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  • Castnetter Beach Resort 5
    From $350 per night (USD)

    VRBO

    Castnetter Beach Resort 5

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...

    From $350 per night (USD)

    VRBO

    Details
  • Two Minutes from the Gulf Beaches! Private Pool. Pet Friendly.
    From $203 per night (USD)

    Expedia

    Two Minutes from the Gulf Beaches! Private Pool. Pet Friendly.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Salty Dog is the ideal cozy island home and is located just 2 minutes from the beautiful Gulf beaches! This home includ ...

    From $203 per night (USD)

    Expedia

    Details
  • Beach Front Condo Complex with Spectacular Sunset Views!
    From $904 per night (USD)

    VRBO

    Beach Front Condo Complex with Spectacular Sunset Views!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    La Plage 9 is a gorgeous 3 bedroom and 2.5 bathroom direct Gulf front condo that features incredible views of the Gulf o ...

    From $904 per night (USD)

    VRBO

    Details
  • Updated Canal Front Home with Elevator and Heated Pool/Spa!
    From $718 per night (USD)

    Expedia

    Updated Canal Front Home with Elevator and Heated Pool/Spa!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Beach and Boat House by Anna Maria Island Locals Home in Holmes Beach, FL 1 block from the beach on a natural canal! H ...

    From $718 per night (USD)

    Expedia

    Details
  • Beach Front Condo with Panoramic Views of the Gulf! Heated Pool
    From $626 per night (USD)

    VRBO

    Beach Front Condo with Panoramic Views of the Gulf! Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Island Paradise 1 has the best sunset views in Holmes Beach, from the privacy of your own home! This home includes the ...

    From $626 per night (USD)

    VRBO

    Details
  • Sunset Views from This Beach Front Condo.
    From $351 per night (USD)

    Expedia

    Sunset Views from This Beach Front Condo.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Gulf Shores 106 is a Gulf front condo located in Holmes Beach on Anna Maria Island. Enjoy beautiful spectacular sunset v ...

    From $351 per night (USD)

    Expedia

    Details
  • The Terrace 3 by Duncan Real Estate
    From $225 per night (USD)

    VRBO

    The Terrace 3 by Duncan Real Estate

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The Terrace 3 invites to a great Island vacation! This beautiful, newly renovated 2-bedroom, 2-bath townhouse style cond ...

    From $225 per night (USD)

    VRBO

    Details
  • Dream vacation-Direct Gulf Front Condo
    From $104 per night (USD)

    Expedia

    Dream vacation-Direct Gulf Front Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy wonderful side views of the Gulf waters and beaches right from the comfort of your living room. Just steps away fr ...

    From $104 per night (USD)

    Expedia

    Details
  • Casa Sierra 203B - 2BR Condo with Pool
    From $189 per night (USD)

    VRBO

    Casa Sierra 203B - 2BR Condo with Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. Th ...

    From $189 per night (USD)

    VRBO

    Details
  • Sugaree -  2bedroom Private Pool Property in Holmes Beach
    From $135 per night (USD)

    Expedia

    Sugaree - 2bedroom Private Pool Property in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Anna Maria Island vacation rental offers one king bed, two twin beds and a queen sleeper sofa all covered in premiu ...

    From $135 per night (USD)

    Expedia

    Details
  • DIRECT GULFRONT CONDO - 1BR/1BA Condo with pool
    From $462 per night (USD)

    VRBO

    DIRECT GULFRONT CONDO - 1BR/1BA Condo with pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    “The Coconuts Beach Resort 108” is a 1 bed 1 bath beach front condo, nestled in the heart of Holmes Beach. Apart of the ...

    From $462 per night (USD)

    VRBO

    Details
  • DIRECT GULFRONT CONDO - 2BR/2BA Condo with pool and rooftop terrace
    From $264 per night (USD)

    Expedia

    DIRECT GULFRONT CONDO - 2BR/2BA Condo with pool and rooftop terrace

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Located in beautiful Holmes Beach, “Ocean Park Terrace” is the perfect Anna Maria Island vacation rental for 5 guests ri ...

