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.

2206 Ave C
2206 Ave C
Bed & Bath: 4/2 Sleeps: 8 Location: Bradenton Beach View: Near Beach
[2206 Ave C]
Bradenton Beach Club A
Bradenton Beach Club A
Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront
[Bradbc-A]
Gulf View 103
Gulf View 103
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[GV103]
Sunplaza 115
Sunplaza 115
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[Sunplaza 115]
707 N Bay The Shell House
707 N Bay The Shell House
Bed & Bath: 3/2½ Sleeps: 6 Location: Anna Maria View: Near Beach
[707BAY]
Club Bamboo South 220 Studio
Club Bamboo South 220 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 220]
Bay View Condo A
Bay View Condo A
Bed & Bath: 2/2 Sleeps: 8 Location: Bradenton Beach View: Bayfront
[BVA]
Harbor Lane 3 Sanctuary
Harbor Lane 3 Sanctuary
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach
[HarborLane3]
Sandy Point Cove 112
Sandy Point Cove 112
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[SPC112]
Sandy Point 109
Sandy Point 109
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[SP109]
3011 Ave E-2
3011 Ave E-2
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[3011-2]
Harbor Lane 1 Serenity
Harbor Lane 1 Serenity
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach
[HarborLane1]
210-2 Haverkos
210-2 Haverkos
Bed & Bath: 2/1½ Sleeps: 4 Location: Holmes Beach View:
[210-2 Hav]
Bay View Condo D
Bay View Condo D
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[BVD]
210-1 Haverkos
210-1 Haverkos
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach
[210-1 Hav]
Bradenton Beach Club 247
Bradenton Beach Club 247
Bed & Bath: 3/2½ Sleeps: 6 Location: Bradenton Beach View: Near Beach
[BradBC247]
Bradenton Beach Club 238
Bradenton Beach Club 238
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[Bradbc238]
Anna Maria Island Club 45
Anna Maria Island Club 45
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC45]
Shorewalk 104
Shorewalk 104
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton View:
[ShoreW104]
Anna Maria Island Club 14
Anna Maria Island Club 14
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC14]
Bradenton Beach Club 251
Bradenton Beach Club 251
Bed & Bath: 3/2½ Sleeps: 6 Location: Bradenton Beach View: Near Beach
[BradBC251]
Coquina Beach Club 206
Coquina Beach Club 206
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[CBC206]
Coquina Beach Club 102
Coquina Beach Club 102
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront
[CBC102]
Runaway Bay 261
Runaway Bay 261
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[RAB261]
3011 Ave E-3
3011 Ave E-3
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach
[3011-3]
Beach View 8
Beach View 8
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View:
[BeachView 8]
Townhomes in the Cay
Townhomes in the Cay
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[THC A1]
Island Beach Club 22
Island Beach Club 22
Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach View: Beachfront
[IBC22]
Bradenton Beach Club 222
Bradenton Beach Club 222
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[Bradbc222]
211 83rd Street
211 83rd Street
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View:
[211 83rd St]
Runaway Bay 187
Runaway Bay 187
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Bayfront
[RAB187]
Martinique 308 South
Martinique 308 South
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[Mart 308]
Club Bamboo South 123 Studio
Club Bamboo South 123 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 123]
518 71st St--Palm Paradise
518 71st St--Palm Paradise
Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Canal
[518 71st]
Bay View Condo H
Bay View Condo H
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[BVH]
408 Beachy Keen
408 Beachy Keen
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria View: Near Beach
[408ALAM]
Bay View Condo C
Bay View Condo C
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[BVC]
405 Bay Palms
405 Bay Palms
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach
[405 Bay]
Coquina Beach Club 103
Coquina Beach Club 103
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront
[CBC103]
Sunset Terrace 203
Sunset Terrace 203
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[SST203]
Bradenton Beach Club 249
Bradenton Beach Club 249
Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[BradBC249]
Pelican Cove 14
Pelican Cove 14
