Unplugged Weekend - Vacation Rentals in Anna Maria City Pier

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From US $921

         

10.0 (131 Reviews)

House

Luxury on Gulf of Mexico, Heated Pool/Spa *50% OFF* Golf Cart booked B4 1/31/26!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $834

         

|

10.0 (2 Reviews)

Apartment

La Casa Karen

• Air Conditioner
• Pool
• View

• Sarasota
• Holmes Beach

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From US $368

         

|

8.6 (650 Reviews)

Resort

Bali Hai Beachfront Resort and Spa

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $2,076

         

10.0 (109 Reviews)

House

Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak, SUPs & MORE

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $805

         

10.0 (1 Review)

House

A Bean Point Paradise - 5 beds and 4,5 bathrooms in Anna Maria

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $944

         

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New

House

Anna Maria Beach Serenity

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $311

         

10.0 (5 Reviews)

Condo

Beach Front 2 bedroom condo on AMI with pool!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $783

         

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10.0 (1 Review)

House

Heavenly Holly

• Air Conditioner
• Pool
• View

• Sarasota
• Anna Maria

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From US $348

         

New

House

Serenity Cottage

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $533

         

9.4 (9 Reviews)

House

Ebb Tide by Duncan Real Estate

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $774

         

8.4 (5 Reviews)

House

New Luxury Getaway on Anna Maria Island

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $3,937

         

10.0 (1 Review)

House

Luxurious Shangri-La Home with Pool, Spa, & Rooftop Deck on Anna Maria Island

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $508

         

9.8 (111 Reviews)

House

Charming Beach Home-w/large Pool - Only 3 Houses from the Beach, Near Pine Ave!!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $481

         

10.0 (33 Reviews)

House

Luxury home just 2 blocks to beach, private pool and spa!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $425

         

9.8 (23 Reviews)

House

Gorgeous house with a private pool/spa! Bonus loft for kids!

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Holmes Beach

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From US $1,009

         

9.4 (3 Reviews)

House

Black Pearl: 4 BR, 3 BA House in Anna Maria, Sleeps 8

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $372

         

10.0 (129 Reviews)

House

90sec walk to beach, quiet, sunny pool, clean, 500mb, solar system, PS4

• Air Conditioner
• Pool
• View

• Sarasota
• Holmes Beach

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From US $855

         

10.0 (70 Reviews)

House

Coral Castle Luxury Canalfront Home - 5bed/3.5bath private pool - Anna Maria- By

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $500

         

10.0 (56 Reviews)

House

3 BR, 2 BA Home with Private Pool and Spa on the North End of Anna Maria Island

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $1,934

         

10.0 (24 Reviews)

House

Amazing Beachfront home with Beach Access, Pool, and Games! Lazy Loggerhead

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $1,006

         

10.0 (22 Reviews)

House

Luxury home close to beach! Private pool, spa, and putting green!

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $505

         

10.0 (22 Reviews)

House

Family home with Tiki-hut, Pool, Spa, and Waterslide-Day Dream

• Air Conditioner
• Pool
• View

• Sarasota
• Holmes Beach

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From US $435

         

10.0 (11 Reviews)

House

Beautiful Home with Heated Pool and Game Area!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Holmes Beach

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From US $1,289

         

10.0 (9 Reviews)

House

Sprawling Private Beach, Tiki Bar, and Beautiful Pool! Don't miss this property!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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