Holmes Beach Rentals
From $273 per night (USD)VRBO
Orchid Villa by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Orchid Villa at Island Garden Villas, where coastal elegance meets tropical serenity. *Features include* * ...
From $273 per night (USD)VRBO
From $321 per night (USD)Expedia
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Vrc16-000291 Distance to the ...
From $321 per night (USD)Expedia
From $337 per night (USD)VRBO
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Vrc19-000138 Community pool. ...
From $337 per night (USD)VRBO
From $526 per night (USD)Expedia
Mermaid's Crossing managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🌴 Mermaid's Crossing by Beach Retreats Vacation Rentals 📍 210 65th St, Holmes Beach, FL 34217 🪪 VRC17-000007 🏡 4 Bed ...
From $526 per night (USD)Expedia
From $277 per night (USD)VRBO
Seaside Beach House 203 · Top Floor · 14-Ft Balcony · Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
VRC20-000296 1BR · 1.5BA · Sleeps 3 · Top Floor · 14-Ft Private Balcony · 950+ Sq Ft · Dolphins from Balcony · No Eleva ...
From $277 per night (USD)VRBO
From $291 per night (USD)Expedia
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea La Vie by Anna Maria Life Vacation Rentals 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $291 per night (USD)Expedia
From $426 per night (USD)VRBO
Florida Breeze: Pool home in perfect central location!
- Bedrooms:
- 2
- 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 $426 per night (USD)VRBO
From $396 per night (USD)VRBO
Windshore A! - ~200 Steps to the Beach, Private Heated Pool, Beach Items, Wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully renovated in 2025, our Windshore A leaves no wishes open when it comes to your vacation on Anna Maria Island. Only ...
From $396 per night (USD)VRBO
From $318 per night (USD)VRBO
August Savings - Perfect Location - Pool + Sundeck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
August Deals! Special discounted rates are available this month. Don’t miss your chance to squeeze in one last summer ge ...
From $318 per night (USD)VRBO
From $246 per night (USD)Expedia
Blue Agave Villa by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Blue Agave Villa is a tr ...
From $246 per night (USD)Expedia
From $436 per night (USD)VRBO
Turtle Nest! Private Heated Pool and Access to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $436 per night (USD)VRBO
From $256 per night (USD)Expedia
Townhome with Private Outdoor Living Space, Community Pool - Sea La Vie
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea La Vie by AMI Locals VRC21-000203 Welcome to the relaxed coastal vibe of Sea La Vie, a modern three-bedroom, three ...
From $256 per night (USD)Expedia
From $209 per night (USD)VRBO
Anthony Beach Cottages - Italian Retreat - 2 bedroom home with pool - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Whether you are talking about the Florida Peninsula or the Sorrento Peninsula, everyone loves the beach! Two hurricanes ...
From $209 per night (USD)VRBO
From $556 per night (USD)Expedia
Seahorse Cottage! Walk to Beach & Shops!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seahorse Cottage by AMI Locals VRC16-000110 Welcome to Seahorse Cottage, a beautifully designed three-bedroom, three ...
From $556 per night (USD)Expedia
From $80 per night (USD)VRBO
Great Island Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2 BR/2 BA condo is all about charm and comfort. You will have no problem leaving your cares behind and en ...
From $80 per night (USD)VRBO
From $252 per night (USD)Expedia
The Island Easy - Walk to Beach - Pool View Balcony - Dog Friendly - King Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Island Easy, a dog-friendly, one-bedroom condo on Anna Maria Island just a short walk from the beach. Per ...
From $252 per night (USD)Expedia
From $359 per night (USD)VRBO
Island Time: Gulf front condo 20 ft to the beach with shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $359 per night (USD)VRBO
From $287 per night (USD)VRBO
Closer to the beach does not work: comfortable apartment at ground level on the beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ATTENTION: We rent with 1 week minimum: Saturday to Saturday Old Florida Feeling: bungalow right on the beach on level - ...
From $287 per night (USD)VRBO
From $348 per night (USD)VRBO
Cozy AMI Escape, Steps to Beach & Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Short walk to the beach • 2 Bedrooms | 2 Bathrooms | Sleeps 6 • King primary suite • Queen bed ...
From $348 per night (USD)VRBO
From $522 per night (USD)Expedia
⚓ Heated pool, Hot Tub, Games & More, 5 min> walk to beach!⚓🐕🏖🌅
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sweet Home Anna Maria! ⚓Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! ⚓Private ...
