Holmes Beach Rentals
From $213 per night (USD)VRBO
Mermaid Retreat: Fantastic Location STEPS to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Mermaid's Retreat by Anna Maria Island Accommodations 104 29th St Unit 3, Holmes Beach, FL 34217 Highlights: • Locat ...
From $213 per night (USD)VRBO
From $885 per night (USD)VRBO
**NEW** -Spa, Pool Table, PuttPutt, Near Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the heart of Holmes Beach, Florida, this beautiful 4-bedroom, 5.5 bath home is the ultimate costal retreat. ...
From $885 per night (USD)VRBO
From $396 per night (USD)VRBO
Beachfront Home, Heated Pool on AMI by Gulfcoast Holiday Homes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two-story townhome on Anna Maria Island, just a 2 minute walk from the pristine white sand beach. Enjoy a private pool, ...
From $396 per night (USD)VRBO
From $514 per night (USD)Expedia
~ WE ARE OPEN ~ BEACHFRONT ~ YES THAT'S YOUR VIEW! ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to announce that our Coconuts beachfront condo is open! We didn't have any damage to our unit from the re ...
From $514 per night (USD)Expedia
From $358 per night (USD)VRBO
APRIL AND MAY HAS AVAILABILITY! THIS BEACH CONDO HAS A 14 NIGHT MINIMUM STAY!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The sparkling, blue waters of the Gulf of Mexico await you at 105 Tiffany Place. Located directly on Anna Maria Island's ...
From $358 per night (USD)VRBO
From $130 per night (USD)VRBO
2B/2B on Anna Maria Island 3 blocks from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Clean, cheerful, updated and renovated family home. Tile floors throughout. Front porch, and back porch. Two blocks in b ...
From $130 per night (USD)VRBO
From $297 per night (USD)VRBO
Beautiful Condo on Anna Marie Island at Tiffany Place
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This well appointed condo on Anna Maria is ready for rent! Everything you need is here for you. Pack some clothes and c ...
From $297 per night (USD)VRBO
From $678 per night (USD)Expedia
Chasing Sunsets managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
~ CHASING SUNSETS ~ At A Glance: Stunning 4 bedroom and 3 bathroom home 2 king bedrooms, 1 queen and one bunk bed ...
From $678 per night (USD)Expedia
From $315 per night (USD)VRBO
Sandy Point Cove 202 - Anna Maria Island -Condo 2 Bedroom/ 2 Bath, maximum...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Point Cove 202 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC16-000538 D ...
From $315 per night (USD)VRBO
From $325 per night (USD)VRBO
Island Vibe 2: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Rent with attached duplex Island Vibe 3 (VRBO# 1307973) if you need 5 bedrooms! Welcome to Island Vibe 2, a renovated 3 ...
From $325 per night (USD)VRBO
From $517 per night (USD)VRBO
AMI Tropical Oasis - A private house very close to the beach on a great street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This completely custom remodeled island 3 bedroom 2 bath 2200 sq ft. pet friendly home with a fantastic back yard. It i ...
From $517 per night (USD)VRBO
From $170 per night (USD)VRBO
Sandy Point get away on AMI excellent location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet location, removed from the street, turn down the drive & crossover wooden bridge and arrive at Sandy Pointe Condom ...
From $170 per night (USD)VRBO
From $631 per night (USD)VRBO
TOES IN THE SAND! GULF FRONT HOME WITH HEATED POOL, GORGEOUS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
IN THE EVENT OF A MANDATORY EVACUATION DUE TO A STORM/HURRICANE GUESTS WILL RECEIVE A FULL REFUND. Waves Edge South is ...
From $631 per night (USD)VRBO
From $475 per night (USD)VRBO
Family Friendly Anna Maria Island Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VRC19-000271-0* Calendar does NOT reflect availability- --contact me for minimum requirement. VRBO website does NOT det ...
From $475 per night (USD)VRBO
From $819 per night (USD)VRBO
Beachfront Condo with Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located on beautiful Anna Maria Island, La Plage 10 is one of only six units on the Island that have a full beachfront v ...
From $819 per night (USD)VRBO
From $585 per night (USD)VRBO
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Address of Areca Cove: 206 N Harbor Drive, Holmes Beach, FL 34217 beautifulannamaria@yahoo.com ARECA COVE - A bright an ...
