Holmes Beach, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Holmes Beach, Florida on RentalSaver.com!

Holmes Beach Rentals

From $466 per night (USD)
VRBO
La Casa AMI Beachside-Beachfront Condo w/ Heated Pool, Hot tub & Garage Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spend a week in paradise at La Casa Costiera, one of Anna Maria Island’s most exclusive beachfront communities. This spa ...
From $466 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Experience Kismet by the Sea: Chic Holmes Beach Rental with Shared Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kismet by the Sea by AMI Locals Experience your perfect island escape at Kismet by the Sea, a charming three-bedroom, ...
From $233 per night (USD)
Expedia
From $786 per night (USD)
VRBO
Golf Cart - Beachy Keen by SeaBreeze Vacation
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to Beachy Keen, your dream getaway on beautiful Anna Maria ...
From $786 per night (USD)
VRBO
From $846 per night (USD)
Expedia
Cocktails and Dreams by Beach Boutique Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to Cocktails and Dreams, a stylish island retreat with a private pool, spa, and a prime location just moments fro ...
From $846 per night (USD)
Expedia
From $1208 per night (USD)
VRBO
2 Min Walk to Beach, Bikes, Paddleboards, Heated Pool, Hot Tub, Fireplace
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
We invite you to discover an elevated escape to Anna Maria Island at our brand new luxury home Royal Palms. Located only ...
From $1208 per night (USD)
VRBO
From $1158 per night (USD)
Expedia
Anna Maria Wave: Stunning Beachfront Home with Pool and Poker Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Anna Maria Wave by Anna Maria Island Accommodations Welcome to Anna Maria Wave by Anna Maria Island Accommodations, a ...
From $1158 per night (USD)
Expedia
From $518 per night (USD)
VRBO
AMI Beachfront Condo Gulf Views, Heated Pool, 3BR at Gulf Place Great Sunsets!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the ultimate coastal retreat at Gulf Place 18, a beautifully appointed three-bedroom, two-bath condominium on ...
From $518 per night (USD)
VRBO
From $636 per night (USD)
Expedia
A Villa by the Sea - L'Plage #4 - 3-bedroom Beachfront condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A Villa by the Sea - L'Plage #4 6404 Gulf Drive, Holmes Beach 34217 VRC19-000240 What you will love about this property: ...
From $636 per night (USD)
Expedia
From $512 per night (USD)
VRBO
La Isla Bonita by Coastal Chic Vacations
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to La Isla Bonita! - Steps to Anna Maria Island's powdery-white sandy beaches - Private heated pool, ping pong ...
From $512 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Location! Family Friendly, Pool, Elevator, Close to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your Holmes Beach getaway in the heart of Anna Maria Island. This bright, modern home offers a clean, comfort ...
From $472 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Spacious 3,000+ resort style home •Huge lagoon pool, hot tub -Room for everyone🌴
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your perfect Anna Maria Island getaway. This beautifully remodeled, SPACIOUS single-level coastal home is des ...
From $432 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Pool Heated & Private, Close to Beach, Luxury Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Make memories steps from Anna Maria’s sugar-sand shore. Enjoy your own heated pool, modern chef’s kitchen and soaring 11 ...
From $265 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Beautiful Spacious 4 Bdrm 2nd floor Condo! Heated Pool and Steps to the beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Amazing location! Newly renovated - Steps to the Beach! Spacious 4 bedroom/2 bathroom - 2nd floor Condo accessible only ...
From $672 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Low Rates for longer stays! Perfect Location! Steps to Beach!/Heated pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated & furnished! Steps to the Beach! 1 Bdrm 1 bath Condo - shared heated pool Island Life Suites is centra ...
From $332 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Sea Haven:Family home steps to beach, pool, hot tub, Foosball, putting green!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Photos Updated March 2025! Welcome to Sea Haven, a spacious and inviting 5-bedroom, 4.5-bathroom home just three houses ...
From $724 per night (USD)
VRBO
From $1090 per night (USD)
Expedia
Tiki By The Sea by Duncan Real Estate
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Tiki by the Sea! This beautiful, centrally located 5-bedroom, 3-bathroom pool home has 1,921 under A/C square ...
From $1090 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Island Time - 2 Minute Walk To The Beach & Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom two bathroom condo just steps to the beach! The living and dining areas open on to a screened lanai with po ...
From $353 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Best Little Beach House on Anna Maria Island! With a pool & steps to the beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is the Best Little Beach House on Anna Maria Island...with a pool. Make yourself at home in this welcoming 1-bedro ...
From $404 per night (USD)
Expedia
From $249 per night (USD)
VRBO
⚓Hidden Treasure Unit A! Heated Pool just 200 steps to the beach!⚓
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Hidden Treasure Unit A! VRC18-000124 ⚓ .1 Miles to Holmes Beach ...
From $249 per night (USD)
VRBO
From $235 per night (USD)
Expedia
⚓Hidden Treasure Unit B! Heated Pool just 200 steps to the beach!⚓
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Hidden Treasure Unit B! VRC25-000106 ⚓ .1 Miles to Holmes Beach ⚓ Shared Heated Pool ⚓Walk to Manatee ...
From $235 per night (USD)
Expedia
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VRBO
Luxury Beach Home•Steps to Beach•Excellent Location•Sunsets
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Experience Anna Maria Island at 203 By The Sea. Just a block from the beach, this beautifully designed home offers the p ...
