Holmes Beach Rentals
From $239 per night (USD)VRBO
Island Vibe 6: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Vibe 6, a newly renovated 2-bedroom, 2-bathroom pool home. This beautiful property will sleep 6 peop ...
From $239 per night (USD)VRBO
From $327 per night (USD)Expedia
Villa Sand Dollar by Anna Maria Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Villa Sand Dollar, a charming three-bedroom, two and a half bath Holmes Beach vacation rental just a 2-minute ...
From $327 per night (USD)Expedia
From $412 per night (USD)VRBO
Queen Palm: 2BR Duplex with Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Queen Palm, your charming island escape nestled in the heart of Anna Maria Island. This beautifully updated 2 ...
From $412 per night (USD)VRBO
From $467 per night (USD)Expedia
Coastal Vibes: Pool homes steps to the white sand beaches on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the best of beachside living in this beautifully reimagined ground-level 4-bedroom home, just one block from ...
From $467 per night (USD)Expedia
From $254 per night (USD)VRBO
Nautilus 118 by Nautilus Vacations-Beachfront Condo, Pool, Recreation Court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Nautilus! We are 34 individually owned and uniquely decorated condominiums available for vacation rentals ...
From $254 per night (USD)VRBO
From $292 per night (USD)Expedia
Anna Maria Island coastal chic 2 bed 2 bath beach condo with lots of amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
<p>Located in Holmes Beach, this welcoming condo lets you experience it all. Anna Maria Sound is just steps away and Bra ...
From $292 per night (USD)Expedia
From $253 per night (USD)VRBO
Sand Dollar- Perfect Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sand Dollar, a stunning vacation home featuring a sparkling pool and hot tub, just a short walk from Holmes B ...
From $253 per night (USD)VRBO
From $443 per night (USD)Expedia
7 minute walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and unwind at Banana Cabana, a charming three-bedroom, two-bath vacation home just minutes from Holmes Beach’s pow ...
From $443 per night (USD)Expedia
From $749 per night (USD)VRBO
5 Min Walk to Beach | Private Pool | AMI Trolley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience the best of Anna Maria Island from this beautifully appointed 4-bedroom Holmes Beach retreat, featu ...
From $749 per night (USD)VRBO
From $496 per night (USD)Expedia
Sea La Vie - DIRECT BEACH FRONT - by Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the beauty of Anna Maria Island from this elevated beachfront retreat offering stunning panoramic views and u ...
From $496 per night (USD)Expedia
From $370 per night (USD)VRBO
Family-Friendly 3BR - Walk to Beach & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy, newly renovated 3BR/2BA home just a short walk to the quiet shores of Holmes Beach. With spacious bedrooms, a full ...
From $370 per night (USD)VRBO
From $329 per night (USD)Expedia
Sunrays Anchor by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Sunrays Anchor! This cute and cozy updated 2-bedroom, 2 bath two level condo sleeps up to five. This condo is ...
From $329 per night (USD)Expedia
From $480 per night (USD)VRBO
3BR Oceanfront Condo w/ Direct Beach Access & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to our 3B Oceanview Condo with an incredibly large balcony looking right out onto the gulf! Beautiful ...
From $480 per night (USD)VRBO
From $294 per night (USD)Expedia
Sun Plaza West 105 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wake up just steps from the sugar-white sands and sparkling shoreline in this beautifully updated coastal retreat. Perfe ...
From $294 per night (USD)Expedia
From $448 per night (USD)VRBO
2BR Beachfront Condo w/ Oceanview & Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: ✔️ Oceanfront Anna Maria Island 🌴 ✔️ 180° Gulf views 🌊 ✔️ Floor-to-ceiling windows ✔️ Private balcony (4 ...
From $448 per night (USD)VRBO
From $315 per night (USD)Expedia
Flip Flop Inn: Dog Friendly, Pool, 1.5 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flip Flop Inn by Anna Maria Life Vacation Rentals 201 57th, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $315 per night (USD)Expedia
From $305 per night (USD)VRBO
Turtle Tracks: 1 Block to Beach! Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Turtle Tracks by Anna Maria Life Vacation Rentals 7203 Gulf Drive, Holmes Beach, FL 34217 What You'll Love About This H ...