From $585 per night (USD)VRBO
From $271 per night (USD)VRBO
Beach Place... An island treasure. Not available due to hurricane
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You can walk or bike to beach, restaurants, shopping and more. 2 blocks to beach. Perfect area. Need no CAR. Beautiful ...
From $271 per night (USD)VRBO
From $621 per night (USD)Expedia
Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
JULY 4TH WEEK OPEN AND PRICE JUST REDUCED! WE ARE OPEN FOR RENTERS AFTER THE STORMS. POOL IS OPEN AS WELL! Sunset Land ...
From $621 per night (USD)Expedia
From $237 per night (USD)VRBO
Across the street from the Beach, restaurants, free wifi.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience an Anna Maria Island getaway with this stunning vacation rental just steps away from the Gulf of Mexico. Nest ...
From $237 per night (USD)VRBO
From $431 per night (USD)Expedia
Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block to beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coastal cottage located 1 block from fabulous white sands of holmes beach. Stay in comfort in our spacious 3 bedroom 2 b ...
From $431 per night (USD)Expedia
From $329 per night (USD)VRBO
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrill ...
From $329 per night (USD)VRBO
From $362 per night (USD)VRBO
Anna Maria Rental Steps to Gulf Beach with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2000 square foot home on beautiful Anna Maria Island Florida, with all the upgrades and amenities. Short two block walk ...
From $362 per night (USD)VRBO
From $246 per night (USD)VRBO
Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This complex at 7100 Gulf Drive is well managed, impeccably maintained and has a reputation of being one of the island's ...
From $246 per night (USD)VRBO
From $280 per night (USD)VRBO
Happy, Beachy Holmes Beach Condo Tennis, Heated Pool, Elevator Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just Bring You to this beautifully appointed bright beach condo - freshly painted Jan 2022 with brand new plank flooring ...
From $280 per night (USD)VRBO
From $324 per night (USD)VRBO
Gorgeous Home Just Steps to Beach, Miles of White Sandy Beach ST lic DWE5105216
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous home is just steps to the beach, with other beautiful homes nearby. This beautiful home is one of two, wit ...
From $324 per night (USD)VRBO
From $320 per night (USD)Expedia
Quaint & Cozy Beachside Apartment - 75 Steps to Beach - Bamboo Apts. #4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Bamboo Apartments, Apartment #4, part of our family-owned five-unit beachfront retreat featured in Southern L ...
From $320 per night (USD)Expedia
From $285 per night (USD)VRBO
Tropical Paradise Cottage on the Beach VRC17-000167
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This quaint cottage is located "on the beach" - 3007 Avenue F Unit 3 at 30th Street on beautiful Holmes Beach. It is th ...
From $285 per night (USD)VRBO
From $605 per night (USD)VRBO
Gulf Place Condominium, Unit #13
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Book your next Anna Maria Island Vacation at this popular gulf front complex. This relaxing condominium unit consists of ...
From $605 per night (USD)VRBO
From $224 per night (USD)VRBO
Tranquil AMI Resort Unit 2 all amenities! Central Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...
From $224 per night (USD)VRBO
From $539 per night (USD)VRBO
White Sands Beach House -Luxury home, heated pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beachy, four-bedroom, three-bath vacation rental is located in the middle of Anna Maria Island. We are 1 1/2 bloc ...
From $539 per night (USD)VRBO
From $496 per night (USD)VRBO
Wish Upon a Starfish by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Wish Upon a Starfish, where all your island dreams come true! This elevated Key West style 3 bedroom home is truly par ...
From $496 per night (USD)VRBO
From $664 per night (USD)Expedia
Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Relax in this comfy, coastal home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach Hous ...
From $664 per night (USD)Expedia
From $364 per night (USD)VRBO
Your Island Oasis in Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Less than a block to white avenue beach nestled in a highly desirable neighborhood in Holmes beach, this wonderful 2 bed ...
From $364 per night (USD)VRBO
From $337 per night (USD)Expedia
Chasing Waves managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC21-000089 107 78th street Holmes Beach 34217 “You are vacationing in a residential area. Please be a good neighbor b ...
From $337 per night (USD)Expedia
From $813 per night (USD)VRBO
Slice of Paradise managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Slice of Paradise VRC21-000047 216 68th St - Holmes Beach - FL - 34217 This stunning custom built and decorated 4 bedroo ...
From $813 per night (USD)VRBO
From $615 per night (USD)Expedia
Groovy Guava by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Groovy Guava! This 2 bed/2 bath villa features a private, heated pool less than 1 block from the powder white ...
