Holmes Beach Rentals
From $867 per night (USD)VRBO
Luxury 3BD Beachfront Retreat with Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. ...
From $867 per night (USD)VRBO
From $544 per night (USD)Expedia
Fancy That: Pool, Putting Green, 1.5 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
209 77th St, Holmes Beach, FL 34217 What You'll Love About This Home: Ideal Location! 1.5 Blocks to the Beach! 3 Bedroo ...
From $544 per night (USD)Expedia
From $284 per night (USD)VRBO
Palm Isle Village 3208 - Charming Beachside Condo | Island Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Disclaimer: Discoloration in the pool is from staining, not dirt or debris. The pool is safe and clean for swimming. Ac ...
From $284 per night (USD)VRBO
From $369 per night (USD)Expedia
Beachfront Gulf Views 2BR 2BA with pool and elevator -just steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Relax in Comfort at Your Beachside Getaway! Welcome to your cozy coastal retreat! This beautiful two-bedroom, two-bathro ...
From $369 per night (USD)Expedia
From $441 per night (USD)VRBO
83rd St Villas West by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 83rd St Villas West! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bed ...
From $441 per night (USD)VRBO
From $202 per night (USD)Expedia
Beachfront Balcony, Cozy Escape
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Mermaid’s Retreat by Anna Maria Island Accommodations Welcome to Mermaid’s Retreat, a bright and inviting two-bedroom ...
From $202 per night (USD)Expedia
From $234 per night (USD)VRBO
3-bedroom North Beach Village paradise, 5 minute walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to gorgeous Anna Maria Island and enjoy all it has to offer. Nestled in Holmes Beach, this delightful townhome ha ...
From $234 per night (USD)VRBO
From $405 per night (USD)VRBO
Luxurious beachfront condo, gorgeous top-floor Gulf views, with heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our 2-bedroom, 2-bath, beachfront condo on Anna Maria Island is perfect for your dream escape to a tropical paradise. Un ...
From $405 per night (USD)VRBO
From $524 per night (USD)VRBO
LivingGood by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy vacation bliss at this completely remodeled island pool home called LivinGood! The house features the perfect blen ...
From $524 per night (USD)VRBO
From $168 per night (USD)Expedia
Seabreeze Sanctuary: 2BR/2BA Waterfront Condo - Stunning Views & Prime Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax in this bright 2BR/2BA condo with stunning bay views in the sought-after Westbay Point & Moorings community. Enjoy ...
From $168 per night (USD)Expedia
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Charming Anna Maria Island Condo - Short Walk To The Beach - Shell Yeah
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Shell Yeah! Professionally managed by Gulf Coast Vacation Rentals, this stunning 3-story townhouse is located ...
Click For PricingVRBO
From $379 per night (USD)Expedia
Beachfront Escape at Martinique South: 2BR/2BA Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
***RESERVATIONS MUST BE MADE AT LEAST 30-DAYS PRIOR TO CHECK-IN*** Soak in breathtaking views of the Gulf of Mexico fro ...
From $379 per night (USD)Expedia
From $644 per night (USD)VRBO
Beautiful Beach house! Heated pool and spa!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning ...
From $644 per night (USD)VRBO
From $791 per night (USD)Expedia
Thanksgiving availability! Stunning pool home!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to The Colony, a stunning vacation rental on Anna Maria Island, designed to capture the essence of Pal ...
From $791 per night (USD)Expedia
From $321 per night (USD)VRBO
Cozy Beach Cottage, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Charming 3bed/2bath, pet friendly beach cottage in the PERFECT LOCATION! Just 1 block to the beach. This impec ...
From $321 per night (USD)VRBO
From $673 per night (USD)VRBO
Two Bedroom Modern Island Villa w/ Kitchen Near Pine Avenue Shops & Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $673 per night (USD)VRBO
From $784 per night (USD)VRBO
Stylish, Boutique, Two-Bedroom Villa with Fully-Equipped Kitchen and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $784 per night (USD)VRBO
From $727 per night (USD)VRBO
Two-Bedroom Modern Island Villa with Gourmet Kitchen, Balcony and Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $727 per night (USD)VRBO
From $681 per night (USD)VRBO
Resort-Style Villa with Kitchen, Balcony and Pool Near AMI Gulf Waters & Trails
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $681 per night (USD)VRBO
From $727 per night (USD)VRBO
Two-Bedroom Villa w/ Balcony and Pool Near AMI Sunset Spots & Kayak Launch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $727 per night (USD)VRBO
From $784 per night (USD)VRBO
Two-Bedroom Villa with Tranquil Colors, Soothing Textures and Island Charm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind on Anna Maria Island—pristine beaches, turquoise Gulf waters, and iconic piers just minutes away. Stroll Bridge S ...
