Holmes Beach Rentals
From $507 per night (USD)VRBO
Our Blue Heaven boasts one of the LARGEST PRIVATE POOLS on AMI!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our Blue Heaven (OBH) is located on a corner lot in a quiet, residential neighborhood a short, straight block's walk to ...
From $507 per night (USD)VRBO
From $260 per night (USD)Expedia
Sandpiper at Blue Lagoon Unit 5 - by Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will fall in love! Beautiful two bedroom, two bath villa in one of Anna Maria Islands premier vacation communities c ...
From $260 per night (USD)Expedia
From $250 per night (USD)VRBO
Palm Isle Village 3215 - Anna Maria Condo with Pool - By Island Real Estate Vaca
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Disclaimer: Discoloration in the pool is from staining, not dirt or debris in the pool, and the pool is safe and clean f ...
From $250 per night (USD)VRBO
From $356 per night (USD)Expedia
Bikinis and Board Shorts A: Private pool, 2-mins to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bring your bikinis and board shorts to this lovely 2 bedroom, 1 bath villa a short block to the gorgeous white sand beac ...
From $356 per night (USD)Expedia
From $355 per night (USD)VRBO
Bikinis and Board Shorts B: Private pool, 2-mins to beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bring your bikinis and board shorts to this lovely 2 bedroom, 2 bath villa a short block to the gorgeous white sand beac ...
From $355 per night (USD)VRBO
From $533 per night (USD)Expedia
Steps from AMI Sands, Private Pool & Pets Welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Easy beach access with no streets to cross • 3 Bedrooms | 2.5 Bathrooms | Sleeps 6 • King prima ...
From $533 per night (USD)Expedia
From $638 per night (USD)VRBO
Coral Escape: 6-Bedroom Anna Maria Island Home with Pool and Spa! 1 Block to Bea
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Coral Escape by AMI Locals VRC18-000089 Welcome to Coral Escape by AMI Locals, a stunning 6-bedroom, 4-bathroom coast ...
From $638 per night (USD)VRBO
From $950 per night (USD)Expedia
Beautiful luxury home! Pool, rooftop deck and steps from the beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Avalon by AMI Locals VRC18-000082 Welcome to Avalon by AMI Locals, a luxury 4-bedroom, 3.5-bathroom coastal home just ...
From $950 per night (USD)Expedia
From $268 per night (USD)VRBO
Caribbean Reef! Cozy Pool Home Near Gulf!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Caribbean Reef by AMI Locals VRC18-000084 Welcome to Caribbean Reef, an inviting three-bedroom, two-bathroom Holmes B ...
From $268 per night (USD)VRBO
From $492 per night (USD)Expedia
Luxury Home with Private Pool and Spa! Short Walk to Beach! - Mojito Splash
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Mojito Splash by AMI Locals VRC18-000068 Welcome to Mojito Splash, a stunning five-bedroom, three and a half bath w ...
From $492 per night (USD)Expedia
From $331 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 $331 per night (USD)VRBO
From $359 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 $359 per night (USD)Expedia
From $359 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 $359 per night (USD)VRBO
From $287 per night (USD)Expedia
Pool Party South · 3BR · Pool & Spa · Updated Jan 2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000497 3BR · 2BA · Sleeps 6 · Jan 2025 Remodel · Shared Heated Pool & Spa · Outdoor Bar · Gas Grill · Pet-Friendl ...
From $287 per night (USD)Expedia
From $357 per night (USD)VRBO
2 Min Walk to Gulf Beaches, Heated Pool, XL Lanai, Gas Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whispering Palms Villa at North Beach Village is a bright, sunny, and beautifully decorated coastal-style townhouse tuck ...
From $357 per night (USD)VRBO
From $428 per night (USD)Expedia
Beautiful Bungalow with Private Pool! Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Day Break Bungalow by AMI Locals VRC19-000140 Experience the ultimate beachside escape at Day Break Bungalow, a beaut ...
