Anna Maria Island Pool Vacation Rentals
Enjoy your own private pool on vacation
Homes and condos with swimming pools and some with hot tubs. 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 pool vacation rentals. 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.
Beautiful, well maintained pools for those who love swimming
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!
My Rentals (882 Audubon
From $107/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton
View: Near Beach
[882Audubon]
Sunbow Bay 108
From $127/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Bayfront
[Sbb108]
Bay View Condo H
From $207/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[BVH]
Runaway Bay 185
From $114/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[RAB 185]
Island Beach Club 22
From $171/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC22]
Coquina Reef 15
From $114/night
Bed & Bath: 1/1
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[CR15]
146 Wild Palm
From $53/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton
View: Near Beach
[146 Wild]
Bradenton Beach Club 226
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc226]
Mart 306
From $117/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Beachfront
[Mart306]
Pelican Roost 505
From $464/night
Bed & Bath: 5/5
Sleeps: 10
Location: Anna Maria
View: Canal
[505 South Ba]
Island Walk 313
From $200/night
Bed & Bath: 3/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[313 64th]
Harbor Lane 2 Tranquility
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane2]
Harbor Lane 3 Sanctuary
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane3]
Club Bamboo South 225 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 225]
Runaway Bay 115
From $96/night
Bed & Bath: 1/1
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB115]
Harbor Lane 1 Serenity
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane1]
Coquina Beach Club 202
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC202]
Fountain Head 8
From $135/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[FH8]
604 Ambassador Lane
From $225/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View:
[604 Ambassa]
510 Bayview
From $500/night
Bed & Bath: 5/5
Sleeps: 10
Location: Holmes Beach
View: Canal
[510Bayview]
Island Beach Club 1
From $214/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC1]
614 Concord Lane
From $171/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Canal
[614CONCORD]
Island Beach Club 24
From $186/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC24]
707 N Bay The Shell House
From $275/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Anna Maria
View:
[707BAY]
Island Beach Club 4
From $129/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC4]
637 Norton
From $543/night
Bed & Bath: 4/3½
Sleeps: 8
Location: Longboat Key
View: Canal
[637 Norton]
Harbor Lane 4 Harmony
From $144/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[HarborLane4]
Sandy Point Cove 114
From $121/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[SPC114]
Club Bamboo South 224 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 224]
Anna Maria Island Club 46
From $257/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC46]
Anna Maria Island Club 45
From $307/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC45]
West Bay Cove 222
From $129/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[WBC 600]
538 70th St
From $188/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[538 70th]
Townhomes in the Cay
From $121/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton
View: Near Beach
[THC A1]
Bay Watch 7B
From $93/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bw7b]
Club Bamboo South 220 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 220]
Bay View Condo C
From $186/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[BVC]
Bradenton Beach Club 247
From $214/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC247]
Martinique 505 South
From $157/night
Bed & Bath: 2/2
Sleeps: 5
Location: Holmes Beach
View: Beachfront
[Mart 505]
Coquina Moorings 202
From $214/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[CM-202]
LaPlayita Condo
From $114/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[LAPLAY5]
Pelican Cove 2
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC2]
Gulf Watch 205
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW205]
Runaway Bay 257
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB257]
Bridgeport 112
From $164/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[BP112]
541 67th Street
From $400/night
Bed & Bath: 5/4
Sleeps: 10
Location: Holmes Beach
View: Canal
[541 67TH]
Pelican Cove 12
From $200/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC12]
West Bay Point Moorings 101
From $183/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Bayfront
[WBPM 101]
Pelican Cove 8
From $200/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[PC8]
Sandy Point 111
From $135/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[SP111]
518 71st St--Palm Paradise
From $233/night
Bed & Bath: 3/2
Sleeps: 6
Location: Holmes Beach
View: Canal
[518 71st]
Coquina Moorings 201
From $214/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[CM-201]
Pelican Cove 6
From $200/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[PC6]
Pelican Cove 4
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC4]
Club Bamboo South 217 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 217]
Club Bamboo South 121 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 121]
Island Beach Club 21
From $143/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC21]
Pelican Cove 13
From $200/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Bayfront
[PC13]
Runaway Bay 174
From $129/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[RAB 174]
Gulf Watch 111
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW111]
Runaway Bay 261
From $114/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB261]
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]
West Bay Point Moorings 193
From $117/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[WBPM193]
Coquina Beach Club 206