From $305 per night (USD)VRBO
From $1162 per night (USD)Expedia
Midnight Breeze - Brand New Luxury!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Midnight Breeze by Exclusive Vacations, a modern coastal luxury home located just one block from the Gulf in ...
From $1162 per night (USD)Expedia
From $420 per night (USD)VRBO
A Perfect Place: Newly Remodeled Ground Level with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the "Perfect Place" on Anna Maria Island! This newly renovated, ground level, 3 bedroom 3 bath home offers th ...
From $420 per night (USD)VRBO
From $674 per night (USD)Expedia
Pineapple Paradise-Pool Home 2Blocks to the Beach-By Island Real Estate
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Discover your perfect Anna Maria Island vacation rental in Holmes Beach! Brand new to the vacation rental market, this 4 ...
From $674 per night (USD)Expedia
From $327 per night (USD)VRBO
Waterfront home with a dock and heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“A Shore Thing” – Waterfront Pool Home on Anna Maria Island A Shore Thing is exactly that—your perfect place to create ...
From $327 per night (USD)VRBO
From $412 per night (USD)VRBO
TieDyeSky AMI: Private Waterfall Pool, Lanai, Steps 2 Beach, Elevator
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Anna Maria Island Beach House | Family-Friendly | Private Heated Pool | Steps to Beach Looking for the perfect Anna Ma ...
From $412 per night (USD)VRBO
From $554 per night (USD)VRBO
Coastal Livin' by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coastal Livin’ formerly known as Sunsets on Carissa | Holmes Beach Vacation Rental with Private Pool – Walk to the Beach ...
From $554 per night (USD)VRBO
From $212 per night (USD)Expedia
Charming Sea-Side Serenity 2 Beds 2 Baths, steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect beach getaway! Nestled just a short walk from the pristine beaches of Anna Maria Island, this c ...
From $212 per night (USD)Expedia
From $289 per night (USD)VRBO
Nautilus 215 by Nautilus Vacations-Beachfront Complex, Heated Pool, Racket Court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Nautilus! We are 34 individually owned and uniquely decorated condominiums available for vacation rentals ...
From $289 per night (USD)VRBO
From $408 per night (USD)Expedia
Nautilus 209 by Nautilus Vacations - Beachfront Condo, Heated Pool, Racket Court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Nautilus! We are 34 individually owned and uniquely decorated condominiums available for vacation rentals ...
From $408 per night (USD)Expedia
From $594 per night (USD)VRBO
Coastal Pearl | Walk to Beach | Heated Pool + Hot Tub | 4BR Family Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location Highlights • 5-minute walk to the beach – easy access to the famous white sugar sand and turquoise waters of A ...
From $594 per night (USD)VRBO
From $599 per night (USD)Expedia
Beautiful coastal home steps from beach with stunning Gulf views.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this beautiful coastal home, located just steps from the beach with stunning Gulf views. This professionally ...
From $599 per night (USD)Expedia
From $453 per night (USD)VRBO
Sandcastle By The Sea by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A few things that make Sandcastle By The Sea special: Holmes Beach on Anna Maria Island - Short walk to Gulf Beaches Spa ...
From $453 per night (USD)VRBO
From $352 per night (USD)Expedia
Hidden Haven / Private Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Ma ...
From $352 per night (USD)Expedia
From $441 per night (USD)VRBO
Anna Maria Beach House Steps to Sand
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Verde, a charming retreat just steps from Anna Maria Beach. With spacious interiors, multiple comfortabl ...
From $441 per night (USD)VRBO
From $397 per night (USD)Expedia
Palm Gables 112 :NO ELEVATOR Jul 25 - Nov 15, 2026 - Gulf Front Condo, Pool, Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Elevator is out of service from Jul 25 - Nov 15, 2026 Palm Gables 112 by Anna Maria Life Vacation Rentals 112 36th ...
From $397 per night (USD)Expedia
From $404 per night (USD)VRBO
Island Charm by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A few things that make Island Charm special: - Holmes Beach on Anna Maria Island - Short 5 min walk to Gulf Beaches - He ...
From $404 per night (USD)VRBO
From $427 per night (USD)VRBO
Modern Coastal Villa • Steps to Beach + Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Waves On 4th – your modern coastal escape on Anna Maria Island! This stylish 2-bedroom villa is just 1.5 bloc ...