From $428 per night (USD)Expedia
From $263 per night (USD)VRBO
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 $263 per night (USD)VRBO
From $610 per night (USD)Expedia
The Tiki Treehouse: Luxury Beach Retreat at Grassy Point Nature Preserve
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Seven beds nestled among manicured palm trees and mangroves, two minutes' walk to America's best beach. Bonus lounge en ...
From $610 per night (USD)Expedia
From $661 per night (USD)VRBO
Gone Coastal Duplex by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the ultimate family vacation getaway. This amazing house is a full duplex rental with a total of 4 bedrooms a ...
From $661 per night (USD)VRBO
From $351 per night (USD)Expedia
Gone Coastal Too by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Gone Coastal, Too! This sister property to Gone Coastal has all the comforts of home. *Features include* * ...
From $351 per night (USD)Expedia
From $577 per night (USD)VRBO
On the Beach: Breathtaking 180 degree views of Gulf of Mexico
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful 5-bedroom, 4-bathroom vacation home in Holmes Beach is just steps from the beach with fantastic Gulf view ...
From $577 per night (USD)VRBO
From $228 per night (USD)VRBO
Terrific 2-bedroom apartment in Holmes Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Anna Maria Island is a stunning destination in Florida, known for its serene atmosphere and easy accessibility. The isla ...
From $228 per night (USD)VRBO
From $503 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 $503 per night (USD)VRBO
From $133 per night (USD)Expedia
SUPER CLEAN @ Sunbow Bay. Sleeps 6, easy walk to gulf/groceries, nice amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CLEAN, CLEAN, CLEAN!! This beautiful, clean and conveniently located Holmes Beach condo has fresh furnishings and nice, ...
From $133 per night (USD)Expedia
From $366 per night (USD)VRBO
Perfect Family Vacation Home with Private Pool and Tropical Landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Bella by AMI Locals VRC22-000114 Experience the ultimate island retreat at Casa Bella, a luxurious corner lot v ...
From $366 per night (USD)VRBO
From $346 per night (USD)Expedia
Private pool and close to beach! Near shopping and dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Blissful Bungalow by AMI Locals VRC21-000131 Welcome to Blissful Bungalow by AMI Locals, a stylish three bedroom, two ...
From $346 per night (USD)Expedia
From $224 per night (USD)VRBO
Steps to Beach - Sea Pirate Unit 6 by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will ma ...
From $224 per night (USD)VRBO
From $500 per night (USD)Expedia
Luxury Poolside Living, AMI Beach & Pets Welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Just a 2-minute walk to the beautiful Gulf beaches • Private heated pool and spa with spacious s ...
From $500 per night (USD)Expedia
From $419 per night (USD)VRBO
Beach Days, Poolside Nights & Island Memories
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Short walk to Anna Maria Island's beautiful beaches • Private heated pool • 3 Bedrooms + Bonus ...
From $419 per night (USD)VRBO
From $481 per night (USD)Expedia
Steps to the beach! PRIVATE HEATED POOL w covered lanai. Central location.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two minute walk to beach access at the end of our street! PRIVATE heated pool. Air conditioned 2 bedroom 2 bath home. P ...
From $481 per night (USD)Expedia
From $466 per night (USD)VRBO
Two minute walk to beach! PRIVATE HEATED POOL w covered lanai. Great location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two minute walk to beach access at the end of our street! PRIVATE heated pool. Air conditioned 2 bedroom 2 bath home. P ...
From $466 per night (USD)VRBO
From $383 per night (USD)Expedia
GREAT COTTAGE w/Heated Pool, Dog- See Note - Allowed | Prime Beach Location | Dog-Friendly | Sleeps 6 | Steps to Beach, Dining...
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST-MINUTE DEALS! Welcome to “The Sandbox”, a charming 2-bedroom, 1.5-bath coastal cottage just one house ...
From $383 per night (USD)Expedia
From $369 per night (USD)VRBO
Promise Kept - Holmes Beach Pool Home Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the perfect island getaway? Look no further than Promise Kept! This home is centrally located on Anna Maria ...
