Holmes Beach Rentals
From $234 per night (USD)VRBO
Coastal Home with Heated Pool, Close to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Pineapple Palms by Anna Maria Island Accommodations VRC17-000041 Welcome to Pineapple Palms, the ultimate ocean-loving ...
From $234 per night (USD)VRBO
From $426 per night (USD)Expedia
No Bad Days - 1.5 Blocks to Gulf Beaches, Private Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
No Bad Days by Anna Maria Island Accommodations VRC18-000057 Welcome to No Bad Days by Anna Maria Island Accommodatio ...
From $426 per night (USD)Expedia
From $440 per night (USD)VRBO
Holmes Beach Gem! Pool, Grill and Game Room!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Attitude By Latitude by Anna Maria Island Accommodations VRC16-000182 Welcome to Attitude by Latitude, three bedrooms, ...
From $440 per night (USD)VRBO
From $212 per night (USD)Expedia
Heated Pool! Beautiful Condo, Close to Beach - Blue Lagoon 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Blue Lagoon 1 by Anna Maria Island Accommodations VRC16-000166 Welcome to Blue Lagoon 1, a charming vacation condo jus ...
From $212 per night (USD)Expedia
From $284 per night (USD)VRBO
Spacious family home with heated Pool and Spa, Close to Beach! - Shamrock Palms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Shamrock Palms by Anna Maria Island Accommodations VRC16-000106 Welcome to Shamrock Palms, a charming ground level Flo ...
From $284 per night (USD)VRBO
From $399 per night (USD)Expedia
Close to Beach! Home with Putting Green and Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Turtle by Anna Maria Island Accommodations VRC16-000113 Welcome to Sea Turtle, your perfect beach retreat on Anna ...
From $399 per night (USD)Expedia
From $233 per night (USD)VRBO
Beautiful Condo with Pool, Just Steps to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Palms 2 by Anna Maria Island Accommodations VRC16-000099 Welcome to The Palms 2, a beautifully updated second-leve ...
From $233 per night (USD)VRBO
From $251 per night (USD)Expedia
Island Mojo! Family-Friendly Beach Escape!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Mojo by Anna Maria Island Accommodations VRC16-000143 Welcome to Island Mojo, a charming three bedroom, two ba ...
From $251 per night (USD)Expedia
From $308 per night (USD)VRBO
Anna Maria Island Home with Private Pool! - Peach Bellini
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Peach Bellini by Anna Maria Island Accommodations Welcome to Peach Bellini, your perfect island getaway in Holmes Bea ...
From $308 per night (USD)VRBO
From $519 per night (USD)Expedia
6 minutes to Beach! Screened-in and Heated Pool! - Seahorse Cove
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Seahorse Cove by Anna Maria Island Accommodations VRC16-000109 Welcome to Seahorse Cove, a vibrant two-story duplex j ...
From $519 per night (USD)Expedia
From $343 per night (USD)VRBO
Villa with Heated Pool and Swim-up Tiki Bar! Close to Beach - La Mer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
La Mer by Anna Maria Island Accommodations VRC18-000126 Welcome to La Mer, a fabulous beach vacation home just a shor ...
From $343 per night (USD)VRBO
From $599 per night (USD)Expedia
Perfect Vacation Home! Pool, Lounge, and Ping Pong
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Cottage by Anna Maria Island Accommodations VRC16-000159 Welcome to Coconut Cottage, a stunning coastal retrea ...
From $599 per night (USD)Expedia
From $827 per night (USD)VRBO
Canal Front Family Home with Private Dock and Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Jackie’s Cottage by Anna Maria Island Accommodations VRC18-000190 Welcome to Jackie’s Cottage, a stunning one level c ...
From $827 per night (USD)VRBO
From $519 per night (USD)Expedia
Gorgeous Home with a Pool, Outdoor Lounge, and Elevator! Near Beach and Dining
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ohana by Anna Maria Island Accommodations Experience the perfect family vacation at Ohana, a stunning four-bedroom, t ...
From $519 per night (USD)Expedia
From $554 per night (USD)VRBO
Stunning Home with Pool, Tiki Bar, and Game Room! 2 Minute Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Margarita-Ville by Anna Maria Island Accommodations 121 46th Street, Holmes Beach, FL 34217 VRC16-000136 Experience th ...