From $615 per night (USD)Expedia
From $522 per night (USD)VRBO
Beach Daze by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach Daze! This 2 bed/2 bath villa features a private, heated pool less than 1 block from the powder white b ...
From $522 per night (USD)VRBO
From $395 per night (USD)Expedia
Key Lime Cottage by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Key Lime Cottage! This 2 bed/2 bath cottage has completed a stunning remodel. Brand new tile floors, kitchen, ...
From $395 per night (USD)Expedia
From $191 per night (USD)VRBO
Gulf Beach Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This cute spacious beach bungalow is arguably one of the best values on the island for immediate beach access located at ...
From $191 per night (USD)VRBO
From $449 per night (USD)VRBO
Beach Oasis! Beachfront Condo with Unforgettable Sunsets, Heated Pool, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Forget everything around you and switch to vacation mode the moment you step foot onto this beachfront balcony. Located ...
From $449 per night (USD)VRBO
From $379 per night (USD)VRBO
Private Pool - Misty Beach by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of Holmes Beach on Anna Maria Island rests this charming pet-friendly home just steps to the beaches. Misty ...
From $379 per night (USD)VRBO
From $514 per night (USD)Expedia
Resting Beach Place managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
5608 GULF DR UNIT 111 SUN PLAZA WEST, HOLMES BEACH, FL 34217 VRC19-000241 Book with confidence: Cancellations up to 30 ...
From $514 per night (USD)Expedia
From $522 per night (USD)VRBO
Azure Beach House hosted by Beach Retreats FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000317 304 60th St Unit A Holmes Beach FL 34217 Escape to Azure Beach House—a stunning 3-bedroom, 2-bathroom vaca ...
From $522 per night (USD)VRBO
From $1160 per night (USD)Expedia
UNFORGETTABLE BEACH HOME! Heated pool/spa! Just steps to beach & Stunning views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly located on Holmes Beach, AMI. Just steps to the beach! This beautifully built (2021) home sets the highest st ...
From $1160 per night (USD)Expedia
From $320 per night (USD)VRBO
Pool - Casa Del Mar by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Del Mar is a beautiful Key West-style home featuring 4 bedrooms/2.5 bathrooms. This property is located on the nort ...
From $320 per night (USD)VRBO
From $500 per night (USD)Expedia
Our Waterfront Home Is All Ready Just For You!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a v ...
From $500 per night (USD)Expedia
From $793 per night (USD)VRBO
Steps to Beach! New Post-Helene Video
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Ah, the smell of salt and sand. There's no elixir on this blessed earth like it. Our luxury Anna Maria Island Townhome ...
From $793 per night (USD)VRBO
From $572 per night (USD)Expedia
Waters Edge 110N by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Water's Edge, a beachfront getaway with stunning views! The Water's Edge 110N condo is a beautiful two-bedroo ...
From $572 per night (USD)Expedia
From $962 per night (USD)VRBO
Just Beachy managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
128 49th St Holmes Beach VRC 21-000019 You may cancel your reservation up to 60 days before check-in for a full refund m ...
From $962 per night (USD)VRBO
From $198 per night (USD)VRBO
Escape to Paradise, visit Anna Maria Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Anna Maria Island is one of Florida's most beautiful islands. Out of the way, yet easily accessible. Incredible Sunsets ...
From $198 per night (USD)VRBO
From $463 per night (USD)VRBO
Charming Home on Anna Maria Island 2 Blocks from Beach with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3 bedroom, 2 bathroom, split floor plan on the North end of Holmes Beach, Anna Maria Island. This home is ever ...
From $463 per night (USD)VRBO
From $392 per night (USD)Expedia
Gone Coastal Too by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Announcement* Please note that for all bookings with arrival between now and September 2025 the guest bedroom will hav ...
From $392 per night (USD)Expedia
From $713 per night (USD)VRBO
Gone Coastal Duplex by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*Announcement* Please note that for all bookings with arrival between now and September 2025 the fourth bedroom will hav ...
From $713 per night (USD)VRBO
From $421 per night (USD)Expedia
PRIVATE HEATED POOL! 150 Steps to Beach! No property management fees!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Gulf Breeze is a cozy Key West style coastal cottage ideally located 150 steps to the beautiful white sand beach. The p ...