From $369 per night (USD)VRBO
From $881 per night (USD)Expedia
Just Beachy managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
🌊 Just Beachy – Your Luxury Island Retreat on Anna Maria Island 📍128 49th Street Holmes Beach FL 34217 🪪 VRC21-000019 ...
From $881 per night (USD)Expedia
From $249 per night (USD)VRBO
Sea Pirate 2- Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
"Sea Pirate 2" is a bright and sunny, ground-floor vacation rental condo that features beach decor, has an oversized hea ...
From $249 per night (USD)VRBO
From $208 per night (USD)Expedia
Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy quiet sunsets from your private screened balcony at this two bedroom two bathroom third floor condo with preserve ...
From $208 per night (USD)Expedia
From $987 per night (USD)VRBO
Lux Ocean View 4x4 for the Holidays!
- 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 $987 per night (USD)VRBO
From $410 per night (USD)Expedia
Beachfront - Sun Plaza West 214 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sun Plaza West is a beautiful beachfront property offering all of the conveniences you would want in an island stay. Thi ...
From $410 per night (USD)Expedia
From $282 per night (USD)VRBO
Beach House Anna Maria Island, FL - 1 block to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this beautiful home in North Beach Village on Anna Maria Island, where coastal charm and exceptional privacy ...
From $282 per night (USD)VRBO
From $183 per night (USD)Expedia
West Bay Cove 216 · Pool Views · 30-Night Min · Renovated 2026
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC20-000192 2BR · 2BA · Sleeps 4 · 30-Night Minimum · Two Heated Pools · Tennis Court · 5-Min Walk to Manatee Beach · ...
From $183 per night (USD)Expedia
From $234 per night (USD)VRBO
⚓5400 Gulf Dr! 55+ condo with amazing pool just steps away from the beach!⚓🏖
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Gulf Drive 5400! ⚓55+ Community, Heated Pools ⚓Short walk to the World Class Beaches of Anna Maria Island ⚓Fu ...
From $234 per night (USD)VRBO
From $167 per night (USD)Expedia
West Bay Cove 226 · Kayak Launch · For Sale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
VRC20-000180 1BR · 1BA · Sleeps 6 · 30-Night Minimum · Kayak & Paddleboard Launch · Two Heated Pools · Tennis Court · 5 ...
From $167 per night (USD)Expedia
From $314 per night (USD)VRBO
Modern Coastal Home, Private Pool, Close to the beach with beach gear and grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into the tranquil elegance of Hal's Haven, a delightful two-bedroom, two-bathroom retreat nestled in the heart of H ...
From $314 per night (USD)VRBO
From $248 per night (USD)Expedia
The Palms 4 · Veteran Discount · Bikes & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000097 2BR · 2BA · Sleeps 6 · Pet-Friendly · 1 Block to Gulf · Heated Pool (4 Units) · King Bed · 2 Bikes & Wagon ...
From $248 per night (USD)Expedia
From $871 per night (USD)VRBO
AMI Retreat! Pool, Spa, Ping Pong and Walk to Holmes Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Seas the Day by AMI Locals VRC22-000025 Welcome to Seas the Day by AMI Locals, an extraordinary six-bedroom, five-bat ...
From $871 per night (USD)VRBO
From $253 per night (USD)Expedia
Liddie's Place: Gulf Front Sun Plaza West Condo, Pool, Tennis by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Liddie's Place by Anna Maria Life Vacation Rentals 5608 Gulf Drive, #209, Holmes Beach, FL 34217 What You'll Love ...
From $253 per night (USD)Expedia
From $511 per night (USD)VRBO
Updated Home with Outdoor Dining and heated Pool! 2 Minutes to Beach! - Native S
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Native Sun by AMI Locals VR22-000055 Welcome to Native Sun, a beautifully updated coastal home featuring four bedro ...