    From $264 per night (USD)

    Expedia

    Details
  • Beach View. Beautiful Vacation Destination
    From $547 per night (USD)

    VRBO

    Beach View. Beautiful Vacation Destination

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enc ...

    From $547 per night (USD)

    VRBO

    Details
  • Beach Front Condo with Sunset Views!
    From $484 per night (USD)

    Expedia

    Beach Front Condo with Sunset Views!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    La Plage, unit # 7, it just does not get any better than this direct Gulf front, 3rd-floor corner unit. Located in the p ...

    From $484 per night (USD)

    Expedia

    Details
  • Directly Across the Street from White Sand Beaches! Huge Deck for sunsets!
    From $423 per night (USD)

    VRBO

    Directly Across the Street from White Sand Beaches! Huge Deck for sunsets!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    -Newly Renovated North Beach Village End Unit -Wrap around balcony with seating and great views -1 King, 1 Queen, 2 Twin ...

    From $423 per night (USD)

    VRBO

    Details
  • Newly renovated pool home, tiki hut and close to beach!
    From $550 per night (USD)

    Expedia

    Newly renovated pool home, tiki hut and close to beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Chapter II! This newly renovated 3 bedroom 2 bathroom home is the perfect beach escape! The ground level prop ...

    From $550 per night (USD)

    Expedia

    Details
  • Adorable cottage just across the street from the beach! Private pool!
    From $390 per night (USD)

    VRBO

    Adorable cottage just across the street from the beach! Private pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Coconut Cottage #2 By Anna Maria Island Locals Condo in Holmes Beach, FL Located across the street from the Manatee Pub ...

    From $390 per night (USD)

    VRBO

    Details
  • Sunbow Bay 213 - gorgeous 2 bed/2 bath condo in excellent location
    From $162 per night (USD)

    Expedia

    Sunbow Bay 213 - gorgeous 2 bed/2 bath condo in excellent location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    You will enjoy this 2 bedroom/2 bath condo that is part of the well maintained Sunbow Bay Condominiums with a heated com ...

    From $162 per night (USD)

    Expedia

    Details
  • Kiwi Cottage - Private Heated Pool +Spa+Walk to the Beach!
    From $349 per night (USD)

    VRBO

    Kiwi Cottage - Private Heated Pool +Spa+Walk to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Kiwi Coastal Cottage is under new ownership and every space has been thoughtfully redecorated with a cozy coastal island ...

    From $349 per night (USD)

    VRBO

    Details
  • Condo located Across from Gulf Beaches
    From $200 per night (USD)

    Expedia

    Condo located Across from Gulf Beaches

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Booking minimum 2 weeks. Come sneak away to our cozy retreat in the middle of Holmes Beach! This beautiful 2 bedroom, 2 ...

    From $200 per night (USD)

    Expedia

    Details
  • Island Retreat - Beach House Real Estate
    From $466 per night (USD)

    VRBO

    Island Retreat - Beach House Real Estate

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    At A Glance Luxury Island style home Two minute stroll to the beach Tropical heated pool/Tiki Bar West-facing, view of ...

    From $466 per night (USD)

    VRBO

    Details
  • Private home with Heated Pool Only a short walk to the White Sandy Beaches
    From $264 per night (USD)

    Expedia

    Private home with Heated Pool Only a short walk to the White Sandy Beaches

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Los Arcos de Canasi is a stunning three-bedroom, three-bathroom private home with heated pool located in Bradenton Beach ...

    From $264 per night (USD)

    Expedia

    Details
  • Blue Water View - Beach House Real Estate
    From $859 per night (USD)

    VRBO

    Blue Water View - Beach House Real Estate

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    At A Glance On our Professional Linen Service Program Beautiful Gulf water views, only 1 minute walk to the beach-locat ...

    From $859 per night (USD)

    VRBO

    Details
  • Coconuts Gulf View #117 - Enjoy pool and beach views! Perfect location on AMI!
    From $472 per night (USD)

    Expedia

    Coconuts Gulf View #117 - Enjoy pool and beach views! Perfect location on AMI!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Construction will be taking place at this complex from August 29-October 1. The pool will be closed from September 10-Oc ...