From $427 per night (USD)VRBO
From $348 per night (USD)VRBO
Steps to Beach - Prime Location Beach Bungalow – Beach Gear
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Access Across the Street Welcome to your relaxing beach bungalow steps from the light sand and Caribbean-like wat ...
From $348 per night (USD)VRBO
From $226 per night (USD)Expedia
West Bay Cove 242 · Murphy Bed Office · Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC24-000064 2BR · 2BA · Sleeps 4 · 30-Night Minimum · Pool & Sound Views · Murphy Bed Office · Granite Kitchen · Two H ...
From $226 per night (USD)Expedia
From $308 per night (USD)VRBO
Sunsets & Daydreams – Good Times & Sunshine!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your slice of paradise on Anna Maria Island! Experience coastal charm, modern comfort, and unbeatable locatio ...
From $308 per night (USD)VRBO
From $332 per night (USD)Expedia
Paradise Hideaway- 2 bedrooms condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise Hideaway 3601 East Bay Drive Unit 206, Holmes Beach, FL 34217 What you will love about this property: • Less t ...
From $332 per night (USD)Expedia
From $250 per night (USD)VRBO
Coastal Oasis, Lovely 3-bedroom condo with AC in Holmes Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy a peaceful stay 3 blocks from the beach at this 3-bedroom condo in Holmes Beach. Completely redone, beautiful, bri ...
From $250 per night (USD)VRBO
From $616 per night (USD)Expedia
Glasswater House – Modern Luxury with Infinity Pool & Lake Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Glasswater House, a brand-new luxury retreat where sleek modern design meets peaceful waterfront living. Thou ...
From $616 per night (USD)Expedia
From $583 per night (USD)VRBO
Sea Glass: Beautiful Centrally Located Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away in a serene island setting, this beautifully renovated 3-bedroom, 2-bathroom ground-level home offers the pe ...
From $583 per night (USD)VRBO
From $436 per night (USD)Expedia
New Listing! Sailfish Nest B – Your Island Retreat with Private Pool and Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sailfish Nest B, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a ...
From $436 per night (USD)Expedia
From $395 per night (USD)VRBO
Cozy 2-bedroom condo in charming Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this gorgeous condo in Holmes Beach. With two comfortable bedrooms featuring a king bed and a queen bed, guest ...
From $395 per night (USD)VRBO
From $515 per night (USD)Expedia
Screened Balcony - Griffins' Island Getaway by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $515 per night (USD)Expedia
From $421 per night (USD)VRBO
New Listing Discount! Beautifully renovated home w/pool on canal near beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the serenity of our newly renovated, single-story sanctuary, nestled perfectly alongside an idyllic canal. Th ...
From $421 per night (USD)VRBO
From $424 per night (USD)Expedia
Beach Escape | Heated Pool | Walk to Beach & Golf Cart
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beac ...
From $424 per night (USD)Expedia
From $276 per night (USD)VRBO
Stylish waterfront villa in the heart of Holmes Beach on Anna Maria Island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Seaside 21, your private waterfront retreat on beautiful Anna Maria Island. Nestled in the heart of Holme ...
From $276 per night (USD)VRBO
From $1030 per night (USD)Expedia
Slice of Paradise by Duncan Real Estate
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Slice of Paradise by Duncan Real Estate! Welcome to this stunning custom-built luxury home on Anna Maria Island with fou ...
From $1030 per night (USD)Expedia
From $224 per night (USD)VRBO
Beachside 2BR AMI Villa with Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Beach #4 – AMI Ground-Floor Villa Steps from the Beach & Pool Make your Anna Maria Island vacation unforgett ...
From $224 per night (USD)VRBO
From $468 per night (USD)VRBO
Seaquel: A Tropical Retreat - Private Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan your getaway to the serenity of Seaquel on Anna Maria Island. This 3-bedroom, 2-bathroom detached private pool home ...
From $468 per night (USD)VRBO
From $261 per night (USD)VRBO
Coastal Getaway - Sea Glass Villa by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A few things that make Sea Glass Villa special: 2 Min walk to Beach Community Heated Pool (shared with 3 other units) Pr ...
From $261 per night (USD)VRBO
From $318 per night (USD)Expedia
Ground Floor Luxury 1BR Home · Heated Saltwater Pool & Spa · Very Close to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to AMI Beach Home in Holmes Beach on beautiful Anna Maria Island. This custom-built ground-floor vacation home ...