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[PC14]
Club Bamboo South 122 Studio
Club Bamboo South 122 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 122]
Runaway Bay 230
Runaway Bay 230
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[RAB230]
Anna Maria Island Club 38
Anna Maria Island Club 38
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC38]
Pelican Cove 5
Pelican Cove 5
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach
[PC5]
Anna Maria Island Club 12
Anna Maria Island Club 12
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC12]
7717 27th Ave W-Chili Cove
7717 27th Ave W-Chili Cove
Bed & Bath: 4/2½ Sleeps: 10 Location: Bradenton View:
[7717 27th]
Gulf Watch 210
Gulf Watch 210
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[GW210]
Bradenton Beach Club 230
Bradenton Beach Club 230
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[BradBC230]
Sandy Point Cove 114
Sandy Point Cove 114
Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach View: Near Beach
[SPC114]
Pelican Cove 4
Pelican Cove 4
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach
[PC4]
Pelican Cove 10
Pelican Cove 10
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Bayfront
[PC10]
Coquina Moorings 201
Coquina Moorings 201
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[CM-201]
637 Norton
637 Norton
Bed & Bath: 4/3½ Sleeps: 8 Location: Longboat Key View: Canal
[637 Norton]
La Playita Condo 2
La Playita Condo 2
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[LAPLAY2]
Coquina Reef 15
Coquina Reef 15
Bed & Bath: 1/1 Sleeps: 4 Location: Bradenton Beach View:
[CR15]
Club Bamboo South 225 Studio
Club Bamboo South 225 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 225]
West Bay Point Moorings 155
West Bay Point Moorings 155
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View:
[WBPM 155]
Sunbow Bay 212
Sunbow Bay 212
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[SBB212]
313 Island Walk
313 Island Walk
Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[313 64th]
Harbor Lane 2 Tranquility
Harbor Lane 2 Tranquility
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach View: Near Beach
[HarborLane2]
Bradenton Beach Club 228
Bradenton Beach Club 228
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[Bradbc228]
Gulf Watch 211
Gulf Watch 211
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[GW211]
Island Beach Club 1
Island Beach Club 1
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[IBC1]
Gulf Watch 111
Gulf Watch 111
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach
[GW111]
Gulf View Townhouses 3
Gulf View Townhouses 3
Bed & Bath: 2/2½ Sleeps: 4 Location: Holmes Beach View: Near Beach
[GVT3]
Gulf Watch 104
Gulf Watch 104
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[GW104]
7520 3rd Ave-Sandy Pines
7520 3rd Ave-Sandy Pines
Bed & Bath: 3/2 Sleeps: 8 Location: Bradenton View:
[7520 3rd Ave]
Shorewalk 101
Shorewalk 101
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton View:
[ShoreW101]
Pelican Cove 12
Pelican Cove 12
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[PC12]
Sabal Palms 1AG
Sabal Palms 1AG
Bed & Bath: 1/1½ Sleeps: 4 Location: Bradenton View:
[Sabal 1AG]
Fountain Head 6
Fountain Head 6
Bed & Bath: 2/1½ Sleeps: 4 Location: Holmes Beach View: Near Beach
[FH6]
Club Bamboo South 301
Club Bamboo South 301
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[Bamboo 301]
Pelican Cove 1
Pelican Cove 1
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[PC1]
Pelican Cove 9
Pelican Cove 9
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Bayfront
[PC9]
Gulf Watch 216
Gulf Watch 216
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[GW216]
Club Bamboo South 121 Studio
Club Bamboo South 121 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 121]
Pelican Cove 11
Pelican Cove 11
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[PC11]
Martinique 207 South
Martinique 207 South
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[Mart 207]
Shorewalk The Palms 205
Shorewalk The Palms 205
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[ShoreW205]
LaPlayita Condo 5
LaPlayita Condo 5
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach
[LAPLAY5]
Pelican Cove 8
Pelican Cove 8
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[PC8]
Sandy Point 111
Sandy Point 111
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach
[SP111]
Martinique 306 South
Martinique 306 South
Bed & Bath: 2/2 Sleeps: 5 Location: Holmes Beach View: Beachfront
[Mart306]