    From $472 per night (USD)

    Expedia

    Details
  • A Pirate's Dream by AMI Locals - Boat Dock! Canal Front!
    From $1250 per night (USD)

    VRBO

    A Pirate's Dream by AMI Locals - Boat Dock! Canal Front!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to A Pirate's Dream Bring your boat! You will have a jolly good time! The island lifestyle will be hard to lea ...

    From $1250 per night (USD)

    VRBO

    Details
  • Amazing Resort Sixty-Six, Studio
    From $244 per night (USD)

    Expedia

    Amazing Resort Sixty-Six, Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    *** Sanitation/Cleaning Update *** Bluegreen Resorts take great pride in meeting industry standards of cleanliness and ...

    From $244 per night (USD)

    Expedia

    Details
  • Coconuts Gulf View #118, amazing updated 2 bedroom condo from AMI Locals!
    From $495 per night (USD)

    VRBO

    Coconuts Gulf View #118, amazing updated 2 bedroom condo from AMI Locals!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Construction will be taking place at this complex from August 29-October 1. The pool will be closed from September 10-Oc ...

    From $495 per night (USD)

    VRBO

    Details
  • A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
    From $299 per night (USD)

    Expedia

    A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...

    From $299 per night (USD)

    Expedia

    Details
  • Coconuts Beachfront #110, amazing just-updated 1 bedroom beachfront condo!
    From $773 per night (USD)

    VRBO

    Coconuts Beachfront #110, amazing just-updated 1 bedroom beachfront condo!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Construction will be taking place at this complex from August 29-October 1. The pool will be closed from September 10-Oc ...

    From $773 per night (USD)

    VRBO

    Details
  • Beautiful Home In the Heart of Holmes Beach with Heated Pool
    From $447 per night (USD)

    Expedia

    Beautiful Home In the Heart of Holmes Beach with Heated Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Aquamarine Oasis by Anna Maria Island Locals Home in Holmes Beach, FL Just steps from the beach! Highlights: • Well ma ...

    From $447 per night (USD)

    Expedia

    Details
  • Pet Friendly Holmes Beach Condo with Pool - Palm Isle Village 3211
    From $198 per night (USD)

    VRBO

    Pet Friendly Holmes Beach Condo with Pool - Palm Isle Village 3211

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. With ...

    From $198 per night (USD)

    VRBO

    Details
  • Lakeside Beach House 3/2 Pool Home Outdoor Kitchen Close to Beach
    From $266 per night (USD)

    Expedia

    Lakeside Beach House 3/2 Pool Home Outdoor Kitchen Close to Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...

    From $266 per night (USD)

    Expedia

    Details
  • Coconuts Poolside #115, just-updated 1 bedroom condo!
    From $234 per night (USD)

    VRBO

    Coconuts Poolside #115, just-updated 1 bedroom condo!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    *ALL PHOTOS ARE CURRENTLY OF A SIMILAR UNIT AND ARE FOR EXAMPLE ONLY* Construction will be taking place at this complex ...

    From $234 per night (USD)

    VRBO

    Details
  • New listing! Vibrant retreat w/ shared pool, beach access, tennis & ocean view!
    From $359 per night (USD)

    Expedia

    New listing! Vibrant retreat w/ shared pool, beach access, tennis & ocean view!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $359 per night (USD)

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    Details
  • Direct Beach Front, 2 Bd/2 Bath FREE WiFi & Trolley Heated Pool and Awesome...
    From $255 per night (USD)

    VRBO

    Direct Beach Front, 2 Bd/2 Bath FREE WiFi & Trolley Heated Pool and Awesome...

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    **ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom, two b ...

    From $255 per night (USD)

    VRBO

    Details
  • Water-view condo with pools, dock, & fast WiFi - walk to the beach - one dog OK
    From $174 per night (USD)

    Expedia

    Water-view condo with pools, dock, & fast WiFi - walk to the beach - one dog OK

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sunrise Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...