From $522 per night (USD)Expedia
From $296 per night (USD)VRBO
Egret at Blue Lagoon Unit 3 Anna Maria Island - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $296 per night (USD)VRBO
From $343 per night (USD)Expedia
Sea Glass on Anna Maria - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
When you arrive at “SeaGlass” you are greeted with pleasant landscaping, a gorgeous brick driveway, and an adorable home ...
From $343 per night (USD)Expedia
From $849 per night (USD)VRBO
TRUE BEACHFRONT HOME DIRECTLY ON SUGAR WHITE SANDS WITH HEATED POOL - IDYLLIC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
IN THE EVENT OF A MANDATORY EVACUATION DUE TO A STORM/HURRICANE ALL GUESTS WILL RECEIVE A FULL REFUND. Gaze Vacations ...
From $849 per night (USD)VRBO
From $390 per night (USD)VRBO
Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wi-Fi, Steps to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Dragonfly Breeze, a 3 bedroom and 2 bathroom elevated private pool home located in Holmes Beach, just a short ...
From $390 per night (USD)VRBO
From $447 per night (USD)VRBO
Summer Wind- An island getaway in the perfect location.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $447 per night (USD)VRBO
From $233 per night (USD)Expedia
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $233 per night (USD)Expedia
From $316 per night (USD)VRBO
Swizzle On The Sound · Saltwater Pool · 30-Night Minimum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VRC21-000048 3BR · 2BA · Sleeps 8 · 30-Night Minimum · Heated Saltwater Pool ($15/Day) · Six Outdoor Zones · Cedar Pavi ...
From $316 per night (USD)VRBO
From $222 per night (USD)Expedia
LOCATION!! Cabana just steps from the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to Anna Maria Island the # 1 spot for a perfect getaway. Bask in the tropical paradise of AMI with white sugar ...
From $222 per night (USD)Expedia
From $435 per night (USD)VRBO
Island Charm, Luxury Location & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Just steps from the beautiful Gulf beaches • Private heated pool • 2 King Bedrooms | 2.5 Bathro ...
From $435 per night (USD)VRBO
From $1573 per night (USD)Expedia
Family Tides, Great for groups, Ocean View, Pool/Waterfall, Spa, Golf Cart Incl.
- Bedrooms:
- 9
- Bathrooms:
- 10
- Sleeps:
- 24
Perfect for large families or groups, this property delivers a unique holiday experience bolstered by standout features ...
From $1573 per night (USD)Expedia
From $303 per night (USD)VRBO
Salty Harbor AMI pool retreat near the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 ...
From $303 per night (USD)VRBO
From $575 per night (USD)Expedia
AMI Oasis Heated Pool, Spa, Golf Cart, Putting Green, TikiBar, Sundeck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Immerse yourself in luxurious living in our updated property. Unwind by the calming heated pool, sip on a drink from the ...
From $575 per night (USD)Expedia
From $181 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 $181 per night (USD)VRBO
From $850 per night (USD)Expedia
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $850 per night (USD)Expedia
From $335 per night (USD)VRBO
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $335 per night (USD)VRBO
From $200 per night (USD)Expedia
Crow's Nest Spinnakers Cottages: 250 Steps to Beach! Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Crow's Nest Spinnakers Cottages by Anna Maria Life Vacation Rentals 202 56th St. #2, Holmes Beach, FL 34217 What You'll ...
From $200 per night (USD)Expedia
From $457 per night (USD)VRBO
Starfish Isle managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🌴 Starfish Isle by Beach Retreats Vacation Rentals 📍 5803 Holmes Blvd Holmes Beach, FL 34217 🪪 VRC 21-000046 🏡 4 Bed ...
From $457 per night (USD)VRBO
From $540 per night (USD)Expedia
Conch Out Beach House managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🐚 Conch-Out Beach House 📍 303 68th St, Holmes Beach, FL 34217 📌 VRC19-000273 🏡 4 Bedrooms | 3 Bathrooms | Sleeps 8 | ...
From $540 per night (USD)Expedia
From $362 per night (USD)VRBO
Starfish Cove managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Starfish Cove by Beach Retreats Vacation Rentals 📍 302 60th Street Holmes Beach, FL 34217 🪪 VRC19-000274 🏡 ...
From $362 per night (USD)VRBO
From $189 per night (USD)Expedia
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $189 per night (USD)Expedia
From $323 per night (USD)VRBO
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $323 per night (USD)VRBO
From $296 per night (USD)Expedia
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $296 per night (USD)Expedia
From $356 per night (USD)VRBO
Chic Pool Home Steps to Beach! Game Room and Paddleboards
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Pure Beach by AMI Locals VRC21-000101 Welcome to Pure Beach by AMI Locals, a luxurious three-bedroom, three-bath vaca ...
