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 (516 77th St
From $270/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Canal
[516 77th St]
Club Bamboo South 125 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 125]
Club Bamboo South 224 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 224]
Bradenton Beach Club 238
From $171/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc238]
Gulf Watch 115
From $150/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[GW115]
Sunset Terrace 203
From $186/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[SST203]
Anna Maria Island Club 26
From $257/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC26]
Pelican Cove 13
From $225/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Bayfront
[PC13]
Sandy Point 111
From $114/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[SP111]
Harbor Lane 1 Serenity
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane1]
Shorewalk The Palms 205
From $92/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton
View:
[ShoreW205]
313 Island Walk
From $200/night
Bed & Bath: 3/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[313 64th]
538 70th St
From $188/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[538 70th]
Bradenton Beach Club A
From $357/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[Bradbc-A]
Club Bamboo South 122 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 122]
Runaway Bay 257
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB257]
Pelican Cove 4
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC4]
Bradenton Beach Club 247
From $214/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC247]
Club Bamboo South 123 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 123]
Runaway Bay 205
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB205]
Bradenton Beach Club 228
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc228]
Beachy Keen 408
From $275/night
Bed & Bath: 3/2
Sleeps: 6
Location: Anna Maria
View: Near Beach
[408ALAM]
2307 Ave C Unit A
From $189/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[2307 Ave C]
3011 Ave E-2
From $165/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[3011-2]
Whitney Beach 145
From $83/night
Bed & Bath: 2/2
Sleeps: 4
Location: Longboat Key
View: Near Beach
[WB145]
637 Norton
From $543/night
Bed & Bath: 4/3½
Sleeps: 8
Location: Longboat Key
View: Canal
[637 Norton]
Pelican Cove 12
From $225/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC12]
517 Key Royale
From $486/night
Bed & Bath: 5/5
Sleeps: 10
Location: Holmes Beach
View: Canal
[517 Key]
Beach Castle Resort 6
From $270/night
Bed & Bath: 2/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[BC6]
Sandy Point 109
From $100/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[SP109]
6709-Happily Ever After
From $121/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton
View:
[6709 20th Av]
Runaway Bay 187
From $131/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Bayfront
[RAB187]
Pelican Cove 3
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC3]
Pelican Cove 10
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Bayfront
[PC10]
Bradenton Beach Club 249
From $214/night
Bed & Bath: 3/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC249]
5003 Arlington Rd
From $250/night
Bed & Bath: 3/2
Sleeps: 6
Location: Palmetto
View: Bayfront
[5003]
Fountain Head 8
From $135/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[FH8]
Runaway Bay 164
From $96/night
Bed & Bath: 1/1
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB164]
3011 Ave E-1
From $200/night
Bed & Bath: 4/2
Sleeps: 8
Location: Holmes Beach
View: Near Beach
[3011-1]
West Bay Point Moorings 193
From $117/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View:
[WBPM193]
Anna Maria Island Club 12
From $224/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC12]
Club Bamboo South 301
From $165/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View:
[Bamboo 301]
Pelican Cove 1
From $225/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[PC1]
Villas-206
From $236/night
Bed & Bath: 3/3½
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[Villas-206]
516 70th St
From $375/night
Bed & Bath: 4/4
Sleeps: 9
Location: Holmes Beach
View: Canal
[516 70th St]
Runaway Bay 230
From $129/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB230]
Coquina Moorings 201
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[CM-201]
405 Bay Palms
From $193/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[405 Bay]
Harbor Lane 2 Tranquility
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane2]
Sunbow Bay 108
From $133/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Bayfront
[Sbb108]
Island Beach Club 1
From $214/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC1]
LaPlayita Condo
From $114/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[LAPLAY5]
Island Beach Club 3
From $169/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC3]
8201 Gulf Dr
From $257/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[8201 Gulf Dr]
Martinique 207 South
From $214/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[Mart 207]
North Beach Village 63
From $143/night
Bed & Bath: 2/2½
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[6250 Holmes]
West Bay Point Moorings 294
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[WBPM 294]
West Bay Point Moorings 155
From $110/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View:
[WBPM 155]
Pelican Cove 2
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC2]
Harbor Lane 3 Sanctuary
From $115/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[HarborLane3]
Gulf Watch 210
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW210]
Club Bamboo South 119 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 119]
Bay View Condo C
From $186/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[BVC]
614 Concord Lane
From $217/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Canal
[614CONCORD]
744 Jacaranda Rd
From $275/night
Bed & Bath: 3/3
Sleeps: 6
Location: Anna Maria
View: Near Beach
[744JAC]
211 83rd Street
From $214/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View:
[211 83rd St]
Bay View Condo H
From $207/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[BVH]
Bradenton Beach Club 248
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc248]
Anna Maria Island Club 45
From $307/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC45]
147 50th Street