From $554 per night (USD)VRBO
From $195 per night (USD)Expedia
Beach Home with Pool Access and Private Patio with BBQ Grill! - Little Dream
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Little Dream by Anna Maria Accommodations VRC16-000139 Welcome to Little Dream! A charming one-bedroom, one-bath getaw ...
From $195 per night (USD)Expedia
From $421 per night (USD)VRBO
Beautiful home with pool, elevator, and ping pong table
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beach Retreat by Anna Maria Island Accommodations VRC16-000857 Welcome to Beach Retreat, a bright and spacious four-b ...
From $421 per night (USD)VRBO
From $726 per night (USD)Expedia
Near the Beach with Balconies and Tiki Bar!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Two Pina Coladas by Anna Maria Island Accommodations VRC16-000094 Welcome to Two Pina Coladas by Anna Maria Island Ac ...
From $726 per night (USD)Expedia
From $960 per night (USD)VRBO
Poseidons Palace! Family Fun and Gulf Views!
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 16
Poseidons Palace by Anna Maria Island Accommodations VRC16-000122 Welcome to Poseidons Palace, an extraordinary eight ...
From $960 per night (USD)VRBO
From $841 per night (USD)Expedia
Sea Oats: Anna Maria Island Family Retreat with Pool Just Steps from the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Sea Oats by Anna Maria Island Accommodations VRC16-000115 Welcome to Sea Oats by Anna Maria Island Accommodations, a ...
From $841 per night (USD)Expedia
From $394 per night (USD)VRBO
Vibrant Island Retreat with Pool, Tiki Table and Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ainsley Beach House by Anna Maria Island Accommodations VRC16-000185 Welcome to Ainsley Beach House, a charming three ...
From $394 per night (USD)VRBO
From $321 per night (USD)Expedia
Updated Home with Private Pool! Near Gulf Beaches - Coral Palms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Palms by Anna Maria Island Accommodations VRC16-000157 Welcome to Coral Palms, a beautiful ground level cottage ...
From $321 per night (USD)Expedia
From $343 per night (USD)VRBO
Updated Home, 5 Houses from the Beach! Private Pool and Game Room! - Ocean's 77
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ocean's 77 by Anna Maria Island Accommodations VRC19-000012 Welcome to Ocean's 77, a charming beach cottage just five ...
From $343 per night (USD)VRBO
From $549 per night (USD)Expedia
Beautiful Villa near the Beach with Pool! - Mermaid's Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mermaid's Hideaway by Anna Maria Island Accommodations VRC16-000135 Experience coastal tranquility at Mermaid's Hid ...
From $549 per night (USD)Expedia
From $652 per night (USD)VRBO
Aggie’s Treasure - Perfect family vacation home with private pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Aggie’s Treasure by Anna Maria Island Accommodations VRC16-000187 Experience a true island escape at Aggie’s Treasure ...
From $652 per night (USD)VRBO
From $403 per night (USD)Expedia
Beachfront Balcony, Stylish Gulf-View Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Gables 110 by Anna Maria Vacations VRC16-000126 Welcome to Palm Gables 110, a rare Gulf-front three-bedroom, two ...
From $403 per night (USD)Expedia
From $209 per night (USD)VRBO
Canalfront Cottage Near the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stars on the Water by AMI Locals Duplex in Holmes Beach, Florida VRC21-000115 Perfect for beach and bay lovers alike, ...
From $209 per night (USD)VRBO
From $491 per night (USD)Expedia
Happy Island Cottage: Heated Pool, 5-Min Walk to Beach, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own heated pool, a five-minute walk to the Gulf, and the whole house to yourselves in quiet Holmes Beach on Anna Ma ...
From $491 per night (USD)Expedia
From $526 per night (USD)VRBO
Private Pool - Manna-Tee Beach House by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot fo ...
From $526 per night (USD)VRBO
From $221 per night (USD)Expedia
Beachfront Condominium on the white sandy beach of Anna Maria Island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Sun Plaza West Beachfront Condominiums. This complex is ON the beach. It doesn’t get better than that. This b ...
From $221 per night (USD)Expedia
From $521 per night (USD)VRBO
GULF FRONT Beautiful Condo, Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two-bedroom, two-bath u ...
From $521 per night (USD)VRBO
From $358 per night (USD)VRBO
Buddy’s Beach House Private Heated Pool and Spa- Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Buddy's Beach House, a completely remodeled, beachy chic getaway just 2 blocks to the beach. Stroll to the be ...