From $318 per night (USD)Expedia
From $684 per night (USD)VRBO
Casa Morado | Luxury Holmes Beach Retreat with Heated Pool and Hot tub, Steps to Beach I .PET FRIENDLY. ANNA MARIA ISLAND!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Casa Morado, your private slice of paradise on beautiful Anna Maria Island. Located in the heart of Holmes Be ...
From $684 per night (USD)VRBO
From $583 per night (USD)Expedia
Luxury Villa · Heated Saltwater Pool & Spa · Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Prime Location – Steps to the Beach! Luxurious ground-level villa at 124 50th Street, Holmes Beach, in the heart of Anna ...
From $583 per night (USD)Expedia
From $216 per night (USD)VRBO
Private balconies, Walk to Holmes Beach, sleeps 8, access to heated pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this beautifully finished 3-bedroom, 3-bathroom coastal condo, where modern comfort meets Florida charm. Perfe ...
From $216 per night (USD)VRBO
From $602 per night (USD)Expedia
4-bedroom house with Pool and Game Room in Holmes Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the ultimate Florida island retreat at Salty Sands, located just one block from Holmes Beach’s pristine Gulf ...
From $602 per night (USD)Expedia
From $391 per night (USD)VRBO
Bayview Paradise- 3 bedroom canal front
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayview Paradise 518 Bayview Drive, Holmes Beach, FL 34217 What you will love about this property: • Canal front home w ...
From $391 per night (USD)VRBO
From $306 per night (USD)Expedia
Under the Foxtails by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Under the Foxtails, a freshly renovated beach escape offering the perfect blend of comfort, style, and sunshi ...
From $306 per night (USD)Expedia
From $261 per night (USD)VRBO
Beachview 5 · Two Kings · 2-Min Walk to Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000800 2BR · 2BA · Sleeps 4 · Two King Beds · 2-Min Walk to Manatee Beach · Heated Pool · Dual Screened Lanais · ...
From $261 per night (USD)VRBO
From $387 per night (USD)Expedia
Ground Floor Luxury 2BR Home · Heated Saltwater Pool & Spa · Very Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to AMI Beach Home in Holmes Beach on beautiful Anna Maria Island. This custom-built ground-floor vacation home ...
From $387 per night (USD)Expedia
From $378 per night (USD)VRBO
Ground Floor Luxury 3BR Home · Heated Saltwater Pool & Spa · Very Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to AMI Beach Home in Holmes Beach on beautiful Anna Maria Island. This custom-built ground-floor vacation home ...
From $378 per night (USD)VRBO
From $543 per night (USD)Expedia
Gulf Beach Retreat, just steps from the sand of Anna Maria! Private heated pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Beach Retreat is close enough to hear the sound of the waves, smell the salt air, and feel the Gulf breezes calling ...
From $543 per night (USD)Expedia
From $315 per night (USD)VRBO
Chic Holmes Beach #B Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun, Sand & Style at Holmes Beach Relax in this beautifully furnished 3-bedroom, 2.5-bath townhome with a private pool, ...
From $315 per night (USD)VRBO
From $786 per night (USD)Expedia
Walk to Beach | Pool Spa + Mini Golf
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
🌴 WELCOME TO YOUR HOLMES BEACH GETAWAY Just a short walk from the white sands of Anna Maria Island, Sea Glass Harbor i ...
From $786 per night (USD)Expedia
From $419 per night (USD)VRBO
Stunning Beach House with Heated Pool, Spacious Lanai, Just Steps from the Sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Your Dream Beach Escape! One block from the sugar-white sands of Holmes Beach, this freshly renovated coasta ...
From $419 per night (USD)VRBO
From $868 per night (USD)VRBO
New Listing! 400 feet to the beach, Heated pool, Newly remodeled walk to shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Palm Tree Villas is a collection of 8 Villas ranging from Studios to three bedroom Villas. Surrounded by wonderful lands ...
From $868 per night (USD)VRBO
From $418 per night (USD)VRBO
On Ocean Time: 5 Houses to Gulf, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
On Ocean Time by Anna Maria Life Vacation Rentals 112B 79th St, Holmes Beach, FL 34217 What You'll Love About This Home ...