    From $174 per night (USD)

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    Details
  • Beach front view and only steps to the white sandy beach
    From $580 per night (USD)

    VRBO

    Beach front view and only steps to the white sandy beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...

    From $580 per night (USD)

    VRBO

    Details
  • Come relax in paradise under the palms with with private pool & Spa
    From $292 per night (USD)

    Expedia

    Come relax in paradise under the palms with with private pool & Spa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Paradise Palms East is a 2 bedroom 2 bath duplex with its own private heated pool & spa. This property is centrally loca ...

    From $292 per night (USD)

    Expedia

    Details
  • Paradise Palms all you need for your beach getaway with private pool & Spa
    From $415 per night (USD)

    VRBO

    Paradise Palms all you need for your beach getaway with private pool & Spa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Paradise Palms West is a 2 bedroom 2 bath duplex with its own private heated pool & spa. This property is centrally loca ...

    From $415 per night (USD)

    VRBO

    Details
  • Beachfront Coconuts #112 - Gulf Front 1 Bedroom Condo - Amazing Views
    From $611 per night (USD)

    Expedia

    Beachfront Coconuts #112 - Gulf Front 1 Bedroom Condo - Amazing Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Construction will be taking place at this complex from August 29-October 1. The pool will be closed from September 10-Oc ...

    From $611 per night (USD)

    Expedia

    Details
  • Mango Bay - Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room, Bikes, Walk to Beach!
    From $1018 per night (USD)

    VRBO

    Mango Bay - Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room, Bikes, Walk to Beach!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room ...

    From $1018 per night (USD)

    VRBO

    Details
  • Beachy Townhouse 102
    From $271 per night (USD)

    Expedia

    Beachy Townhouse 102

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    VRC19-000284 BEACHY 102- Plenty of room for the whole family , a Spacious 2 bedroom 2.5 Bath Townhouse (1 king in Maste ...

    From $271 per night (USD)

    Expedia

    Details
  • Charming Coastal Duplex in the Heart of Holmes Beach
    From $175 per night (USD)

    VRBO

    Charming Coastal Duplex in the Heart of Holmes Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Starfish Cove B by Anna Maria Island Locals Duplex in Holmes Beach, FL Just a short walk to the island's famous Gulf b ...

    From $175 per night (USD)

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    Details
  • Charming Coastal Duplex in the Heart of Holmes Beach
    From $199 per night (USD)

    Expedia

    Charming Coastal Duplex in the Heart of Holmes Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Starfish Cove A by Anna Maria Island Locals Home in Holmes Beach, FL Highlights: • Shared patio and grilling area • Sh ...

    From $199 per night (USD)

    Expedia

    Details
  • Salty Shamrock is 3 houses from the beach with private heated pool & spa
    From $794 per night (USD)

    VRBO

    Salty Shamrock is 3 houses from the beach with private heated pool & spa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Salty Shamrock Located just steps away from the sugary soft sand and clear ocean water, Salty Shamrock is the Anna Maria ...

    From $794 per night (USD)

    VRBO

    Details
  • Morning Star by AMI Locals
    From $207 per night (USD)

    Expedia

    Morning Star by AMI Locals

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Morning Star~ A charming 3/2 island home situated in a relaxed, beachy neighborhood that is only 2 blocks fr ...

    From $207 per night (USD)

    Expedia

    Details
  • WBC 212 Spacious 2/2 Pool Tennis Condo Close To White Sand Beach Shopping
    From $223 per night (USD)

    VRBO

    WBC 212 Spacious 2/2 Pool Tennis Condo Close To White Sand Beach Shopping

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    VRC20-000174 Westbay Cove 212 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious two bedroo ...

    From $223 per night (USD)

    VRBO

    Details
  • Bring your Family & Friends and enjoy Paradise Palms w/ 2 Private Heated Pools & Spas
    From $832 per night (USD)

    Expedia

    Bring your Family & Friends and enjoy Paradise Palms w/ 2 Private Heated Pools & Spas

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Paradise Palms is the perfect place for families / friends to vacation together yet still have their own private space. ...