From $356 per night (USD)VRBO
From $688 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
Welcome to the Blue Grotto — Your 3,700 sq ft Island Playground! Recently renovated with all-new kitchens and more! Kic ...
From $688 per night (USD)Expedia
From $570 per night (USD)VRBO
Private Pool - Summer Breeze by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER 10/10/25 WITH A CHECK-IN DATE AFTER 1/17/26! All Drivers ...
From $570 per night (USD)VRBO
From $318 per night (USD)Expedia
One Bedroom Island Luxury Cottage located less than 2 blocks from the beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Flop Cottage located 1 block from the Gulf beaches of Anna Maria Island. Flop Cottage is a ground level half ...
From $318 per night (USD)Expedia
From $1244 per night (USD)VRBO
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is in the monthly rental ...
From $1244 per night (USD)VRBO
From $714 per night (USD)Expedia
Luxury Villa · Heated Saltwater Pool & Spa · Steps to Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Prime Location – Steps to the Beach! Luxurious ground-level villa at 124 50th Street, Holmes Beach, in the heart of Anna ...
From $714 per night (USD)Expedia
From $158 per night (USD)VRBO
Cabin 2 Spinnakers Cottages: Dog Friendly - 250 Steps to Beach Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cabin 2 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #2, Holmes Beach, FL 34217 What You'll Lov ...
From $158 per night (USD)VRBO
From $965 per night (USD)Expedia
BUENA VISTA 4 - LUXURY BEACHFRONT - Anna Maria Island - By Island Real Estate Va
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Top 10 Gulfview on Anna Maria Island!!! You can see for miles in both direction down the beach. Luxury condominium “Buen ...
From $965 per night (USD)Expedia
From $1251 per night (USD)VRBO
Buena Vista 3 - DIRECT BEACHFRONT Luxury Condo - Anna Maria Island- By Island Re
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DIRECT BEACH FRONT - Luxury 4BR Condo - Buena Vista #3 - 101 67th Street - 4 Bedrooms and 3 and a 1/2 Baths - Bed/s: 3 ...
From $1251 per night (USD)VRBO
From $941 per night (USD)Expedia
Anna Maria Island Waterfront house with private pool, spa, elevator and dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaway ...
From $941 per night (USD)Expedia
From $409 per night (USD)VRBO
Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spend your Anna Maria Island vacation in five star luxury when you visit “Aquarius”. This fully renovated Holmes Beach v ...
From $409 per night (USD)VRBO
From $291 per night (USD)Expedia
Breezy Harbor AMI pool retreat near the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for ...
From $291 per night (USD)Expedia
From $1131 per night (USD)VRBO
Buena Vista #2: Luxury Beach Front Condo, Amazing Views, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Buena Vista #2 by Anna Maria Life Vacation Rentals 101 67th St #2, Holmes Beach, FL 34217 What You'll Love About This H ...
From $1131 per night (USD)VRBO
From $202 per night (USD)Expedia
Modern Beach House, 1 Block from beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Anna Maria Island Vacation Home is located just a few houses from the white sand beaches! Holmes Beach is ...
From $202 per night (USD)Expedia
From $944 per night (USD)VRBO
GLORIOUS DAZE Beach House POOL! SPA! GOLFCART! ELEVATOR! PUTTING GREEN!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Glorious Daze! Our four bedroom/four bath private home is located along the sugary white sands of beautiful H ...
From $944 per night (USD)VRBO
From $370 per night (USD)Expedia
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 🏝 Caribbean Surf by Beach Retreats Vacation Rentals 📍 Hol ...
From $370 per night (USD)Expedia
From $676 per night (USD)VRBO
307 65th Street managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
🏖 Island Escape by Beach Retreats Vacation Rentals 📍 307 65th St, Holmes Beach, FL 34217 🏡 VRC18-000047 Your dream ge ...
From $676 per night (USD)VRBO
From $489 per night (USD)Expedia
Ground Floor Luxury 4BR Home · Heated Saltwater Pool & Spa · Very Close to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to AMI Beach Home in Holmes Beach on beautiful Anna Maria Island. This custom-built ground-floor vacation home ...
From $489 per night (USD)Expedia
From $309 per night (USD)VRBO
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Getaway by Anna Maria Life Vacation Rentals 205 56th St., Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $309 per night (USD)VRBO
From $386 per night (USD)Expedia
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Gumbo Cottage located just 7 houses from the Gulf beaches of Anna Maria Island and a street away from downtow ...