From $421 per night (USD)Expedia
From $516 per night (USD)VRBO
The Pink Chicken by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Pink Chicken! A beautifully updated and bright 3 bedroom home on Anna Maria Island. *Features include* ...
From $516 per night (USD)VRBO
From $543 per night (USD)Expedia
Gone Coastal 3 by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This stylish 3 bedroom, 2 and a half bath vacation home is located just a short walk from Anna Maria Island's sugar whit ...
From $543 per night (USD)Expedia
From $401 per night (USD)VRBO
Gone Coastal by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Gone Coastal, where every detail was carefully crafted for an unforgettable stay. *Features include* * Pri ...
From $401 per night (USD)VRBO
From $462 per night (USD)Expedia
Spend your AMI vacation at Our Blue Heaven!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our Paradise Regained! After months of hard work, the reconstruction after significant damage caused by hurricanes Helen ...
From $462 per night (USD)Expedia
From $405 per night (USD)VRBO
WE 110 Lovely Gulf Front 2/2 Pool Condo Relax On Sugar Sand Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC 22-000004 Waters Edge Condo 110S is a gorgeous two bedroom, two bath direct Gulf front unit, located at 5806 Gulf D ...
From $405 per night (USD)VRBO
From $524 per night (USD)Expedia
A Lazy River Day & Night 4 Bedrm w lazy river heated pool! Bikes & Beach Gear!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
VRC# 19-000218 VRC# 19-000219 Versatile 4 bedroom 3 1/2 bath home perfect for families or friends traveling together b ...
From $524 per night (USD)Expedia
From $415 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 $415 per night (USD)VRBO
From $380 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 $380 per night (USD)VRBO
From $242 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 $242 per night (USD)VRBO
From $620 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 $620 per night (USD)Expedia
From $207 per night (USD)VRBO
NEW SUMMER RATES! Private patio-Close to everything & trolley-3min walk 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 $207 per night (USD)VRBO
From $204 per night (USD)VRBO
SUMMER RATES! Cozy cottage close to everything-Private patio-3 min to the 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 $204 per night (USD)VRBO
From $194 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 $194 per night (USD)VRBO
From $519 per night (USD)Expedia
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 $519 per night (USD)Expedia
From $366 per night (USD)VRBO
Sandcastle by the Sea managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
213 76th St. Bradenton Beach, Fl 34217 VRC21-000119 “You are vacationing in a residential area. Please be a good neighb ...
From $366 per night (USD)VRBO
From $143 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 $143 per night (USD)VRBO
From $269 per night (USD)VRBO
Island Vibe 6: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rent with attached duplex Island Vibe 5 (VRBO# 1919652) if you need 4 bedrooms! Welcome to Island Vibe 6, a newly renov ...
From $269 per night (USD)VRBO
From $313 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 $313 per night (USD)VRBO
From $343 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 $343 per night (USD)VRBO
From $353 per night (USD)Expedia
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 $353 per night (USD)Expedia
From $564 per night (USD)VRBO
CONTEMPORARY BEACH CHIC HOME WITH OCEAN VIEWS, STEPS TO THE BEACH/HEATED POOL\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
In the heart of Holmes Beach, this lovely three-bedroom house offers a perfect blend of sunshine, sandy beaches, and oce ...
From $564 per night (USD)VRBO
From $262 per night (USD)VRBO
Your island destination steps from the beach!<br>
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tortuga tides is your extended vacation oasis steps from the white sands of Anna Maria Island beaches. The master bedroo ...
From $262 per night (USD)VRBO
From $994 per night (USD)VRBO
Surfside AMI; backyard oasis steps to beach, heated pool, putting green,+gear!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Recently renovated in 2025, new kitchen, flooring and updated furnishings! Private beach getaway with a backyard oasis i ...
From $994 per night (USD)VRBO
From $633 per night (USD)Expedia
Calico AMI – Steps to Sand, Family Paradise!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Are you dreaming of mornings by the pool and evenings watching sunsets on the sand? Are you travelling with little ones ...
From $633 per night (USD)Expedia
From $297 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 $297 per night (USD)VRBO
From $266 per night (USD)VRBO
Island Vibe 5: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rent with attached duplex Island Vibe 6 (VRBO# 1930033) if you need 4 bedrooms! Welcome to Island Vibe 5, a newly renov ...
From $266 per night (USD)VRBO
From $493 per night (USD)VRBO
Private paradise w/ all the beach supplies & toys!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Laguna is a privately owned home with private amenities and entry via smart locks. The home is surrounded by lush ...
