Montgomery Cottages - Vacation Rentals in Island Players

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From US $479

         

9.8 (295 Reviews)

Cottage

Charming cottage in quiet area, close to beach & bay.

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $425

         

|

10.0 (1 Review)

House

Coconut Cottage #4 by AMI Locals

• Pet Friendly
• Pool
• Child Friendly

• Sarasota
• Holmes Beach

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From US $300

         

9.8 (47 Reviews)

Cottage

Tropical Landscaped Beach Cottage with Heated Jetted Pool

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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From US $383

         

9.8 (76 Reviews)

Cottage

Charming 2br/1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

• Air Conditioner
• Parking
• TV

• Sarasota
• Anna Maria

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From US $195

         

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New

House

Coconut Cottage #3 by AMI Locals

• Pet Friendly
• Pool
• Child Friendly

• Sarasota
• Holmes Beach

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From US $384

         

|

New

Cottage

Serenity Cottage

• Air Conditioner
• Pool
• Balcony/Terrace

• Sarasota
• Anna Maria

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From US $279

         

9.8 (37 Reviews)

Cottage

GREAT COTTAGE w/Heated Pool, Dog- See Note - Allowed, FREE WiFi/Trolley, Steps to Beach, Dining.

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Ilexhurst

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From US $1,026

         

|

10.0 (2 Reviews)

House

Coconut Lagoon - Lovely Historic Renovated Cottage wHuge Heated Pool Backyard OasisCabanaBar

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $428

         

9.6 (120 Reviews)

Cottage

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

• Air Conditioner
• Parking
• TV

• Sarasota
• Anna Maria

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From US $489

         

10.0 (10 Reviews)

Cottage

Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $331

         

10.0 (15 Reviews)

Cottage

Holmes Beach Cottage Steps to the Beach with Heated Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $411

         

10.0 (17 Reviews)

Cottage

Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $353

         

10.0 (13 Reviews)

Cottage

Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $331

         

10.0 (14 Reviews)

Cottage

Beautiful cottage just around the corner from the beach with Private Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $346

         

10.0 (8 Reviews)

Cottage

Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $381

         

10.0 (2 Reviews)

Cottage

Ground Floor home for 5, short walk to beach and private heated pool! Lovely open living area

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $396

         

10.0 (2 Reviews)

Cottage

Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Holmes Beach

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From US $641

         

9.8 (47 Reviews)

Cottage

Prices cut by 20% for stays up to 31.01.26 - Starfish Cottage

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $307

         

9.8 (41 Reviews)

Cottage

Prices cut by 20% for stays up to 31.01.26 - Shell Cottage

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $412

         

10.0 (127 Reviews)

Cottage

Private Pool - Seaglass Cottage by SeaBreeze Vacation

• Air Conditioner
• Parking
• Pool

• Sarasota
• Anna Maria

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From US $485

         

10.0 (288 Reviews)

Cottage

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

• Air Conditioner
• Parking
• Pet Friendly

• Sarasota
• Anna Maria

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From US $319

         

10.0 (90 Reviews)

Cottage

Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

• Air Conditioner
• Parking
• TV

• Sarasota
• Holmes Beach

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From US $138

         

10.0 (70 Reviews)

Cottage

Quiet Nights of Quiet Stars on Anna Maria Island

• Air Conditioner
• Parking
• TV

• Sarasota
• Holmes Beach

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From US $482

         

10.0 (48 Reviews)

Cottage

Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!

• Air Conditioner
• Pet Friendly
• Pool

• Sarasota
• Anna Maria

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★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Island Players.