From $221/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[CBC206]
Club Bamboo South 120 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 120]
Runaway Bay 205
From $129/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[RAB205]
Island Village
From $85/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[IV215]
Club Bamboo South 123 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 123]
Runaway Bay 230
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB230]
Club Bamboo South 122 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 122]
Sandy Point Cove 112
From $135/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[SPC112]
Bradenton Beach Club 248
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc248]
Sunplaza 115
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[Sunplaza 115]
Club Bamboo South 218 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 218]
Sunbow Bay A1
From $113/night
Bed & Bath: 3/3
Sleeps: 8
Location: Holmes Beach
View: Near Beach
[SbbA1]
Anna Maria Island Club 38
From $257/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC38]
WestChester LBK
From $150/night
Bed & Bath: 2/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[WestChester]
Anna Maria Island Club 26
From $257/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC26]
Coquina Beach Club 102
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC102]
Mart 207
From $229/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[Mart 207]
Martinique 504 South
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Holmes Beach
View: Beachfront
[Mart 504]
529 Key Royale Drive
From $521/night
Bed & Bath: 6/5
Sleeps: 12
Location: Holmes Beach
View: Canal
[529 Key]
3011 Ave E-3
From $140/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[3011-3]
RunAway Bay 274
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB274]
2307 Ave C Unit A
From $189/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[2307 Ave C]
Villas-206
From $264/night
Bed & Bath: 3/3½
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[Villas-206]
Sandy Point 106
From $135/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[SP106]
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 3
From $200/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[PC3]
Club Bamboo South 301
From $143/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[Bamboo 301]
Club Bamboo South 119 Studio
From $125/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 119]
Gulf Watch 216
From $150/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[GW216]
Martinique 603 South
From $286/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[Mart 603]
Club Bamboo South 219 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 219]
Gulf Watch 210
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW210]
Fountain Head 6
From $135/night
Bed & Bath: 2/1½
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[FH6]
Bradenton Beach Club 252
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc252]
Pelican Cove 5
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC5]
244 South Harbor
From $150/night
Bed & Bath: 2/3
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[244 SHarbor]
Gulf Watch 104
From $136/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[GW104]
Club Bamboo South 124 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 124]
Runaway Bay 164
From $96/night
Bed & Bath: 1/1
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB164]
Sandy Point 205
From $135/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[SP205]
Sunset Terrace 203
From $186/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[SST203]
1209 Spoonbill Landings Circle
From $167/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton
View: Bayfront
[1209 Spoon]
Bay View Condo E
From $171/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Bayfront
[BVE]
Pelican Cove 14
From $200/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC14]
Coquina Beach Club 103
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC103]
Gulf Watch 115
From $150/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[GW115]
Club Bamboo South 125 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 125]
Shorewalk The Palms 205
From $120/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton
View:
[ShoreW205]
Gulf View Townhouses 3
From $129/night
Bed & Bath: 2/2½
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[GVT3]
West Bay Point Moorings 155
From $110/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[WBPM 155]
Pelican Cove 10
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Bayfront
[PC10]
Gulf Watch 211
From $136/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[GW211]
Anna Maria Island Club 12
From $221/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC12]
Island Beach Club 3
From $143/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC3]
Beach Castle Resort 6
From $270/night
Bed & Bath: 2/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[BC6]
West Bay Point Moorings 42
From $150/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[WBPM 42]
Bradenton Beach Club 238
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc238]
Pelican Cove 9
From $200/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Bayfront
[PC9]
Bradenton Beach Club 228
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc228]
Bradenton Beach Club 249
From $214/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC249]
Anna Maria Island Club 31
From $257/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC31]
Whitney Beach 145
From $83/night
Bed & Bath: 2/2
Sleeps: 4
Location: Longboat Key
View: Near Beach
[WB145]
517 Key Royale
From $486/night
Bed & Bath: 5/5
Sleeps: 10
Location: Holmes Beach
View: Canal
[517 Key]
Pelican Cove 11
From $200/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC11]
Bradenton Beach Club A
From $314/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[Bradbc-A]
Bradenton Beach Club 251
From $214/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC251]
Runaway Bay 248
From $129/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[RAB248]
617 Dundee Lane
From $357/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Canal
[617 Dundee]