From $386 per night (USD)Expedia
From $320 per night (USD)VRBO
Old Florida Beach Escape – Steps to the Gulf 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 $320 per night (USD)VRBO
From $448 per night (USD)Expedia
Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Minnie Cottage 125 47th Street, Holmes Beach, FL 34217 VRC20-000146 What you will love about this property: • Short stro ...
From $448 per night (USD)Expedia
From $276 per night (USD)VRBO
EXCELLENT LOCATION IN THE HEART OF HOLMES BEACH ON ANNA MARIA ISLAND!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated in 2025, bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minu ...
From $276 per night (USD)VRBO
From $220 per night (USD)Expedia
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 $220 per night (USD)Expedia
From $323 per night (USD)VRBO
Sandy Cheeks & Barefeet, Gorgeous interior Gulf beach Place, pool, on beach side
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ST Lic CND5101424 City licVRC23-000018 Gulf views from several rooms and lanai! Quick access (only 1 small house betw ...
From $323 per night (USD)VRBO
From $484 per night (USD)Expedia
Sunkissed by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunkissed is a beautiful elevated townhome that is located in Holmes Beach-just a short stroll to the gorgeous white san ...
From $484 per night (USD)Expedia
From $213 per night (USD)VRBO
Sea Pirate 7 · Renovated 2026 · Pool · Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000815 2BR · 1BA · Sleeps 4 · 2026 Complete Renovation · Across from Gulf · Heated Pool · Private Fenced Patio · ...
From $213 per night (USD)VRBO
From $426 per night (USD)Expedia
Kickback Cabana managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌊 Kickback Cabana 📍411 79th Street Holmes Beach FL 34217 🪪 VRC19-000189 🏡 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Heat ...
From $426 per night (USD)Expedia
From $173 per night (USD)VRBO
Island Retreat by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds an ...
From $173 per night (USD)VRBO
From $385 per night (USD)Expedia
Enjoy the Gulf’s turquoise waters at Bryant’s Beach Bungalow!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You want this- 400 steps to the most amazing beach you’ll find yourself dreaming about every time you plan a vacation! T ...
From $385 per night (USD)Expedia
From $289 per night (USD)VRBO
Beach Days & Dog-Friendly AM Island Adventures
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Short walk to the Gulf beaches via North Beach Village • Quiet residential location • 2 Bedroom ...
From $289 per night (USD)VRBO
From $235 per night (USD)Expedia
Beach Potato: Gulf View Condo, Pool, Steps to the beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beach Potato by Anna Maria Life Vacation Rentals 3404 Gulf Drive, #5, Holmes Beach, FL 34217 What You'll Love Ab ...
From $235 per night (USD)Expedia
From $242 per night (USD)VRBO
Barefoot Dreams: Dog Friendly, Private Pool,1 Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Barefoot Dreams by Anna Maria Life Vacation Rentals 201 76th St. East Unit B, Holmes Beach, FL 34217 What You'll Love A ...
From $242 per night (USD)VRBO
From $670 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 $670 per night (USD)VRBO
From $316 per night (USD)VRBO
BeachView Condo #8 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 6 people. 5 min. walk to the beach. Community pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach View Condominum, #8 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 6 people. Vrc22-000101 Communi ...
From $316 per night (USD)VRBO
From $322 per night (USD)Expedia
2-Min Walk to Holmes Beach - Walk to Shops & Dining - Quiet Tropical Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet, tropical townhouse is just a 2-min walk to Holmes Beach, tucked away from the crowds in a private Cul de Sac, yet ...
From $322 per night (USD)Expedia
From $429 per night (USD)VRBO
10/10 Rating - A Pearl of a Beach Home- private pool & spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical rear yard with private luxury heated pool and integrated hot tub/spa and spacious paved area plus large ground ...
From $429 per night (USD)VRBO
From $222 per night (USD)Expedia
Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
VRC16-000018 Cottage By the Sea is a (no smoking) Unit within the charming Sea Pirate condo complex located on a tra ...
From $222 per night (USD)Expedia
From $305 per night (USD)VRBO
SS Salamander North · Pool & Fire Pit · Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
VRC16-000499 2BR · 1.5BA · Sleeps 5 · Very Short Walk to Gulf · Heated Pool · Fire Pit Table · Gas Grill · Outdoor Show ...
From $305 per night (USD)VRBO
From $321 per night (USD)Expedia
Horizonwest #112 -Steps to Beach -2BD-Sunset Balcony’s
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Holmes Beach Favorite! Spacious 2 bedroom 2 full bath condo is just steps to the beach. Updated kitchen and ne ...
