Vacation Rentals with Pool in Anna Maria City Pier, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Anna Maria City Pier

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3434 Best Vacation Rentals with Pool in Anna Maria City Pier (Starting from $191)

AM I Dreaming
AM I Dreaming
House
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$930
Average price / night
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Amazing 6 bed house on Anna Maria! Putt putt, heated pool and spa!
Amazing 6 bed house on Anna Maria! Putt putt, heated pool and spa!
House
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry

6 Bedrooms12 Guests
9.8

Exceptional

12 reviews

$2189
Average price / night
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Bay Breezes at Bayside Bungalow
Bay Breezes at Bayside Bungalow
Villa
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
8.9

Fabulous

6 reviews

$500
Average price / night
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Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av
Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av
Villa
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom4 Guests
9.2

Superb

60 reviews

$608
Average price / night
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Bayside Cutie at Bayside Bungalow
Bayside Cutie at Bayside Bungalow
Villa
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
6.2

Good

6 reviews

$619
Average price / night
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Beautiful Bungalow with Pool and Bay Views!
Beautiful Bungalow with Pool and Bay Views!
Villa
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom6 Guests
9.6

Exceptional

41 reviews

$649
Average price / night
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Barefoot by the Bay at Bayside Bungalow
Barefoot by the Bay at Bayside Bungalow
Villa
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
8.0

Good

5 reviews

$447
Average price / night
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Bayside Retreat with Pool and Bay Views! Near Beaches, Shops, and Dining
Bayside Retreat with Pool and Bay Views! Near Beaches, Shops, and Dining
Villa
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
9.6

Exceptional

75 reviews

$879
Average price / night
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Blissful Bay at Bayside Bungalow
Blissful Bay at Bayside Bungalow
Villa
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
9.4

Superb

7 reviews

$670
Average price / night
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Bayfront Bliss! Pool, BBQ and Dolphin Views!
Bayfront Bliss! Pool, BBQ and Dolphin Views!
Villa
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
9.4

Superb

96 reviews

$928
Average price / night
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Bay Vista at Bayside Bungalow
Bay Vista at Bayside Bungalow
Villa
Anna Maria, FL, USA
0.1k from Anna Maria City Pier center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$974
Average price / night
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Resort-Style Pool Steps from the Bay and Pine Ave!
Resort-Style Pool Steps from the Bay and Pine Ave!
Villa
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

53 reviews

$799
Average price / night
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AM I Dreaming by AMI Locals
AM I Dreaming by AMI Locals
House
Anna Maria City Pier, Anna Maria, Florida, USA
0.1k from Anna Maria City Pier center

Parking, Internet, Kitchen, Pet Friendly, Pool, Private Pool, Wheelchair Accessible

3 Bedrooms6 Guests
New to Booking
$425
Average price / night
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Luxe AMI Stay! Saltwater Pool and Rooftop Views
Luxe AMI Stay! Saltwater Pool and Rooftop Views
House
Anna Maria, FL, 34216, United States
0.1k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
9.2

Superb

28 reviews

$1370
Average price / night
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Bayside Bungalows by AMI Locals
Bayside Bungalows by AMI Locals
Villa
Anna Maria City Pier, Anna Maria, Florida, USA
0.1k from Anna Maria City Pier center

Parking, Kitchen, Pet Friendly, Internet, Laundry, Pool, Child Friendly

10 Bedrooms28 Guests
8.0

Good

6 reviews

$225
Average price / night
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Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green
Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$1570
Average price / night
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Sunrise Garden Resort
Sunrise Garden Resort
Apartment
Anna Maria, FL, USA
0.2k from Anna Maria City Pier center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Self-catering, Accessible hotels, Beach rentals

22 Bedrooms65 Guests
8.0

Good

178 reviews

$378
Average price / night
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Magnolia Cottage: Private Pool, Near Beaches & Pine Ave
Magnolia Cottage: Private Pool, Near Beaches & Pine Ave
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
9.8

Exceptional

7 reviews

$917
Average price / night
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South Bay Inn 4
South Bay Inn 4
Apartment
Anna Maria, FL, USA
0.2k from Anna Maria City Pier center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$191
Average price / night
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Luxury Beach House with Bay Views and Pool
Luxury Beach House with Bay Views and Pool
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$1833
Average price / night
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Blue Bay
Blue Bay
House
Anna Maria, FL, USA
0.2k from Anna Maria City Pier center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

8 Bedrooms18 Guests
New to Booking
$2214
Average price / night
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Bayfront Beach access with Heated Pool!
Bayfront Beach access with Heated Pool!
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$680
Average price / night
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Sea La Vie by Duncan Real Estate
Sea La Vie by Duncan Real Estate
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
New to Booking
$768
Average price / night
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Decked Out: Steps to Bay & Beach, Pool, Games by Anna Maria Life Vacation Rentals
Decked Out: Steps to Bay & Beach, Pool, Games by Anna Maria Life Vacation Rentals
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
9.4

Superb

3 reviews

$761
Average price / night
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5BR Beach House • Pool • Walk to Pine Ave & Dining
5BR Beach House • Pool • Walk to Pine Ave & Dining
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$1842
Average price / night
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Anapauo Beachhouse: Million dollar views of Tampa Bay!
Anapauo Beachhouse: Million dollar views of Tampa Bay!
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.8

Exceptional

42 reviews

$1310
Average price / night
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Dream Luxury Vacation Home with a Guest House, Private Pool, and Bay Views!
Dream Luxury Vacation Home with a Guest House, Private Pool, and Bay Views!
House
Anna Maria, FL, 34216, United States
0.2k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

8 Bedrooms18 Guests
8.8

Fabulous

45 reviews

$1784
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Anna Maria City Pier.

Where to stay in Anna Maria City Pier? Best neighborhoods & areas

Anna Maria City Pier Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3434 verified vacation rentals with a pool in Anna Maria City Pier. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Anna Maria City Pier vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $191 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Anna Maria City Pier offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Anna Maria City Pier welcome pets. Currently, 55 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Anna Maria City Pier often include additional outdoor features such as Pool, Internet, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Anna Maria City Pier offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.