From $418 per night (USD)VRBO
From $569 per night (USD)Expedia
Fairwinds Family Getaway with Pool & Hot Tub - by Island Real Estate Vactions
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Fairwinds, your Anna Maria Island vacation rental where coastal charm meets tropical luxury. This spacious fo ...
From $569 per night (USD)Expedia
From $291 per night (USD)VRBO
Tropical Sunset 4 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tropical Sunset 4, a refreshed and inviting two-bedroom, two-bath retreat just a quick two-minute walk from H ...
From $291 per night (USD)VRBO
From $256 per night (USD)Expedia
Sand & Sun B · EV Charger · Pool · 3 Min Walk To Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC25-000130 1BR · 1BA · Sleeps 2 · EV Charger Included · Sun-Soaked Private Deck · Heated Pool with Covered Shade Sect ...
From $256 per night (USD)Expedia
From $276 per night (USD)VRBO
Sand & Sun A · EV Charger · Pool · 3 Min Walk To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
VRC25-000129 2BR · 2BA · Sleeps 5 · EV Charger Included · Heated Pool with Covered Shade Section · 5-Min to Beach · Twi ...
From $276 per night (USD)VRBO
From $544 per night (USD)Expedia
Top-Floor Gulf Shores Unit 205 w/ Sunset Balcony-By Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wake up to the sound of gentle waves and end every evening with a breathtaking Gulf sunset at this stunning beachfront c ...
From $544 per night (USD)Expedia
From $273 per night (USD)VRBO
Barefoot Bungalow by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Barefoot Bungalow, where you can make yourself at home in this cozy, family-friendly, and pet-friendly space. ...
From $273 per night (USD)VRBO
From $410 per night (USD)Expedia
White Sands Beach House- 4 bedrooms with elevator, pool and close to beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
White Sands Beach House 7005 Holmes Blvd, Holmes Beach, FL 34217 VRC22-000225 What you will love about this property: • ...
From $410 per night (USD)Expedia
From $467 per night (USD)VRBO
Saltwater Bliss by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Saltwater Bliss, a spacious, beautifully updated ground-floor home with room for everyone to relax, gather, a ...
From $467 per night (USD)VRBO
From $377 per night (USD)Expedia
Saltwater Heaven by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Saltwater Heaven, a beautifully refreshed ground-floor retreat with generous room to relax and gather. Just a ...
From $377 per night (USD)Expedia
From $348 per night (USD)VRBO
Canal-Front 3BR Pool Home on Anna Maria Island | 30+ Night Stays
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VRC number VRC25-000143. Top Reasons to Book: - Pet-Friendly (Under 50 lbs, Fee Applies) - Heated Private Pool with Lou ...
From $348 per night (USD)VRBO
From $325 per night (USD)Expedia
Misty Beach, hosted by Beach Retreats on AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Misty Beach | Holmes Beach, Anna Maria Island 2 Bedrooms · 2 Bathrooms · Sleeps 6 Pet Friendly - One dog up to 25 pounds ...
From $325 per night (USD)Expedia
From $331 per night (USD)VRBO
Palm Breeze - 3 Bedroom Mins from Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Breeze by Anna Maria Vacations Welcome to Palm Breeze, a charming three-bedroom, two-bathroom Holmes Beach vacatio ...
From $331 per night (USD)VRBO
From $226 per night (USD)Expedia
Coastal Villa! Lanai, Decks and Pool Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Tropical Villa by Anna Maria Vacations Condo in Holmes Beach, Florida VRC19-000249 Welcome to Island Tropical ...
From $226 per night (USD)Expedia
From $246 per night (USD)VRBO
Pets Stay Free, Heated Pool, 1.5 blk from Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3BR/2BA Holmes Getaway | Sleeps 6 | 1.5 Blocks to Beach Holmes Getaway sits on the upper level of a peaceful duplex in ...
From $246 per night (USD)VRBO
From $362 per night (USD)Expedia
Ilha Bella-Private pool in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ilha Bela by Anna Maria Vacations Home in Holmes Beach, Florida Welcome to Ilha Bela, a timeless three-bedroom, two an ...
From $362 per night (USD)Expedia
From $281 per night (USD)VRBO
Sea Salt & Sunny Days: Pool, Spa, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Salt & Sunny Days by Anna Maria Life Vacation Rentals 205 Haverkos, Holmes Beach, FL 34217 What You'll Love About T ...