From $358 per night (USD)VRBO
From $361 per night (USD)VRBO
Fun family vacation home, just one block to the AMI beach. You'll love the pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Pineapple by AMI Locals CAA20-000023 Welcome to Blue Pineapple by AMI Locals, a stylish 4-bedroom, 2.5-bathroom ...
From $361 per night (USD)VRBO
From $295 per night (USD)VRBO
Steps to Beach - Tropical Sunset 1 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently ...
From $295 per night (USD)VRBO
From $424 per night (USD)VRBO
Pool, Spa, Mini Golf, Games, Beach, sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to our updated 2-bed, 2-bath condo on Anna Maria Island! Perfect for 6 guests, this tropical retreat features a s ...
From $424 per night (USD)VRBO
From $361 per night (USD)Expedia
Home with heated pool, spa, games, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this modern 2BR/2BA beachside retreat on Anna Maria Island. Enjoy a sunlit open-concept living area with coast ...
From $361 per night (USD)Expedia
From $411 per night (USD)VRBO
Coconuts 116 - Anna Maria Island - Condo -1 Bedroom/ 1 Bath- maximum occupancy of 6 people. Distance to the Beach: 3 min walk Community pool.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts 116 - Anna Maria Island - 1 Bedroom/ 1 Bath - maximum occupancy of 6 people. Vrc21-000194 Distance to the Beac ...
From $411 per night (USD)VRBO
From $417 per night (USD)Expedia
Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fins Up! On Anna Maria Island (Holmes Beach, FL) The Space Your serene island retreat where simplicity meets ...
From $417 per night (USD)Expedia
From $158 per night (USD)VRBO
Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cabin 1 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #1, Holmes Beach, FL 34217 What You'll Lov ...
From $158 per night (USD)VRBO
From $428 per night (USD)Expedia
Anna Maria Island!1 Block to the Beach. Private Home with Heated Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the ultimate luxury of this beautiful private home just minutes from the white private sandy beaches of Anna ...
From $428 per night (USD)Expedia
From $309 per night (USD)VRBO
Perfect Vacation Home with Private Pool! Close to the Beach! - Gulf Breeze
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Breeze by AMI Locals VRC21-000001 Welcome to Gulf Breeze, a charming three bedroom, two bath home just a short f ...
From $309 per night (USD)VRBO
From $302 per night (USD)Expedia
Charming Island Pool Home! Walk to Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze by AMI Locals VRC21-000002 Welcome to Sea Breeze by AMI Locals, a charming three-bedroom, two-bathroom coa ...
From $302 per night (USD)Expedia
From $255 per night (USD)VRBO
Cozy Home with Private Pool, Close to the Beach! Don't Miss Out!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Escape by AMI Locals VRC21-000012 Welcome to Island Escape, a charming vacation home featuring a private pool ...
From $255 per night (USD)VRBO
From $643 per night (USD)Expedia
Golf cart Inc + 4bd/2bth + private pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recent Review: "This is an incredible place to stay. The location is awesome, the communication is phenomenal and the ho ...
From $643 per night (USD)Expedia
From $230 per night (USD)VRBO
Gulf Beach Apartment - with Pool & Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pristine,spacious1 bedroom apartment sleeps 4, only steps to the beautiful white sandy beach of Anna Marie Island. Fresh ...
From $230 per night (USD)VRBO
Click For PricingVRBO
Work, Play or Vacation in paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Tortuga Tides, your perfect beach retreat just a short stroll from the world-famous sugar-white sands and tur ...
Click For PricingVRBO
From $225 per night (USD)VRBO
Charming 2bed AMI Beach Cottage 1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our remodeled 2beds/1bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Anna Mari ...
From $225 per night (USD)VRBO
From $282 per night (USD)Expedia
Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/1bath 1/2 of the duplex, UNIT A - just short walk (3-5min)to the white sandy beach ...
From $282 per night (USD)Expedia
From $1312 per night (USD)VRBO
Surfside AMI; backyard oasis steps to beach, heated pool, putting green,+gear!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Recently renovated in 2025, new kitchen, flooring and updated furnishings! Private beach getaway with a backyard oasis i ...