    From $832 per night (USD)

    Expedia

    Details
  • Holmes Beach Getaway on Anna Maria Island
    From $100 per night (USD)

    VRBO

    Holmes Beach Getaway on Anna Maria Island

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Adorable and affordable one bedroom apartment on Holmes Beach. Within walking distance to shopping, eateries, beach, the ...

    From $100 per night (USD)

    VRBO

    Details
  • Wonderful Gulf views from open balcony!
    From $390 per night (USD)

    Expedia

    Wonderful Gulf views from open balcony!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Exceptional views from this spacious beach front 3 bedroom, 2 bath townhouse. Enjoy the sounds of the gulf and beach bre ...

    From $390 per night (USD)

    Expedia

    Details
  • FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
    From $249 per night (USD)

    VRBO

    FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...

    From $249 per night (USD)

    VRBO

    Details
  • Island Beach Club 24
    From $263 per night (USD)

    Expedia

    Island Beach Club 24

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. VRC16-000069 Max 1 veh ...

    From $263 per night (USD)

    Expedia

    Details
  • Coconut Breeze by Duncan Real Estate
    From $200 per night (USD)

    VRBO

    Coconut Breeze by Duncan Real Estate

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Coconut Breeze is a beautifully renovated duplex only a short five-minute walk to the beach. Coconut Breeze is finished ...

    From $200 per night (USD)

    VRBO

    Details
  • Island Beach Club 1 in Holmes Beach
    From $225 per night (USD)

    Expedia

    Island Beach Club 1 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745 Beach/Gulf Front - Com ...

    From $225 per night (USD)

    Expedia

    Details
  • BAY PALMS - SPACIOUS POOL HOME WITH WONDERFUL AMENITIES.  WALK TO A GREAT BEACH!  A MUST SEE!
    From $335 per night (USD)

    VRBO

    BAY PALMS - SPACIOUS POOL HOME WITH WONDERFUL AMENITIES. WALK TO A GREAT BEACH! A MUST SEE!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bay Palms..... Exceptional, newer 3 bedroom, 2.5 bath villa located just a short walk to the beach. This wonderful renta ...

    From $335 per night (USD)

    VRBO

    Details
  • AM I Dreaming: 3  BR, 2  BA House in Holmes Beach, Sleeps 6
    From $322 per night (USD)

    Expedia

    AM I Dreaming: 3 BR, 2 BA House in Holmes Beach, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...

    From $322 per night (USD)

    Expedia

    Details
  • Ground level 2 bedroom, 1 bath with great beach views!
    From $425 per night (USD)

    VRBO

    Ground level 2 bedroom, 1 bath with great beach views!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Fins To The Left (South) ... Direct beach front, ground level, duplex with 2 bedrooms, 1 bath on each side. Amenities in ...

    From $425 per night (USD)

    VRBO

    Details
  • Sun Plaza West 105 - Beach House Real Estate
    From $216 per night (USD)

    Expedia

    Sun Plaza West 105 - Beach House Real Estate

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    AT A GLANCE Recently remodeled gulf front condo 2 Bedrooms and 2 Bathrooms with two balconies Complex equipped with a l ...

    From $216 per night (USD)

    Expedia

    Details
  • 217 84th Street in Holmes Beach
    From $195 per night (USD)

    VRBO

    217 84th Street in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...

    From $195 per night (USD)

    VRBO

    Details
  • Wonderful Gulf views from large screened lanai.
    From $529 per night (USD)

    Expedia

    Wonderful Gulf views from large screened lanai.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Caya Casa ... Spacious 3 bedroom, 2 bath gulf front home with shared heated pool and large screened porch overlooking th ...

    From $529 per night (USD)

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    Details
  • WONDERFUL TOWNHOME WITH VIEWS OF THE GULF!  2 BEDROOM, 2.5 BATH WITH HEATED POOL AND EASY WALK TO TH
    From $133 per night (USD)

    VRBO

    WONDERFUL TOWNHOME WITH VIEWS OF THE GULF! 2 BEDROOM, 2.5 BATH WITH HEATED POOL AND EASY WALK TO TH

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    THE SANDY OWL AT HOLMES BEACH Part of the Beach Townhouses complex, #107 The Sandy Owl sits directly across from Manatee ...