From $784 per night (USD)VRBO
From $400 per night (USD)Expedia
Coastal 2BR/2BA w/ Heated Pool + 200 Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌴 Seacrest AMI | 2BR w/ Saltwater Pool | Central Location 📍207 71st Street Holmes Beach Welcome to Seacrest AMI, your ...
From $400 per night (USD)Expedia
From $317 per night (USD)VRBO
Pet Friendly 3BR W/ Tropical Views, Porch & Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Top Reasons to Book: - Prime Holmes Beach location, short stroll to the Gulf - Heated community pool on-site - Pet Frien ...
From $317 per night (USD)VRBO
From $578 per night (USD)Expedia
Beachside Condo, Anna Maria FL, King Bed 2nd Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to our beachy one-bedroom apartment, perfect for families seeking a relaxing getaway on beautiful Holme ...
From $578 per night (USD)Expedia
From $425 per night (USD)VRBO
Beachfront Condo | Anna Maria FL | Unit 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to our beachy one-bedroom apartment, perfect for families seeking a relaxing getaway on beautiful Holme ...
From $425 per night (USD)VRBO
From $578 per night (USD)Expedia
Beachside Condo, Anna Maria FL, King Bed 2nd Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to our beachy one-bedroom apartment, perfect for families seeking a relaxing getaway on beautiful Holme ...
From $578 per night (USD)Expedia
From $564 per night (USD)VRBO
Beachside Condo, Anna Maria FL, King Bed 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to our beachy one-bedroom apartment, perfect for families seeking a relaxing getaway on beautiful Holme ...
From $564 per night (USD)VRBO
From $351 per night (USD)Expedia
Southern Cross: 3 Min Walk to Gulf Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Southern Cross, a charming coastal cottage in the heart of Anna Maria Island. Just a 3-minute stroll from the ...
From $351 per night (USD)Expedia
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February & March Special: Luxury Canal Home with Pool & Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Woodside Beach House, a luxury waterfront retreat in the heart of Holmes Beach. Designed with comfort and ele ...
Click For PricingVRBO
From $428 per night (USD)Expedia
Blue Haven Beach House: 3BR/3BA Pool Home Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Haven Beach House is a beautifully updated, elevated home located in the heart of Holmes Beach—just steps from the ...
From $428 per night (USD)Expedia
From $446 per night (USD)VRBO
North Beach Village #62 by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to North Beach Village #62 - a 3BD/2.5BA Key West style townhouse on Holmes Beach! It's located in a quiet and ...
From $446 per night (USD)VRBO
From $285 per night (USD)Expedia
Palm Cay 2: 3 Min Walk to Beach and Shared Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Palm Cay 2 by Anna Maria Island Accommodations Welcome to Palm Cay 2, a charming 2-bedroom, 2-bath vacation condo locat ...
From $285 per night (USD)Expedia
From $665 per night (USD)VRBO
Blue Tides by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Your dream waterfront escape awaits in this fully remodeled 3-bedroom canal-front retreat. *Features include* * Compl ...
From $665 per night (USD)VRBO
From $546 per night (USD)Expedia
Heated Pool, Hot Tub, Game Room, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Dreams, which just completed a FULL renovation! *NOTE* Holmes Beach requires 7-day minimum rentals, ...
From $546 per night (USD)Expedia
From $658 per night (USD)VRBO
2-Min walk to beach, Pool, Hot Tub, Putting Green!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the ultimate Florida getaway at #WeekendSuits, an exceptional 4-bedroom, 3.5-bath retreat nestled in the hear ...
From $658 per night (USD)VRBO
From $385 per night (USD)Expedia
Private Pergola Oasis. Walk to Beach, Shop & Dine
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sa ...
From $385 per night (USD)Expedia
From $409 per night (USD)VRBO
Enjoyable 6 Minute Walk to Beach and Heated Saltwater Pool for ONLY Your Family.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This immaculately clean 2-bedroom condo (side B) in Holmes Beach is perfect for your vacay. With 2 queen beds and 2 full ...
From $409 per night (USD)VRBO
From $532 per night (USD)Expedia
By the Sand cozy 3 story house Steps from the Sand of Holmes Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in Holmes Beach, this delightful 3 story house offers 3 nice bedrooms, 2 bathrooms, and a range of fabulous amen ...
From $532 per night (USD)Expedia
From $392 per night (USD)VRBO
3BR Beach Home heated Pool, Decks & BBQ
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Step into your island retreat at this bright three-bedroom, two-bath home in the heart of Holmes Beach. Relax in the ope ...
From $392 per night (USD)VRBO
From $200 per night (USD)Expedia
Flip Floppin' at Sandy Pointe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights: - Short walk to the beach - Accommodates up to 4 guests - 2 king beds - Private screened balcony - ...