From $1312 per night (USD)VRBO
From $481 per night (USD)Expedia
Island Haven by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for a great vacation location on beautiful Holmes Beach? Then look no further. Island Haven is a two-story, priv ...
From $481 per night (USD)Expedia
From $354 per night (USD)VRBO
Emerald Cove: Beachfront condo with gorgeous views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come soak in the picturesque gulf views of Anna Maria Island at this newly renovated, contemporary beach condo! This 1 b ...
From $354 per night (USD)VRBO
From $244 per night (USD)Expedia
Perfect Family Vacation home just off the beach! Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Hideaway by AMI Locals VRC21-000085 Escape to Island Hideaway, a charming one-bedroom, one-bath home perfectly ...
From $244 per night (USD)Expedia
From $435 per night (USD)VRBO
Sun Plaza West Unit 204, gulf front complex on Ami
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Vrc19-000080 Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2-bedroom 2-bathroom Condo ...
From $435 per night (USD)VRBO
From $349 per night (USD)Expedia
Recently Renovated Luxury Ground Floor Island Home Close to Beach!o Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Limbo Cottage - the west side of 'Gumbo Limbo' duplex. Located just 7 houses from the Gulf beaches of Anna Ma ...
From $349 per night (USD)Expedia
From $726 per night (USD)VRBO
CONTEMPORARY BEACH CHIC HOME WITH OCEAN VIEWS, STEPS TO THE BEACH/HEATED POOL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
THE POOL IS PRIVATE AND ONLY FOR THE USE OF THE GUESTS IN THIS HOME WHICH IS SEABREEZE SANDS. IT IS NOT SHARED WITH ANY ...
From $726 per night (USD)VRBO
From $305 per night (USD)VRBO
Old Florida living only 200 steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Paradise found! With only 200 steps to the beach, this lovely beach house offers a great value for you vacation. A sho ...
From $305 per night (USD)VRBO
From $364 per night (USD)VRBO
Pool/Spa - Bahama Mama by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is it - Paradise! This fabulous Key West style elevated 3 bedroom/2 bath single family home has so many wonderful f ...
From $364 per night (USD)VRBO
From $403 per night (USD)Expedia
Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Calypso" is a Newly remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall, ...
From $403 per night (USD)Expedia
From $371 per night (USD)VRBO
Palms Beach West - Holmes Beach Vacation Villa - 3 Bedroom with Private Pool - B
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories that last a lifetime when you stay at gorgeous Anna Maria Island vacation rental home “Palms Beach West”. ...
From $371 per night (USD)VRBO
From $161 per night (USD)VRBO
Sandy Pointe II Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This is a light and bright 2 bedroom/2 bath Condo that backs up to the lovely and serene mangroves (nature preserve). T ...
From $161 per night (USD)VRBO
From $221 per night (USD)VRBO
STEPS TO GULF BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Authentic ground floor Bungalow with private parking and seashell courtyard just steps away from the Gulf Beaches. Cozy ...
From $221 per night (USD)VRBO
From $675 per night (USD)VRBO
Direct Beachfront 2 BD Condo On Florida’s Beautiful Gulf Coast!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Florida Vacation Dream Spot - easy and fun! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up a ...
From $675 per night (USD)VRBO
From $288 per night (USD)VRBO
Coastal Condo, Heated Pool Steps from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Short walk to the beautiful beaches of Holmes Beach • Heated community pool with lounge chairs a ...
From $288 per night (USD)VRBO
From $224 per night (USD)Expedia
Pet-Friendly - Rum Dog by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath dup ...
From $224 per night (USD)Expedia
From $378 per night (USD)VRBO
One Day More: Spectacular Oasis Backyard with Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
403 72nd St., Holmes Beach, FL 34217 What You'll Love About this Home: Location! 4 Blocks to the Beach! Centrally Locat ...
From $378 per night (USD)VRBO
Click For PricingExpedia
Beautiful AMI Beach House with Pool and Fenced Backyard, Dog Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sol y Mar by AMI Locals VRC21-000118 Welcome to Sol y Mar, a bright and newly refreshed three-bedroom beach house oasi ...
Click For PricingExpedia
From $236 per night (USD)VRBO
END OF SUMMER SPECIAL- Private patio-Central location & trolley-3min to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This is a fabulously styled cottage is set back 30 yards from the Gulf ocean (one house off the beach as the crow flies) ...