From $321 per night (USD)Expedia
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An Island Retreat with Lagoon Style Pool, close to Bay and Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This inviting home offers the perfect blend of relaxation and convenience, featuring a lagoon-style pool that creates a ...
Click For PricingVRBO
From $685 per night (USD)Expedia
She's Always Right - Pet Home w/ Pool, Spa, Steps to Beach & Prime AMI Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to She's Always Right! On Anna Maria Island (Holmes Beach, FL) The Space Where thoughtful design meets island e ...
From $685 per night (USD)Expedia
From $794 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 $794 per night (USD)VRBO
From $401 per night (USD)Expedia
2 Bedroom / 2 Bath Ground Level With a Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for a Weekly rental located in the heart of Anna Maria Island at 305 61st St, Unit A, Holmes Beach, FL, ...
From $401 per night (USD)Expedia
From $260 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 $260 per night (USD)VRBO
From $513 per night (USD)Expedia
Beautiful home with fenced yard, heated pool, hot tub, and elevator!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Sand Castle by Anna Maria Island Accommodations VRC19-000022 Welcome to Sand Castle by Anna Maria Island Accommodatio ...
From $513 per night (USD)Expedia
From $284 per night (USD)VRBO
Bamboo Breeze! Cozy Pool Retreat Near Shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bamboo Breeze by Anna Maria Island Accommodations VRC16-000181 Welcome to Bamboo Breeze, a charming two-bedroom, two- ...
From $284 per night (USD)VRBO
From $186 per night (USD)Expedia
Holmes Beach Condo with Pool and Balcony! 3 Minutes to Beach - Seabreeze D
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seabreeze D by Anna Maria Island Accommodations VRC16-000111 Welcome to Seabreeze D, a charming two-bedroom, two-bath ...
From $186 per night (USD)Expedia
From $518 per night (USD)VRBO
Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Simply Chic by Anna Maria Island Accommodations VRC16-000105 Discover Simply Chic, a stylish four-bedroom, three-bath ...
From $518 per night (USD)VRBO
From $335 per night (USD)Expedia
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Breeze Villa B by Anna Maria Island Accommodations VRC16-000146 Escape to Gulf Breeze Villa B, a cozy one-bedroo ...
From $335 per night (USD)Expedia
From $815 per night (USD)VRBO
It's a Jungle Out There - Tropical Pool, Sunset Views, Game Room!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
It’s a Jungle Out There by Anna Maria Island Accommodations VRC19-000173 Welcome to It’s a Jungle Out There by Anna M ...
From $815 per night (USD)VRBO
From $220 per night (USD)Expedia
Ground-level AMI Condo Near the Beach! Large heated pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Palm Cay 6 by Anna Maria Island Accommodations VRC16-000127 Welcome to Palm Cay 6, a charming ground-level corner c ...
From $220 per night (USD)Expedia
From $479 per night (USD)VRBO
Luxury home with Pool, Spa, and Dock -Bayshores
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayshores by Anna Maria Island Accommodations VRC18-000040 Welcome to Bayshores by Anna Maria Island Accommodations, ...
From $479 per night (USD)VRBO
From $190 per night (USD)Expedia
Condo with Pool! Near the Beach, Shops, and Dining! - Seabreeze A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seabreeze A by Anna Maria Island Accommodations VRC16-000112 Welcome to Seabreeze A, the perfect family-friendly co ...
From $190 per night (USD)Expedia
From $388 per night (USD)VRBO
Beach Cottage! Walk to Dining, Shops and Island Trolley Stop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beach Cottage by Anna Maria Island Accommodations VRC16-000178 Welcome to Beach Cottage, a charming ground-level vaca ...
From $388 per night (USD)VRBO
From $424 per night (USD)Expedia
Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun Daze by Anna Maria Island Accommodations VRC16-000103 Welcome to Sun Daze by Anna Maria Island Accommodations, a ...
From $424 per night (USD)Expedia
From $397 per night (USD)VRBO
Beautifully outfitted home with a heated pool and tropical backyard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seahorse Paradise by Anna Maria Island Accommodations VRC16-000108 Welcome to Seahorse Paradise by Anna Maria Island ...
From $397 per night (USD)VRBO
From $369 per night (USD)Expedia
Enjoy Endless Fun with a Private Heated Pool at Key Largo Cottage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Key Largo Cottage by Anna Maria Island Accommodations VRC18-000120 Discover the ultimate family getaway at Key Largo ...
From $369 per night (USD)Expedia