    From $133 per night (USD)

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    Details
  • Sands of Time - Beach House Real Estate
    From $782 per night (USD)

    Expedia

    Sands of Time - Beach House Real Estate

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    'Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...

    From $782 per night (USD)

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    Details
  • 3011 Ave E-2 in Holmes Beach
    From $219 per night (USD)

    VRBO

    3011 Ave E-2 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    3011 Avenue E, Unit 2 - Anna Maria Island - Triplex Condo 2 Bedroom/ 2 Bath ground floor, maximum occupancy of 6 people. ...

    From $219 per night (USD)

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    Details
  • Island Beach Club 22
    From $225 per night (USD)

    Expedia

    Island Beach Club 22

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC20-000254 ...

    From $225 per night (USD)

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    Details
  • LIME IN DE COCONUT- DOWNSTAIRS
    From $600 per night (USD)

    VRBO

    LIME IN DE COCONUT- DOWNSTAIRS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    LIME IN DE COCONUT- DOWNSTAIRS..... Adorable, ground level two bedroom, two bath in a 2 unit cottage. Cheery beach de ...

    From $600 per night (USD)

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    Details
  • Island Beach Club 21
    From $240 per night (USD)

    Expedia

    Island Beach Club 21

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000067 ...

    From $240 per night (USD)

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    Details
  • Restored 1920's Anna Maria Island Cottage .  1 block to the beach with no roads to cross! Quaint, ch
    From $210 per night (USD)

    VRBO

    Restored 1920's Anna Maria Island Cottage . 1 block to the beach with no roads to cross! Quaint, ch

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    110 31st St., Holmes Beach, FL 34217 "Almost to the Beach" ... Charming, updated 1920's cottage with 2 bedrooms and 1 b ...

    From $210 per night (USD)

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    Details
  • White Palm - Beach House Real Estate
    From $125 per night (USD)

    Expedia

    White Palm - Beach House Real Estate

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    At a Glance Newly redecorated condo located on the northeastern Bayfront of Anna Maria Island 2 bedrooms and 2 bathroo ...

    From $125 per night (USD)

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    Details
  • Sunnyside of the Beach
    From $616 per night (USD)

    VRBO

    Sunnyside of the Beach

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...

    From $616 per night (USD)

    VRBO

    Details
  • Sandy Point 111 in Holmes Beach
    From $195 per night (USD)

    Expedia

    Sandy Point 111 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Distance to t ...

    From $195 per night (USD)

    Expedia

    Details
  • Lime In De Coconut - Upstairs 1 bedroom, 1 bath shared  pool. Walk to beaches!
    From $255 per night (USD)

    VRBO

    Lime In De Coconut - Upstairs 1 bedroom, 1 bath shared pool. Walk to beaches!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    LIME IN DE COCONUT- UPSTAIRS..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared ...

    From $255 per night (USD)

    VRBO

    Details
  • Gulf View Townhouses 3
    From $235 per night (USD)

    Expedia

    Gulf View Townhouses 3

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Gulf View Townhouse 3 - Anna Maria Island - 2 Bedroom / 2 1/2 Bath, maximum occupancy of 4 people. VRC16-000063 He ...

    From $235 per night (USD)

    Expedia

    Details
  • Sandy Point Cove 112
    From $165 per night (USD)

    VRBO

    Sandy Point Cove 112

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sandy Point Cove 112 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000138 Distance ...

    From $165 per night (USD)

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    Details
  • LIMEFISH - Stunning Gulf frontage. Secluded private pool. Direct beach and su
    From $1955 per night (USD)

    Expedia

    LIMEFISH - Stunning Gulf frontage. Secluded private pool. Direct beach and su

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    A spectacular, beach front rental on Anna Maria Island, Limefish has magnificent views of the Gulf and is so private you ...