811Audubon
811Audubon
Bed & Bath: 3/2 Sleeps: 6 Location: Bradenton View:
[811Audubon]
Meadow Croft 5714
Meadow Croft 5714
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[Meadow 5714]
Pelican Cove 13
Pelican Cove 13
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Bayfront
[PC13]
Island Beach Club 24
Island Beach Club 24
Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach View: Beachfront
[IBC24]
Cayman 104
Cayman 104
Bed & Bath: 2/2 Sleeps: 5 Location: Holmes Beach View: Near Beach
[Cayman 104]
609 Concord Lane
609 Concord Lane
Bed & Bath: 3/2 Sleeps: 5 Location: Holmes Beach View: Canal
[609 Concord]
Sandy Point 204
Sandy Point 204
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach
[SP204]
Runaway Bay 205
Runaway Bay 205
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[RAB205]
Gulf Watch 205
Gulf Watch 205
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[GW205]
Pelican Cove 2
Pelican Cove 2
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach
[PC2]
Runaway Bay 115
Runaway Bay 115
Bed & Bath: 1/1 Sleeps: 4 Location: Bradenton Beach View: Near Beach
[RAB115]
3011 Ave E-1
3011 Ave E-1
Bed & Bath: 4/2 Sleeps: 8 Location: Holmes Beach View: Near Beach
[3011-1]
Anna Maria Island Club 31
Anna Maria Island Club 31
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC31]
Fountain Head 8
Fountain Head 8
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[FH8]
Gulf Watch 115
Gulf Watch 115
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Bayfront
[GW115]
Beach Castle Resort 6
Beach Castle Resort 6
Bed & Bath: 2/2 Sleeps: 6 Location: Longboat Key View: Beachfront
[BC-6]
146 Wild Palm
146 Wild Palm
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[146 Wild]
Island Beach Club 3
Island Beach Club 3
Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach View: Beachfront
[IBC3]
Anna Maria Island Club 26
Anna Maria Island Club 26
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[AMIC26]
Island Beach Club 21
Island Beach Club 21
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[IBC21]
538 70th St
538 70th St
Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach View: Bayfront
[538 70th]
West Bay Point Moorings 42
West Bay Point  Moorings 42
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Bayfront
[WBPM 42]
Runaway Bay 174
Runaway Bay 174
Bed & Bath: 2/2 Sleeps: 5 Location: Bradenton Beach View: Near Beach
[RAB 174]
Shorewalk 202-1
Shorewalk 202-1
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[ShoreW202-1]
882 Audubon
882 Audubon
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton View:
[882-Audubon]
Runaway Bay 248
Runaway Bay 248
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Near Beach
[RAB248]
Harbor Lane 4 Harmony
Harbor Lane 4 Harmony
Bed & Bath: 2/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[HarborLane4]
Martinique 203 North
Martinique 203 North
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[Mart 203]
Club Bamboo South 125 Studio
Club Bamboo South 125 Studio
Bed & Bath: Studio/1 Sleeps: 4 Location: Bradenton Beach View: Beachfront
[Bamboo 125]
Coquina Beach Club 202
Coquina Beach Club 202
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach View: Beachfront
[CBC202]
217 84th Street
217 84th Street
Bed & Bath: 3/2 Sleeps: 6 Location: Holmes Beach View: Near Beach
[217 84TH]
Club Bamboo South 119 Studio
Club Bamboo South 119 Studio
Bed & Bath: Studio/1 Sleeps: 3 Location: Bradenton Beach View: Beachfront
[Bamboo 119]
510 Bayview
510 Bayview
Bed & Bath: 5/5 Sleeps: 10 Location: Holmes Beach View: Canal
[510Bayview]
Martinique 505 South
Martinique 505 South
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Beachfront
[Mart 505]
Sandy Point Cove 106
Sandy Point Cove 106
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach View: Near Beach
[SPC106]
517 Key Royale
517 Key Royale
Bed & Bath: 5/5 Sleeps: 10 Location: Holmes Beach View: Canal
[517 Key]
Sandy Point 205
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!

Holmes Beach Weather Info
Holmes Beach Office
On Anna Maria Island
5201 Gulf Drive
Holmes Beach, Florida USA 34217
941-778-4800
Se Habla Español | Wir sprechen Deutsch
Ellenton Office
Located in Ellenton Plaza
945 25th Drive East, Suite 10
Ellenton, Florida USA 34222
941-729-2381
Questions or Comments?
We want to hear from you!
Please call with any of your questions or concerns. Our friendly staff is here to help. Call or email us at info@paradiserealty.com.
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