From $299/night
Bed & Bath: 4/3
Sleeps: 8
Location: Holmes Beach
View:
[147 50th St]
Coquina Beach Club 102
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC102]
Gulf Watch 111
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW111]
Bradenton Beach Club 230
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC230]
Coquina Beach Club 202
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC202]
Bridgeport 215
From $164/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[BP215]
Bay View Condo A
From $200/night
Bed & Bath: 2/2
Sleeps: 8
Location: Bradenton Beach
View: Near Beach
[BVA]
WestChester LBK 304A
From $150/night
Bed & Bath: 2/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[WestChester]
609 Concord Lane
From $229/night
Bed & Bath: 3/2
Sleeps: 5
Location: Holmes Beach
View: Canal
[609 Concord]
Runaway Bay 261
From $114/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB261]
Sandy Point 205
From $114/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[SP205]
Tropical Sunset 2
From $143/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[Trop Sunset2]
2206 Ave C
From $357/night
Bed & Bath: 4/2
Sleeps: 8
Location: Bradenton Beach
View: Near Beach
[2206 Ave C]
Pelican Cove 8
From $225/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[PC8]
Island Village
From $85/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[IV215]
Club Bamboo South 225 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 225]
Gulf Watch 104
From $136/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[GW104]
Martinique 306 South
From $117/night
Bed & Bath: 2/2
Sleeps: 5
Location: Holmes Beach
View: Beachfront
[Mart306]
Island Beach Club 4
From $186/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC4]
West Bay Cove 222
From $129/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[WBC 600]
529 Key Royale Drive
From $521/night
Bed & Bath: 6/5
Sleeps: 12
Location: Holmes Beach
View: Canal
[529 Key]
Runaway Bay 115
From $96/night
Bed & Bath: 1/1
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[RAB115]
Pelican Cove 6
From $225/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[PC6]
Club Bamboo South 121 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 121]
Sandy Point Cove 114
From $129/night
Bed & Bath: 3/3
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[SPC114]
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]
217 84th Street
From $186/night
Bed & Bath: 3/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[217 84TH]
Gulf Watch 216
From $150/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[GW216]
518 71st St--Palm Paradise
From $233/night
Bed & Bath: 3/2
Sleeps: 6
Location: Holmes Beach
View: Canal
[518 71st]
Pelican Cove 14
From $225/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC14]
210-1 Haverkos
From $100/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[210-1 Hav]
Runaway Bay 174
From $129/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[RAB 174]
Pelican Cove 9
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Bayfront
[PC9]
Bradenton Beach Club 252
From $186/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[Bradbc252]
Sandy Point Cove 112
From $114/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[SPC112]
Cayman 104
From $143/night
Bed & Bath: 2/2
Sleeps: 5
Location: Holmes Beach
View: Near Beach
[Cayman 104]
510 Bayview
From $529/night
Bed & Bath: 5/5
Sleeps: 10
Location: Holmes Beach
View: Canal
[510Bayview]
Martinique 505 South
From $129/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Beachfront
[Mart 505]
3011 Ave E-3
From $140/night
Bed & Bath: 1/1
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[3011-3]
707 N Bay The Shell House
From $275/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Anna Maria
View: Near Beach
[707BAY]
7717 27th Ave W-Chili Cove
From $229/night
Bed & Bath: 4/2½
Sleeps: 10
Location: Bradenton
View:
[7717 27th]
Fountain Head 6
From $135/night
Bed & Bath: 2/1½
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[FH6]
Club Bamboo South 220 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 220]
Harbor Lane 4 Harmony
From $144/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Near Beach
[HarborLane4]
Gulf View Townhouses 3
From $150/night
Bed & Bath: 2/2½
Sleeps: 4
Location: Holmes Beach
View: Near Beach
[GVT3]
Island Beach Club 22
From $171/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC22]
Sunplaza 115
From $357/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[Sunplaza 115]
Island Beach Club 24
From $186/night
Bed & Bath: 2/1
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC24]
Coquina Beach Club 103
From $221/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Beachfront
[CBC103]
Sunbow Bay A1
From $193/night
Bed & Bath: 3/3
Sleeps: 8
Location: Holmes Beach
View: Near Beach
[SbbA1]
Island Beach Club 21
From $171/night
Bed & Bath: 2/2
Sleeps: 4
Location: Holmes Beach
View: Beachfront
[IBC21]
West Bay Point Moorings 42
From $150/night
Bed & Bath: 2/2
Sleeps: 6
Location: Holmes Beach
View: Bayfront
[WBPM 42]
Bradenton Beach Club 251
From $214/night
Bed & Bath: 3/2½
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[BradBC251]
Pelican Cove 5
From $225/night
Bed & Bath: 2/2
Sleeps: 5
Location: Bradenton Beach
View: Near Beach
[PC5]
Seascape Unit 103
From $214/night
Bed & Bath: 3/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[SEASCAPE103]
Gulf Watch 211
From $136/night
Bed & Bath: 2/2
Sleeps: 6
Location: Bradenton Beach
View: Near Beach
[GW211]
Anna Maria Island Club 31
From $236/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[AMIC31]
10316Spoonbill-Casa in the Cay
From $236/night
Bed & Bath: 4/3
Sleeps: 8
Location: Bradenton
View:
[10316 Spoon]
Pelican Cove 11
From $225/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Bayfront
[PC11]
620 Gladstone
From $386/night
Bed & Bath: 4/3
Sleeps: 7
Location: Holmes Beach
View: Canal
[620 Gladston]
4004 5th Ave
From $225/night
Bed & Bath: 4/4
Sleeps: 9
Location: Holmes Beach
View: Near Beach
[4004 5th Ave]
Coquina Beach Club 206
From $221/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[CBC206]
Gulf Watch 205
From $136/night
Bed & Bath: 2/2
Sleeps: 4
Location: Bradenton Beach
View: Near Beach
[GW205]
WestChester LBK205A
From $233/night
Bed & Bath: 2/2
Sleeps: 6
Location: Longboat Key
View: Beachfront
[WestChester2]
Club Bamboo South 120 Studio
From $145/night
Bed & Bath: Studio/1
Sleeps: 4
Location: Bradenton Beach
View: Beachfront
[Bamboo 120]