    From $1955 per night (USD)

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    Details
  • Cuddlefish Cove- Beach retreat on Marina Drive.
    From $550 per night (USD)

    VRBO

    Cuddlefish Cove- Beach retreat on Marina Drive.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...

    From $550 per night (USD)

    VRBO

    Details
  • By the Shore: 4  BR, 4  BA House in Holmes Beach, Sleeps 8
    From $754 per night (USD)

    Expedia

    By the Shore: 4 BR, 4 BA House in Holmes Beach, Sleeps 8

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Anna Maria Island's dreamy home with a private, heated pool/spa is just a moment's walk to a sugary white sand beach wit ...

    From $754 per night (USD)

    Expedia

    Details
  • Short Walk to Beaches with Private Heated Pool
    From $427 per night (USD)

    VRBO

    Short Walk to Beaches with Private Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Mermaids Crossing is a newly renovated ground-level home, located just 2 minutes away from the white sandy beaches of th ...

    From $427 per night (USD)

    VRBO

    Details
  • 3011 Ave E-3 in Holmes Beach
    From $175 per night (USD)

    Expedia

    3011 Ave E-3 in Holmes Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    3011 Avenue E, Unit 3 - Triplex Condo 1 Bedroom/ 1 Bath, maximum occupancy of 4 people. VRC16-000051 This tri-plex ...

    From $175 per night (USD)

    Expedia

    Details
  • 313 Island Walk in Holmes Beach
    From $328 per night (USD)

    VRBO

    313 Island Walk in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...

    From $328 per night (USD)

    VRBO

    Details
  • Large Pet Friendly Private Pool Home West of Gulf Dr - Anna Maria
    From $382 per night (USD)

    Expedia

    Large Pet Friendly Private Pool Home West of Gulf Dr - Anna Maria

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Safely enjoy a home-away-from-home vacation here, with the peace of mind that this home is cleaned and up to par with th ...

    From $382 per night (USD)

    Expedia

    Details
  • Anna Maria Island Sunshine Kiss Villa
    From $205 per night (USD)

    VRBO

    Anna Maria Island Sunshine Kiss Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, an ...

    From $205 per night (USD)

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    Details
  • ANNA MARIA ISLAND 5 BEDROOM POOL HOME STEPS TO BEACH
    From $1004 per night (USD)

    Expedia

    ANNA MARIA ISLAND 5 BEDROOM POOL HOME STEPS TO BEACH

    Bedrooms:
    9
    Bathrooms:
    5
    Sleeps:
    10

    Sunset Palms ... This 5 bedroom, 4.5 bath pool home is located just two houses from Anna Maria Island's gorgeous, white ...

    From $1004 per night (USD)

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    Details
  • Anna Maria Island Star FishCondo w/ Boat Slip- -2BR/2BA
    From $225 per night (USD)

    VRBO

    Anna Maria Island "Star Fish"Condo w/ Boat Slip- -2BR/2BA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Starfish Condo on Anna Maria Island -2 BR 2 BA With a 25' Boat Slip Wonderful quiet residential area overlooks pool; bey ...

    From $225 per night (USD)

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    Details
  • Sandy Point Cove 114
    From $196 per night (USD)

    Expedia

    Sandy Point Cove 114

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Sandy Point 114 - Anna Maria Island - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. VRC16-000070 Dis ...

    From $196 per night (USD)

    Expedia

    Details
  • Belle Vue- Relax on your porch and take in the views of the gulf.
    From $891 per night (USD)

    VRBO

    Belle Vue- Relax on your porch and take in the views of the gulf.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Kick off your shoes and promise yourself not to put them on again. Take off your watch and tell time by the location of ...

    From $891 per night (USD)

    VRBO

    Details
  • Silver Surf- A stunning family home 2 blocks from the beach.
    From $1019 per night (USD)

    Expedia

    Silver Surf- A stunning family home 2 blocks from the beach.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...