From $493 per night (USD)VRBO
From $743 per night (USD)Expedia
PRIVATE HOUSE and Pool on AMI. Close to beach, shopping, restaurants, marina.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SALTY DOGS ON ANNA MARIA ISLAND IS WAITING FOR YOU! SALTY DOGS IS A SINGLE-FAMILY BEACH HOUSE. You get the entire h ...
From $743 per night (USD)Expedia
From $355 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 $355 per night (USD)VRBO
From $381 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 $381 per night (USD)VRBO
From $288 per night (USD)VRBO
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 $288 per night (USD)VRBO
From $753 per night (USD)VRBO
Water Front/Heated Pool/Dock/Walk To Beach/Self Check In-Out/High cleaning/WiFi.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama ...
From $753 per night (USD)VRBO
From $289 per night (USD)VRBO
Coastal Chic Waterfront Condo Anna Maria Island Westbay Point 195 Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the charm of Anna Maria Island and its relaxed coastal lifestyle, just minutes from the beach. Enjoy fishing, ...
From $289 per night (USD)VRBO
From $334 per night (USD)Expedia
★ Spacious Condo ★ Steps to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Very private! Spacious 2 bedroom 2 full bath condo is just steps to Holmes Beach beach. Ocean view from your unit with t ...
From $334 per night (USD)Expedia
From $753 per night (USD)VRBO
Beach Dance in Holmes Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Beach Dance is the perfect family home in a convenient location just steps to the Gulf, Restaurants, Shops and the Free ...
From $753 per night (USD)VRBO
From $399 per night (USD)Expedia
Relax & Unwind at Bryant’s Beach Bungalow!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your getaway is only 400 steps from the beautiful beach! This spacious three-story home is designed for comfort, conveni ...
From $399 per night (USD)Expedia
From $529 per night (USD)VRBO
Kickback Cabana managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
411 79th Street Holmes Beach, Fl 34217 VRC19-000189 You may cancel your reservation up to 60 days before check-in for a ...
From $529 per night (USD)VRBO
From $353 per night (USD)Expedia
Sandy Cheeks & Barefeet, Gorgeous Gulf beach Place, Summer\nspecials
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf views from several rooms and lanai! Quick access (only 1 small house between you and sun & sand). 2 Bedroom, 2 Bath ...
From $353 per night (USD)Expedia
From $321 per night (USD)VRBO
View of Beach from the deck, Walk to all , free WIFI.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the ultimate Anna Maria Island getaway with this charming vacation rental just minutes away from th ...
From $321 per night (USD)VRBO
From $335 per night (USD)Expedia
Beachfront Bliss at Bamboo Apartments #2– A Hidden Gem on Anna Maria Island!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hello, Guest! Welcome to Bamboo Apartments, Apartment #2, part of our family-owned five-unit beachfront retreat featur ...
From $335 per night (USD)Expedia
From $512 per night (USD)VRBO
Caribbean Surf managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
306 67th Street Unit B Holmes Beach, FL 34217 VRC 19-000277 You may cancel your reservation up to 60 days before check-i ...
From $512 per night (USD)VRBO
From $771 per night (USD)Expedia
307 65th Street managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
VRC 18-000047 Luxury Vacation Rental on Anna Maria Island – Steps from the Beach! Welcome to your dream getaway on Anna ...
From $771 per night (USD)Expedia
From $435 per night (USD)VRBO
Northshore Villa - 3 Bedroom, 2 Bathroom Vacation Rental Across from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come for the SUN, stay for the FUN!!! Find everything that makes a fun beach getaway on Anna Maria Island memorable whe ...
From $435 per night (USD)VRBO
From $621 per night (USD)Expedia
Large Single Level-1 Minute Walk To The Beach-5 minute walk to Restaurant/Shops
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Recently renovated with all new kitchens and more! Welcome to our Blue Grotto on the beautiful Anna Maria Island. We h ...
From $621 per night (USD)Expedia
From $432 per night (USD)VRBO
Private Pool - Summer Breeze by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3 ...
From $432 per night (USD)VRBO
From $209 per night (USD)VRBO
Enjoy the Island Life on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The location is very quiet and private. It's a short walk to Holmes Beach, Duffy s Tavern, Hurricane Hanks, The Feast, ...
From $209 per night (USD)VRBO