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 View 103

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

[GV103]

Anna Maria Island Club 14

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

[AMIC14]

Bradenton Beach Club 222

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

[Bradbc222]

Sandy Point 109

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

[SP109]

Meadow Croft 5714

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

[Meadow 5714]

Gulf Watch 104

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

[GW104]

Harbor Lane 2 Tranquility

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

[HarborLane2]

Island Beach Club 22

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

[IBC22]

Shorewalk The Palms 205

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

[ShoreW205]

Club Bamboo South 121 Studio

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

[Bamboo 121]

Island Beach Club 3

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

[IBC3]

Sabal Palms 1AG

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

[Sabal 1AG]

Bradenton Beach Club 228

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

[Bradbc228]

Shorewalk 202-1

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

[ShoreW202-1]

Pelican Cove 9

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

[PC9]

Bay View Condo C

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

[BVC]

Shorewalk 104

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

[ShoreW104]

Gulf Watch 210

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

[GW210]

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]

Martinique 203 North

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

[Mart 203]

Island Beach Club 1

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

[IBC1]

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]

Pelican Cove 1

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

[PC1]

Harbor Lane 3 Sanctuary

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

[HarborLane3]

LaPlayita Condo 5

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

[LAPLAY5]

Club Bamboo South 225 Studio

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

[Bamboo 225]

707 N Bay The Shell House

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

[707BAY]

2206 Ave C

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

[2206 Ave C]

Anna Maria Island Club 26

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

[AMIC26]

Runaway Bay 115

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

[RAB115]

637 Norton

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

[637 Norton]

Club Bamboo South 123 Studio

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

[Bamboo 123]

Gulf Watch 211

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

[GW211]

3011 Ave E-2

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

[3011-2]

Club Bamboo South 301

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

[Bamboo 301]

3011 Ave E-3

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

[3011-3]

Coquina Beach Club 202

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

[CBC202]

Cayman 104

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

[Cayman 104]

Martinique 207 South

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

[Mart 207]

211 83rd Street

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

[211 83rd St]

Beach View 8

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

[BeachView 8]

Bradenton Beach Club 249

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

[BradBC249]

Pelican Cove 10

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

[PC10]

Townhomes in the Cay

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

[THC A1]

Bradenton Beach Club 251

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

[BradBC251]

Gulf View Townhouses 3

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

[GVT3]

Gulf Watch 216

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

[GW216]

Sandy Point Cove 106

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

[SPC106]

217 84th Street

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

[217 84TH]

313 Island Walk

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

[313 64th]

408 Beachy Keen

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

[408ALAM]

West Bay Point Moorings 155

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

[WBPM 155]

Runaway Bay 230

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

[RAB230]

Sunset Terrace 203

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

[SST203]

Sandy Point Cove 112

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

[SPC112]

7717 27th Ave W-Chili Cove

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

[7717 27th]

Island Beach Club 24

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

[IBC24]

Gulf Watch 111

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

[GW111]

Sunbow Bay 212

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

[SBB212]

Runaway Bay 205

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

[RAB205]

Gulf Watch 115

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

[GW115]

Martinique 306 South

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

[Mart306]

Fountain Head 6

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

[FH6]

La Playita Condo 2

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

[LAPLAY2]

Pelican Cove 8

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

[PC8]

West Bay Point Moorings 42

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

[WBPM 42]

Martinique 505 South

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

[Mart 505]

Club Bamboo South 122 Studio

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

[Bamboo 122]

Shorewalk 101

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

[ShoreW101]

Fountain Head 8

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

[FH8]

Bay View Condo H

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

[BVH]

3011 Ave E-1

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

[3011-1]

Club Bamboo South 119 Studio

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

[Bamboo 119]

538 70th St

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

[538 70th]

517 Key Royale

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

[517 Key]

Bay View Condo A

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

[BVA]

Club Bamboo South 125 Studio

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

[Bamboo 125]

Bradenton Beach Club 230

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

[BradBC230]

Bradenton Beach Club A

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

[Bradbc-A]

Pelican Cove 13

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

[PC13]

Anna Maria Island Club 31

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

[AMIC31]

Pelican Cove 14

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

[PC14]

811Audubon

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

[811Audubon]

Sandy Point 205

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

[SP205]

510 Bayview

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

[510Bayview]

Sandy Point 204

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

[SP204]

Harbor Lane 1 Serenity

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

[HarborLane1]

Coquina Beach Club 102

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

[CBC102]

Pelican Cove 4

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

[PC4]

Pelican Cove 2

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

[PC2]

Harbor Lane 4 Harmony

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

[HarborLane4]

882 Audubon

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

[882-Audubon]

Sandy Point Cove 114

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

[SPC114]

Club Bamboo South 220 Studio

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

[Bamboo 220]

Bradenton Beach Club 247

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

[BradBC247]

Pelican Cove 11

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

[PC11]

Island Beach Club 21

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

[IBC21]

Coquina Beach Club 206

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

[CBC206]

Pelican Cove 12

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

[PC12]

Coquina Reef 15

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

[CR15]

Anna Maria Island Club 38

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

[AMIC38]

Anna Maria Island Club 12

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

[AMIC12]

7520 3rd Ave-Sandy Pines

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

[7520 3rd Ave]

Bay View Condo D

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

[BVD]

Runaway Bay 261

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

[RAB261]

Sandy Point 111

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

[SP111]

Martinique 308 South

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

[Mart 308]

Gulf Watch 205

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

[GW205]

Coquina Beach Club 103

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

[CBC103]

North Beach Village 63

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

[NBV-63]

Pelican Cove 5

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

[PC5]

Runaway Bay 248

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

[RAB248]

Beach Castle Resort 6

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

[BC-6]

405 Bay Palms

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

[405 Bay]

146 Wild Palm

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

[146 Wild]

Runaway Bay 174

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

[RAB 174]

Enjoy your own private pool on vacation

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.

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 Anna Maria Island rentals and to reserve them for your next trip!