From $281 per night (USD)VRBO
From $391 per night (USD)Expedia
Steps to Manatee Beach, Pool, and Private Sun Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax and unwind in this beautiful 2-bedroom, 2-bath duplex featuring a fully equipped kitchen, private sun deck, shared ...
From $391 per night (USD)Expedia
From $436 per night (USD)VRBO
Anna Maria Island Duplex: Pool, Kitchen, Sun Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to your Anna Maria Island getaway in this stylish duplex featuring 2 bedrooms, 2 bathrooms, a fully equipped kitc ...
From $436 per night (USD)VRBO
From $533 per night (USD)Expedia
Anna Maria Beach House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Vrc16-000901 Anna Maria Beach House | Beach House Rental on Anna Maria Island | Steps to the Beach Welcome to Anna Mar ...
From $533 per night (USD)Expedia
From $227 per night (USD)VRBO
Terrific 2-bedroom house 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 $227 per night (USD)VRBO
From $250 per night (USD)Expedia
Nautilus 103 by Nautilus Vacations-Beachfront Complex, Heated Pool, Racket Court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Nautilus 103! VRC25-000019 We are 34 individually owned and uniquely decorated condominiums available for ...
From $250 per night (USD)Expedia
From $706 per night (USD)VRBO
It's Miller Time by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A few things that make It's Miller Time special: Concierge Collection Property Golf cart included! Holmes Beach on Anna ...
From $706 per night (USD)VRBO
From $419 per night (USD)Expedia
Perfect Coastal Getaway by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect coastal getaway on beautiful Holmes Beach, just one block from the shimmering Gulf of Mexico wit ...
From $419 per night (USD)Expedia
From $252 per night (USD)VRBO
Tiffany Place 114 ~Holmes Beach~Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachfront 2BR/2BA Condo | 50 Steps to Gulf | Holmes Beach, Anna Maria Island, FL | Sleeps 4 Experience coastal luxury ...
From $252 per night (USD)VRBO
From $769 per night (USD)Expedia
Spacious Beachfront Home in Holmes Beach on Anna Maria Island! Swell Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stay comfortably in Holmes Beach at this 4-bedroom house less than 100 steps to the beach-no streets to cross! Guests wi ...
From $769 per night (USD)Expedia
From $344 per night (USD)VRBO
By the Bay - Bayfront Home w/ Private Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect island escape in the exclusive Key Royale community on Anna Maria Island! This beautifully renov ...
From $344 per night (USD)VRBO
From $423 per night (USD)Expedia
Still Waters hosted by Beach Retreats FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Still Waters | Holmes Beach, Anna Maria Island 3 Bedrooms · 2.5 Bathrooms · Sleeps 6 · License VRC16-000609 Two minutes ...
From $423 per night (USD)Expedia
From $417 per night (USD)VRBO
Flamingo Fling - Pool, Hot Tub & Putting Fun!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Flamingo Fling by Coastal Chic Vacations! - Steps to Anna Maria Island's white sandy beaches - Private heate ...
From $417 per night (USD)VRBO
From $249 per night (USD)Expedia
Close to beach w/ direct beach access, private fenced yard, Games and beach gear
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the heart of Holmes Beach West of Gulf Drive with direct beach access at the end of the street and many great ...
From $249 per night (USD)Expedia
From $168 per night (USD)VRBO
Cute and Cozy Island Bungalow, newly remodeled and a short walk to the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
New to our rental inventory and awaiting your review! Welcome to the charming Starfish at 211 77th St East Unit, a cozy ...
From $168 per night (USD)VRBO
From $614 per night (USD)Expedia
Black Pearl! NEW! Block and half to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Black Pearl is a brand-new luxury 4-bedroom, 4-bath home just a block and a half from the beaches of Holmes Be ...
From $614 per night (USD)Expedia
From $224 per night (USD)VRBO
Mangrove Cove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Cove at Sandy Pointe. This bayside 2-bedroom, 2-bathroom condo is nestled in the most serene, mangrove-li ...
From $224 per night (USD)VRBO
From $640 per night (USD)Expedia
White Pearl - Pool/Rooftop/Mini Golf!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Luxury island retreat featuring 4 bedrooms plus an office with sleeper sofa, private pool, spa, putting green, ...
From $640 per night (USD)Expedia