From $236 per night (USD)VRBO
From $216 per night (USD)VRBO
END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this boutique-styled cottage and the white sandy beaches that make Anna Maria Island so famous. The Cottage is ...
From $216 per night (USD)VRBO
From $622 per night (USD)VRBO
One Bedroom Condo at Beachfront Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Courtyard! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $622 per night (USD)VRBO
From $637 per night (USD)Expedia
Unwind Sunshine - heated pool, steps to the local's favorite beach, free bikes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
***WEEKLY RENTAL**** This Luxury beach chic cottage home has it all....location, fully stocked luxury kitchen, and beac ...
From $637 per night (USD)Expedia
From $535 per night (USD)VRBO
Anna Maria Island Beachfront Rental | Gulf Place 22 | 2BR/2BA | heated pool, tennis court, trolley access, sleeps 6.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Experience the ultimate Anna Maria Island beachfront vacation at Gulf Place Unit 22, a b ...
From $535 per night (USD)VRBO
From $492 per night (USD)Expedia
Catchin' Rays-150 yards to the Beach-By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
“Catchin’ Rays” is an excellent choice for your next Anna Maria Island vacation! This centrally located home offers ever ...
From $492 per night (USD)Expedia
From $241 per night (USD)VRBO
Sam's Cove! Second Floor Condo Overlooking Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
IMPORTANT: Per homeowner's association, a minimum monthly stay is required, as well as an application. Please allow at l ...
From $241 per night (USD)VRBO
From $214 per night (USD)Expedia
Made in Shade A · Beach Across St · Pets OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC22-000010 1BR · 1BA · Sleeps 4 · Beach Across the Street · 1-Min Walk to Gulf · Pet-Friendly (With Approval) · Priva ...
From $214 per night (USD)Expedia
From $214 per night (USD)VRBO
Made in Shade B · Beach Across St · Pets OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC22-000022 1BR · 1BA · Sleeps 4 · Beach Across the Street · 1-Min Walk to Gulf · Pet-Friendly (With Approval) · Priva ...
From $214 per night (USD)VRBO
From $320 per night (USD)Expedia
Charming Ground Level Resort Style 3unit condo unit B a few steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly updated ground level 2 beds/2bath unit B of the triplex located on the southern end of Holmes Beach ...
From $320 per night (USD)Expedia
From $422 per night (USD)VRBO
Sea Breeze: Pool home in perfect central location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bed 2 bath island oasis will take you back to the days of old Florida charm, but in a modern and well appointed s ...
From $422 per night (USD)VRBO
From $422 per night (USD)Expedia
Getaway Retreat A · Firepit · 1 Block to Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2BR · 2BA · Sleeps 6 · Pet-Friendly ($150 Fee) · 1 Block to Bay · Kayak Launch · Firepit & Gas Grill · Private Sundeck · ...
From $422 per night (USD)Expedia
From $422 per night (USD)VRBO
Getaway Retreat B · Firepit · 1 Block to Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2BR · 2BA · Sleeps 6 · Pet-Friendly ($150 Fee) · 1 Block to Bay · Kayak Launch · Firepit & Gas Grill · Private Sundeck · ...
From $422 per night (USD)VRBO
From $308 per night (USD)Expedia
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly updated ground level 2 beds/2bath unit A of the triplex located on the southern end of Holmes Beach ...
From $308 per night (USD)Expedia
From $266 per night (USD)VRBO
Steps to Beach - SunSet Azul by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunset Azul is a fully-updated 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. It's ...
From $266 per night (USD)VRBO
From $509 per night (USD)VRBO
Putting Green - Flip Flops Forever by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet resi ...
From $509 per night (USD)VRBO
From $222 per night (USD)VRBO
Private 2 bedroom, 2 bath ground level cottage west of Gulf Drive!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This colorful, recently updated 2-bedroom, 1.5-bathroom ground level home is delightfully placed just a block and a half ...
From $222 per night (USD)VRBO
From $231 per night (USD)Expedia
2 bedroom unit, West of Gulf Drive. Only steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome! This quaint 2-bedroom, 1-bathroom single level home is nestled on Anna Maria Island. The master suite has a ...
From $231 per night (USD)Expedia
From $257 per night (USD)VRBO
Delightful, comfortable villa just steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Placed in the heart of Anna Maria Island, this wonderful, single story, fully furnished 2-bedroom, 2-bathroom home is ne ...