From $511 per night (USD)VRBO
From $1316 per night (USD)Expedia
PERFECT 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 $1316 per night (USD)Expedia
From $315 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 $315 per night (USD)VRBO
From $442 per night (USD)Expedia
Our Waterfront Home Is All Ready Just For You! VRC16-000016
- 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 $442 per night (USD)Expedia
From $267 per night (USD)VRBO
La Playita 7 · Two Kings · Rec Room · Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC21-000073 2BR · 2BA · Sleeps 6 · Townhome · Two King Beds · Private Rec Room · Heated Pool · 2 Blocks to Gulf · Walk ...
From $267 per night (USD)VRBO
From $254 per night (USD)Expedia
Beach n It: Dog Friendly, Pool, Convenient to all of AMI by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach n It by Anna Maria Life Vacation Rentals 410 Bay Palms Dr., Holmes Beach, FL 34217 What you'll love about this ho ...
From $254 per night (USD)Expedia
From $296 per night (USD)VRBO
Steps to Beach - Tropical Sunset 2 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located right across the street from the world-famous Anna Maria Island beaches, this two-bedroom condo is newly remodel ...
From $296 per night (USD)VRBO
From $417 per night (USD)Expedia
Mello on the Beach - Fanta Sea
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $417 per night (USD)Expedia
From $824 per night (USD)VRBO
Mello on the Beach - High Tide
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $824 per night (USD)VRBO
From $592 per night (USD)Expedia
Mello on the Beach - Vitamin Sea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $592 per night (USD)Expedia
From $417 per night (USD)VRBO
Mello on the Beach - Shore Enuff
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $417 per night (USD)VRBO
From $461 per night (USD)Expedia
Mello on the Beach - Looney Dunes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $461 per night (USD)Expedia
From $417 per night (USD)VRBO
Mello on the Beach - Hip Nautic
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $417 per night (USD)VRBO
From $475 per night (USD)Expedia
Mello on the Beach - Slow M'Ocean
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The best view in the house awaits at Slow M'Ocean. Beaming with natural light from oversized windows, you’ll discover pi ...
From $475 per night (USD)Expedia
From $417 per night (USD)VRBO
Mello on the Beach - Sea Duced
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $417 per night (USD)VRBO
From $461 per night (USD)Expedia
Mello on the Beach - Sol Mate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for post-beach lunch or a meal back at basecamp, our colorful kitchenettes feature refrigerator, dishwasher, sto ...
From $461 per night (USD)Expedia
From $281 per night (USD)VRBO
Charming Ground Level Resort Style 3 unit Condo - unit C
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your Perfect Beach Getaway! Escape to our beautifully updated ground-level unit C of a charming triplex, nes ...
From $281 per night (USD)VRBO
From $249 per night (USD)Expedia
Island Escape with Pool and Balcony! Near the Beach and Dining - Two Sisters
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two Sisters by Anna Maria Island Accommodations Escape to Two Sisters, an adorable three-bedroom, two-bath townhome ...
From $249 per night (USD)Expedia
From $543 per night (USD)VRBO
Resting Beach Place managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
🌴 Resting Beach Place 📍 5608 Gulf Dr, unit 111, Holmes Beach, FL 34217 🪪 VRC21-000018 🏡 2 Bedrooms | 2 Bathrooms | S ...
From $543 per night (USD)VRBO
From $434 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 $434 per night (USD)VRBO
From $399 per night (USD)VRBO
Close to beach, private heated pool, bikes, beach chairs & more!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
FULLY RENOVATED in November 2024! Salty Daze is a ground-level private accommodation nestled in the heart of Holmes Beac ...
From $399 per night (USD)VRBO
From $213 per night (USD)Expedia
Pool Access, Walk to Manatee Beach: Coastal Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3rd-Floor Unit | Central A/C | Screened-In Porch w/ Bay View Leave your worries behind and bring your flip flops and sw ...
From $213 per night (USD)Expedia
From $376 per night (USD)VRBO
Salt Shack - Ground Level Private Pool Villa - by Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The newly listed Salt Shack is an adorable 3 bedroom 2 bathroom beach escape on Anna Maria Island. This vacation rental ...