From $200 per night (USD)Expedia
From $310 per night (USD)VRBO
Nautilus 214 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 $310 per night (USD)VRBO
From $307 per night (USD)Expedia
Low Tide Beach House on AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Highlights: • Four-minute walk to powdery white sand beaches • 2 bedrooms, 2 bathrooms (plus pullout sofa in living room ...
From $307 per night (USD)Expedia
From $272 per night (USD)VRBO
Walk To Beach | Heated Lagoon Pool, on Anna Maria!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Anna Maria Island and enjoy your own private heated lagoon-style pool, tropical backyard, and an easy five-min ...
From $272 per night (USD)VRBO
From $204 per night (USD)Expedia
The Pink Haven in Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Pink Haven, a beautifully renovated coastal retreat nestled in the heart of Holmes Beach on Anna Maria Is ...
From $204 per night (USD)Expedia
From $503 per night (USD)VRBO
Lake by the Beach by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Lake by the Beach!This newly renovated and updated, lakeside family home in Holmes Beach, an easy walk to the ...
From $503 per night (USD)VRBO
From $335 per night (USD)Expedia
The Blue Haven: Ground level 2 BR with private pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Blue Haven, your private island retreat in the heart of Holmes Beach. This beautifully updated 2-bedroom, ...
From $335 per night (USD)Expedia
From $303 per night (USD)VRBO
1 Block to Beach | Garage Game Room | Community Pool | Beach Gear | Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
KEY FEATURES: ☀ Everything You Need for a Perfect Beach Day Chairs, toys, cooler, wagon, umbrella — just bring your swi ...
From $303 per night (USD)VRBO
From $438 per night (USD)Expedia
Pool - The Sea Pearl by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Just a block and a half from the beach, this bright and airy elevated pool home offers the perfect blend of relaxation, ...
From $438 per night (USD)Expedia
From $294 per night (USD)VRBO
Gone Coastal Fountainhead 2 - Townhome Anna Maria by Island Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Gone Coastal awaits the vacationer in you! Located in a well-kept condo complex directly across the street from the best ...
From $294 per night (USD)VRBO
From $562 per night (USD)Expedia
Lakefront · Fishing · Heated Pool · Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Haven is a remodeled 3BR/3BA lake-front home in Holmes Beach, about a five-minute walk to the sand. Fish right off t ...
From $562 per night (USD)Expedia
From $313 per night (USD)VRBO
Island Bay House A in Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Bay House Unit A, a three-bedroom, two-bath waterfront duplex vacation rental in Holmes Beach. Located ...
From $313 per night (USD)VRBO
From $313 per night (USD)Expedia
Island Bay House B in Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Bay House Unit B, a three-bedroom, two-bath waterfront vacation rental in Holmes Beach. Located on the ...
From $313 per night (USD)Expedia
From $576 per night (USD)VRBO
Top-Floor Gulf Front · Sunset Balcony · Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts 109 is a top-floor, Gulf-front one-bedroom on the beach in Holmes Beach. Water views from the kitchen, living r ...
From $576 per night (USD)VRBO
From $608 per night (USD)Expedia
Beachfront · Heated Pool · Screened Patio on Sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts 105 is a ground-floor, Gulf-front one-bedroom on Anna Maria Island. Slide open the doors, cross the screened pa ...
From $608 per night (USD)Expedia
From $638 per night (USD)VRBO
Beachfront · Heated Pool · Steps to the Sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts 106 is a renovated ground-floor beachfront one-bedroom on Holmes Beach. Open the back slider, cross the screene ...
From $638 per night (USD)VRBO
From $165 per night (USD)Expedia
Walk to Beach, Dining & Shops- Community Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to a relaxing coastal retreat where comfort, convenience, and laid-back beach vibes come together, just a few wal ...
From $165 per night (USD)Expedia
From $389 per night (USD)VRBO
Condo 3 Bedroom /2.5 Bath, maximum occupancy of 6 people. Vrc26-000021
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 6
Condo 3 Bedroom /2.5 Bath, maximum occupancy of 6 people. Vrc26-000021 Community pool, bright, breezy and impeccably la ...
From $389 per night (USD)VRBO
From $502 per night (USD)Expedia
Island Escape- 4 bedrooms with private pool and spa!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Escape 313 B 58th Street, Holmes Beach, FL 34217 What you will love about this property: • Less than 7-minute wal ...
From $502 per night (USD)Expedia
From $258 per night (USD)VRBO
Nautilus 205 by Nautilus Vacations-Beachfront Complex, 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 $258 per night (USD)VRBO
From $640 per night (USD)Expedia
Coastal Paradise- Brand new 4 bedroom with rooftop elevator
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Coastal Paradise 2918 Gulf Drive, Holmes Beach, FL 34217 What you will love about this property: • Less than 2- minute ...