From $257 per night (USD)VRBO
From $426 per night (USD)Expedia
Gulf-front, heated pool, stocked kitchen, and private parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A beautiful, beachfront condo has 2 bedrooms and 2 bathrooms and a gorgeous balcony view of the Gulf of Mexico. The smal ...
From $426 per night (USD)Expedia
From $486 per night (USD)VRBO
Cozy Night Side Cottage, 2 BR, Heated Pool on quiet street on Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC# 19-000219 This cozy 2 bedroom 2 full bath cottage is half of our A Lazy River Day and Night duplex. You will feel ...
From $486 per night (USD)VRBO
From $209 per night (USD)Expedia
Seabreeze B · Pet-Friendly · Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000531 2BR · 2BA · Sleeps 6 · Pet-Friendly · Shared Heated Pool · Private Decks · Landscaped Picnic Area · Charco ...
From $209 per night (USD)Expedia
From $430 per night (USD)VRBO
Four Beach Lovers 2 · Gulf Front · Solar Powered · Steps to Sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC16-000516 1BR · 1BA · Sleeps 4 · Direct Gulf Front · Private Patio · 2025 Renovation · King Bed · Wine Fridge · Beac ...
From $430 per night (USD)VRBO
From $517 per night (USD)Expedia
Sapphire Beach House by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casual yet luxurious, this three-bedroom duplex with a private, heated pool and close proximity to the beach is the perf ...
From $517 per night (USD)Expedia
From $293 per night (USD)VRBO
Gulf Shores Beachfront Condo Gorgeous views and only steps to the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
View dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out t ...
From $293 per night (USD)VRBO
From $191 per night (USD)Expedia
WBC 223 Beautiful 2/2 Remodeled Close to Beach, Tennis, 2 Heated Pools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC21-000082 West Bay Cove 223 located at 600 Manatee is a picturesque and luxurious two bedroom two bath condo which ...
From $191 per night (USD)Expedia
From $391 per night (USD)VRBO
Ideal Family Getaway: Private Pool 2 Mins from the Beach - Lay'By, Too
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lay'By, Too by AMI Locals VPR16-000175 Welcome to Lay'By, Too, a vibrant ground-level vacation home just four house ...
From $391 per night (USD)VRBO
From $416 per night (USD)Expedia
Sailfish Gulf Suites #2, Beachfront, Steps to the Sand
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable ...
From $416 per night (USD)Expedia
From $406 per night (USD)VRBO
2 Bedroom Townhouse for Unforgettable Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to La Playita #2 a spacious 2 bedroom, 2 bath townhouse in a small quiet complex just 1 block to the beach. � ...
From $406 per night (USD)VRBO
From $762 per night (USD)Expedia
A Lazy River Day & Night 4 Bedrm w lazy river heated pool! Bikes & Beach Gear!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VRC# 19-000218 VRC# 19-000219 You just found your slice of Paradise! Versatile 4 bedroom 3 1/2 bath home perfect for f ...
From $762 per night (USD)Expedia
From $244 per night (USD)VRBO
Palm Cay 3 · 3 Queen Beds · 2-Min Walk to Gulf
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000554 2BR · 1BA · Sleeps 6 · 3 Queen Beds · Less Than 2-Min Walk to Gulf · Heated Pool · Coin Laundry On-Site · ...
From $244 per night (USD)VRBO
From $263 per night (USD)Expedia
Ocean Park Terrace 202 · Ocean Park 202 · Rooftop Deck · 1-Month Min
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
2BR · 2BA · Sleeps 5 · Direct Gulf Front · Private Rooftop Deck · Spiral Staircase · Gulf & Intracoastal Views · Wet Bar ...
From $263 per night (USD)Expedia
From $497 per night (USD)VRBO
Franks Beach House · Gulf Front · Bose Sound
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000543 3BR · 2BA · Sleeps 6 · Direct Gulf Front · Large Open Deck · Screened Lanai · Bose Sound System · Granite ...
From $497 per night (USD)VRBO
From $321 per night (USD)Expedia
While Away A · EV Charger · Fenced Pool · Renovated 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000510 2BR · 2BA · Sleeps 6 · Private Fenced Heated Pool · EV Charger Included · Master with Direct Pool Access · ...
From $321 per night (USD)Expedia