 3

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

[IBC3]

Anna Maria Island Club 26

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

[AMIC26]

Island Beach Club 21

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

[IBC21]

538 70th St

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

[538 70th]

West Bay Point Moorings 42

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

[WBPM 42]

Runaway Bay 174

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

[RAB 174]

Shorewalk 202-1

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

[ShoreW202-1]

882 Audubon

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

[882-Audubon]

Runaway Bay 248

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

[RAB248]

Harbor Lane 4 Harmony

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

[HarborLane4]

Martinique 203 North

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

[Mart 203]

Club Bamboo South 125 Studio

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

[Bamboo 125]

Coquina Beach Club 202

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

[CBC202]

217 84th Street

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

[217 84TH]

Club Bamboo South 119 Studio

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

[Bamboo 119]

510 Bayview

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

[510Bayview]

Martinique 505 South

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

[Mart 505]

Sandy Point Cove 106

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

[SPC106]

517 Key Royale

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

[517 Key]

Sandy Point 205

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

[SP205]

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!