From $640 per night (USD)Expedia
From $413 per night (USD)VRBO
Large Beachfront 3B Condo | Heated Pool & Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: La Casa Beachfront Condo on Holmes Beach, Anna Maria Island. This spacious 2,300+ sq ft, 3-bedroom, 1.5-bath r ...
From $413 per night (USD)VRBO
From $454 per night (USD)VRBO
Steps to Beach, Shared Heated Pool, 4 Decks, Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Escape to North Gulf Villa, a spacious 3-bedroom, 2-bath townhome on the north end of Anna Maria Island, just ...
From $454 per night (USD)VRBO
From $591 per night (USD)VRBO
Silver Surf- A stunning family home 2 blocks from the beach.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $591 per night (USD)VRBO
From $175 per night (USD)Expedia
2BR/2BA AMI Gem, Bay Views, Pool & Pickleball, Short Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Holmes Beach, enjoy what this 2-bedroom condo has to offer. Each bedroom features a comfortable king bed, pro ...
From $175 per night (USD)Expedia
From $262 per night (USD)VRBO
Anna Maria Island 2-bed, 2-bath waterfront in West Bay Cove.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Anna Maria Island Rental These are your 100,000.00 views These are views from the master bedroom, living room, kitchen, ...
From $262 per night (USD)VRBO
From $323 per night (USD)Expedia
Tides & Turtles · Canal Dock · Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VRC21-000151 2BR · 2.5BA · Sleeps 6 · 2025 Renovation · Private Dock · Direct Canal Access · Covered Patio · Quartz Kit ...
From $323 per night (USD)Expedia
From $249 per night (USD)VRBO
Endless Summer • Newly Renovated Hidden Gem in the Heart of AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your Anna Maria Island getaway – a bright, newly renovated coastal retreat tucked along a quiet residential s ...
From $249 per night (USD)VRBO
From $1188 per night (USD)Expedia
Brand NEW! Beach house - 100 yards from Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Brand-New 2026 Luxury Home | 4 Bedrooms | 4.5 Bathrooms | Prime Location 4 Bedrooms – Each with a private bathroom Loc ...
From $1188 per night (USD)Expedia
From $188 per night (USD)VRBO
Steps to the beach - King Master Suite and Beach Path!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical paradise, just steps to the beach! This beautifully remodeled beach bungalow is completely new and full of amen ...
From $188 per night (USD)VRBO
From $591 per night (USD)Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $591 per night (USD)Expedia
From $220 per night (USD)VRBO
Wake Up to Waves – King Master Suite & Beach Path
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical paradise, just steps to the beach! This beautifully remodeled 3/2 bungalow is completely new and full of amenit ...
From $220 per night (USD)VRBO
From $406 per night (USD)Expedia
Nautilus 207 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 $406 per night (USD)Expedia
From $258 per night (USD)VRBO
Salt & Surf Cottage - Charming 2-bed house on Anna Maria Island w/ putting green
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Salt & Surf Cottage, your relaxing island escape in the heart of Holmes Beach! Perfectly situated across the ...
From $258 per night (USD)VRBO
From $240 per night (USD)VRBO
Island Vibe 5: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Vibe 5 a newly renovated 2-bedroom, 2-bathroom pool home. This beautiful property will sleep 6 people ...
From $240 per night (USD)VRBO
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 $358 per night (USD)VRBO
Waters Edge - Anna Maria Island - 1 bedroom 1 and 1/2 bath gulf-front condo - Maximum Occupancy 4 people.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Waters Edge - Anna Maria Island - 1 bedroom 1 and 1/2 bath gulf-front condo - Maximum Occupancy 4 people. Vrc26-000016 ...
From $358 per night (USD)VRBO
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)VRBO
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)VRBO
From $749 per night (USD)Expedia
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)Expedia
From $496 per night (USD)VRBO
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)VRBO
From $370 per night (USD)Expedia
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)Expedia
From $329 per night (USD)VRBO
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)VRBO
From $480 per night (USD)Expedia
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)Expedia
From $193 per night (USD)VRBO
Anna Maria Island -walk to the beach, shops and restaurants!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New Paint, Furniture and Decor as part of our mini makeover! King in primary bedroom and queen in second bedroom! Whe ...
From $193 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 $1165 per night (USD)VRBO
Lůum at the Shore - A Bali-Inspired Luxury Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Lůum at the Shore — a Bali-inspired coastal sanctuary designed to help you restore and reconnect. Thoughtfull ...
From $1165 per night (USD)VRBO
From $554 per night (USD)Expedia
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)Expedia