From $376 per night (USD)VRBO
From $210 per night (USD)Expedia
Palm Isle Village 3210- 1BR Condo with Pool - Anna Maria Island - By Island Real
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
*Disclaimer: Discoloration in the pool is from staining, not dirt or debris. The pool is safe and clean for swimming. Ac ...
From $210 per night (USD)Expedia
From $351 per night (USD)VRBO
Sea for Two: Gulf Front & On the Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
101 73rd St #4, Holmes Beach, FL 34217 What You'll Love About This Home: Location! On the Beach! 1 Bedroom / 1 Bathroo ...
From $351 per night (USD)VRBO
From $207 per night (USD)Expedia
Island Walk 207 · Bunk Beds · Mangrove Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC22-000237 2BR · 2BA · Sleeps 6 · Bunk Beds (Full over 2 Twins) · Rollaway & Crib Available · Mangrove View Lanai · H ...
From $207 per night (USD)Expedia
From $221 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 $221 per night (USD)VRBO
From $311 per night (USD)Expedia
August Deals Are Here! Pool • Private Sundeck • Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
August Deals Are Here! Enjoy special discounted rates throughout August and make the most of your final summer getaway. ...
From $311 per night (USD)Expedia
From $326 per night (USD)VRBO
Turtle Tyme: Dog Friendly, Pool, Putting Green, 2 Blocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Turtle Tyme by Anna Maria Life Vacation Rentals 4601 Gulf, Holmes Beach, FL 34217 What You'll Love About This Home: Loc ...
From $326 per night (USD)VRBO
From $737 per night (USD)Expedia
Getaway Retreat A+B · 4BR · Firepit · Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
4BR · 4BA · Sleeps 12 · Both Units · Pet-Friendly ($150/Pet) · 1 Block to Bay · Kayak Launch · Two Firepits & Gas Grills ...
From $737 per night (USD)Expedia
From $270 per night (USD)VRBO
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 $270 per night (USD)VRBO
From $731 per night (USD)Expedia
Luxury House with Temperature-controlled Pool in Private Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coconut Ranch - You will walk into an island lovers paradise when you walk into this Stunning Home. Even the ...
From $731 per night (USD)Expedia
From $564 per night (USD)VRBO
Pristine Anna Maria Island Beachfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking to experience Old World Florida charm with a modern twist, "The Sandy Turtle" - Gulf Place Condominium #D15 on A ...
From $564 per night (USD)VRBO
From $350 per night (USD)Expedia
Blue Egret: Pool, Enclosed Lanai, Close to the Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Egret by Anna Maria Life Vacation Rentals 306 61st St, Unit A (East Unit), Holmes Beach, FL 34217 What You'll Love ...
From $350 per night (USD)Expedia
From $192 per night (USD)VRBO
Blue Pelican: Sparkling Pool, Patio Dining, Close to the Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Pelican by Anna Maria Life Vacation Rentals 306 61st St, Unit B (West Unit), Holmes Beach, FL 34217 What You'll Lo ...
From $192 per night (USD)VRBO
From $324 per night (USD)Expedia
Single Level Home- 1 Minute Walk to the Beach- 5 minute walk to Restaurant/Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Blue Grotto — Your 1,850 sq ft Island Playground! Recently renovated with all-new kitchens and more! Kic ...
From $324 per night (USD)Expedia
From $203 per night (USD)VRBO
West Bay Cove 231 · Skyway Views · Sun Room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC20-000177 2BR · 2BA · Sleeps 4 · 1,275 Sq Ft · 30-Night Minimum · 19x10 Bay-Window Sun Room · Sunshine Skyway Bridge ...
From $203 per night (USD)VRBO
From $240 per night (USD)Expedia
West Bay Cove 238 · Skyway Views · 30-Night
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC20-000176 2BR · 2BA · Sleeps 4 · 30-Night Minimum · Bay Front · Sunshine Skyway Bridge Views · Floor-to-Ceiling Slid ...