    From $1019 per night (USD)

    Expedia

    Details
  • For Shore: 5  BR, 4.5  BA House in Holmes Beach, Sleeps 10
    From $814 per night (USD)

    VRBO

    For Shore: 5 BR, 4.5 BA House in Holmes Beach, Sleeps 10

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    If you are hoping to stay on the perfect Old Florida island in the perfect beach home, you have found your destination a ...

    From $814 per night (USD)

    VRBO

    Details
  • GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
    From $330 per night (USD)

    Expedia

    GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...

    From $330 per night (USD)

    Expedia

    Details
  • 510 Bayview in Holmes Beach
    From $744 per night (USD)

    VRBO

    510 Bayview in Holmes Beach

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    6

    510 Bayview - Anna Maria Island - 5 Bedroom / 5 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - ...

    From $744 per night (USD)

    VRBO

    Details
  • Close to Gulf Beaches - Dog Friendly - Private Pool
    From $415 per night (USD)

    Expedia

    Close to Gulf Beaches - Dog Friendly - Private Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Tropic Dream is a ground-level home located in Holmes Beach, just a 2-3 minute stroll to the Gulf! This home includes t ...

    From $415 per night (USD)

    Expedia

    Details
  • Sandy Point  205 in Holmes Beach
    From $163 per night (USD)

    VRBO

    Sandy Point 205 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Distance to t ...

    From $163 per night (USD)

    VRBO

    Details
  • LaPlayita Condo 5 in Holmes Beach
    From $177 per night (USD)

    Expedia

    LaPlayita Condo 5 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC19-000138 Community ...

    From $177 per night (USD)

    Expedia

    Details
  • POOL HOME OPEN FOR THE SUMMER!  BRING YOUR BOAT! MONTH MINIMUM - GREAT PRICE AND A GREAT LOCATION!
    From $166 per night (USD)

    VRBO

    POOL HOME OPEN FOR THE SUMMER! BRING YOUR BOAT! MONTH MINIMUM - GREAT PRICE AND A GREAT LOCATION!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    239 85th Street, Holmes Beach, Anna Maria Island Bailey's Home ... Lovely and spacious 3 bedroom, 2 bath home. Recently ...

    From $166 per night (USD)

    VRBO

    Details
  • My Buoy Blue: 3  BR, 2  BA House in Holmes Beach, Sleeps 6
    From $457 per night (USD)

    Expedia

    My Buoy Blue: 3 BR, 2 BA House in Holmes Beach, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your dream vacation awaits you at My Buoy Blue! On a quiet street and only one block from the beach, this stunning vaca ...

    From $457 per night (USD)

    Expedia

    Details
  • Shell Cottage- Florida style pool home close to beach.
    From $334 per night (USD)

    VRBO

    Shell Cottage- Florida style pool home close to beach.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...

    From $334 per night (USD)

    VRBO

    Details
  • 3011 Ave E-1 in Holmes Beach
    From $281 per night (USD)

    Expedia

    3011 Ave E-1 in Holmes Beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    3011 Avenue E, Unit 1 - Anna Maria Island -Triplex Condo - 4 Bedroom/ 2 Bath, maximum occupancy of 8 people. VRC16-00005 ...

    From $281 per night (USD)

    Expedia

    Details
  • Seaside Beach House 203 Gulf Front Condo  Pool Unforgettable Sunset Views
    From $200 per night (USD)

    VRBO

    Seaside Beach House 203 Gulf Front Condo Pool Unforgettable Sunset Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    VRC20-000296 This property is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high ...

    From $200 per night (USD)

    VRBO

    Details
  • Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
    From $143 per night (USD)

    Expedia

    Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sea La Vie! 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Location! One Block to th ...

    From $143 per night (USD)

    Expedia

    Details
  • Pool Home Located Near Gulf Beaches!
    From $432 per night (USD)

    VRBO

    Pool Home Located Near Gulf Beaches!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...

    From $432 per night (USD)

    VRBO

    Details
  • (2) Bedroom (2) Bath with Private 10' x 30' Sun Deck
    From $350 per night (USD)

    Expedia

    (2) Bedroom (2) Bath with Private 10' x 30' Sun Deck

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre " ...

    From $350 per night (USD)

    Expedia

    Details