From $240 per night (USD)Expedia
From $197 per night (USD)VRBO
Blue Bayou: Dog Friendly Home - 5 Houses to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Bayou by Anna Maria Life Vacation Rentals 201 76th St. West Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $197 per night (USD)VRBO
From $231 per night (USD)Expedia
Beautiful Condo with Beach views! Rest and Relaxation await!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Water’s Edge 205 by AMI Locals VRC21-000026 Experience the ultimate beachfront escape at Water’s Edge 205, a beauti ...
From $231 per night (USD)Expedia
From $240 per night (USD)VRBO
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $240 per night (USD)VRBO
From $486 per night (USD)VRBO
Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC# 19-000218 Cozy 'Day' Side Cottage is located in Holmes Beach on Anna Maria Island. It offers 2 bedrooms and 1 1/ ...
From $486 per night (USD)VRBO
From $293 per night (USD)VRBO
Groovy Guava by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Whether you're here for long beach days, sunset strolls, or cruising the island, Groovy Guava makes island life feel eff ...
From $293 per night (USD)VRBO
From $293 per night (USD)Expedia
Beach Daze by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you're spending your days at the beach or relaxing poolside in your private backyard oasis, Beach Daze makes it ...
From $293 per night (USD)Expedia
From $425 per night (USD)VRBO
Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Pineapple by Anna Maria Life Vacation Rentals 404 80th Street, Holmes Beach, FL 34217 What You'll Love About Th ...
From $425 per night (USD)VRBO
From $235 per night (USD)Expedia
Enjoy AMI sunsets | Chic home w/ Saltwater pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**** THIS IS UNIT 401 WHICH IS PART OF A DUPLEX- IF YOU LIKE TO RENT THE WHOLE DUPLEX INSTEAD PLEASE SEE OUR OTHER LISTI ...
From $235 per night (USD)Expedia
From $236 per night (USD)VRBO
Walk to beach | Anna Maria home w/ pool | Pets ok!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**** THIS IS UNIT 403 WHICH IS PART OF A DUPLEX- IF YOU LIKE TO RENT THE WHOLE DUPLEX INSTEAD PLEASE SEE OUR OTHER LISTI ...
From $236 per night (USD)VRBO
From $281 per night (USD)Expedia
Chasing Waves managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
🌴 Chasing Waves by Beach Retreats Vacation Rentals 📍 107 78th St, Holmes Beach, FL 34217 🪪 VRC21-000089 🏡 2 Bedrooms ...
From $281 per night (USD)Expedia
From $1254 per night (USD)VRBO
1 Block to Beach - LARGE Private Pool, 6 BDRM, Ranked Top 10% of Rentals on AMI
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Holmes Beach House For Rent - Luxury Vacation Rental on Anna Maria Island, Florida - Ranked in Top 10% of Rentals on AMI ...
From $1254 per night (USD)VRBO
From $417 per night (USD)Expedia
Beach Time AMI! Pet Friendly Home with Pool, Hot Tub and Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beach Time AMI by AMI Locals VRC19-000030 Welcome to Beach Time AMI, a five bedroom, three bath vacation home in Holm ...
From $417 per night (USD)Expedia
From $181 per night (USD)VRBO
West Bay Cove 142 · Pool Views · 30-Night Min
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
VRC20-000142 2BR · 2BA · Sleeps 5 · 30-Night Minimum · Pool & Courtyard Views · Two Heated Pools · Tennis Court · 5-Min ...
From $181 per night (USD)VRBO
From $243 per night (USD)Expedia
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa East is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $243 per night (USD)Expedia
From $851 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 condominium complex, 1 week minimum reservation req ...
From $851 per night (USD)VRBO
From $256 per night (USD)Expedia
West Bay Cove 131 · Skyway Views · 30-Night Min
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC20-000136 2BR · 2BA · Sleeps 4 · 30-Night Minimum · Bay Front · Sunshine Skyway Bridge Views · Kayak & Fish from Bac ...
From $256 per night (USD)Expedia