Click For Pricing
VRBO
From $1627 per night (USD)
Expedia
Swanky Bubbles- Luxury 9 bedroom close to beach with views, pool and spa!!!
Bedrooms:
10
Bathrooms:
9
Sleeps:
18
Swanky Bubbles 6506 Gulf Drive, Holmes Beach, FL 3421 VRC22-000202 What you will love about this property: • Luxury home ...
From $1627 per night (USD)
Expedia
From $397 per night (USD)
VRBO
3 Blocks to Beach ☀️ Game room, cabana bar + family fun
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Just 3 blocks to the beach & steps to the canals! Bring the whole crew to this bright & breezy 3-bed, 3 bath beach house ...
From $397 per night (USD)
VRBO
From $325 per night (USD)
Expedia
⚓Mermaid Sunset! Coastal beach home w/pool 200 steps to beach!⚓
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Mermaid Sunset! VRC16-000276 ⚓Private Heated Pool/ Spa ⚓200 steps to Holmes Beach ⚓Beach Chairs & Wagon Ava ...
From $325 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Fanta Sea | Pool, Hot Tub, Game Room & 7 Minute Walk to the Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Get ready for laid-back luxury! This fun and breezy 4-bedroom, 2.5-bath Holmes Beach retreat has everything you need for ...
From $515 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Walk to Gulf: Luxe Luau-Themed Gem in Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly Remodeled | 7-Night Min Stay | Al Fresco Dining | BBQ Ready Enjoy a one-of-a-kind stay in the Sunshine State at t ...
From $558 per night (USD)
Expedia
From $489 per night (USD)
VRBO
WatersEdge208DIRECT GULFFRONT Pool & Tennis – By Island Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Water’s Edge 208S – Your perfect island escape on Anna Maria Island. Located just steps from the sparkling Gu ...
From $489 per night (USD)
VRBO
From $1054 per night (USD)
Expedia
Blue Oasis Retreat: 2 Pools & Spas | 5-Min Walk to Beach | Sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Blue Oasis Retreat by AMI Locals VRC18-000117 Welcome to Blue Oasis Retreat, a gorgeous duplex just a five-minute str ...
From $1054 per night (USD)
Expedia
From $1116 per night (USD)
VRBO
Two Houses from Beach! Rooftop, Pool & Game Room
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Salty Margarita by AMI Locals Welcome to Salty Margarita, a stunning three-level coastal retreat just two houses from t ...
From $1116 per night (USD)
VRBO
From $867 per night (USD)
Expedia
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)
Expedia
From $544 per night (USD)
VRBO
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)
VRBO
From $284 per night (USD)
Expedia
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)
Expedia
From $369 per night (USD)
VRBO
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)
VRBO
From $441 per night (USD)
Expedia
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)
Expedia
From $202 per night (USD)
VRBO
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)
VRBO
From $385 per night (USD)
Expedia
Honu Hale: Enjoy your tropical getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Honu Hale by Anna Maria Island Accommodations Welcome to Honu Hale by Anna Maria Island Accommodations, a newly renova ...
From $385 per night (USD)
Expedia
From $663 per night (USD)
VRBO
Twin Tides, 2 Kitchens! Pool, Spa, Golf Cart, Putting Green, Tiki Bar, Sleeps 14
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Enjoy this newly renovated, serene island retreat. Spanning 3,600 square feet, this stunning home is one of the largest ...
From $663 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Gulf View Getaway | Sand & Sunset Views Daily!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Gulf View Getaway, your relaxing island retreat where breathtaking Gulf views and unforgettable beachside mem ...
From $295 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Summary: 🍍 Pineapple Paradise is a 4BR/6.5BA luxury home just steps from the beach, perfect for families and groups ☀️ ...
From $750 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Gulf Breeze
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Vrc25-000069 Welcome to Gulf Breeze – Your Island Retreat in Holmes Beach Looking for your perfect island escape? Gulf ...
From $435 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Sandy Pointe 202 - 2BR Island Dog Friendly Condo - by Island Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise at Sandy Pointe 202, a bright and breezy 2-bedroom, 2-bathroom condo located on the second floor in t ...
From $198 per night (USD)
VRBO
From $914 per night (USD)
Expedia
Spacious 4BR Beach Home w/ Private Pool & Spa, Steps to Sand, Sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Salty Shamrock, now proudly managed by Adored Luxe Getaways. This 5-star retreat blends coastal design with t ...
From $914 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Island Vibe 7
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
<p>Welcome to Island Vibe 7, a newly renovated ground-level, 4-bedroom, 3-bathroom single-family home with a private, he ...
From $417 per night (USD)
VRBO
From $234 per night (USD)
Expedia
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)
Expedia
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 $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
Click For Pricing
VRBO
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 Pricing
VRBO
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 $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
Click For Pricing
VRBO
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 Pricing
VRBO
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 $285 per night (USD)
VRBO
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)
VRBO
From $665 per night (USD)
Expedia
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)
Expedia
From $546 per night (USD)
VRBO
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)
VRBO
From $658 per night (USD)
Expedia
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)
Expedia
From $385 per night (USD)
VRBO
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)
VRBO
From $409 per night (USD)
Expedia
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)
Expedia
From $532 per night (USD)
VRBO
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)
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 $228 per night (USD)
VRBO
Snowbird Paradise | Monthly Beachfront Condo with Lanai, Pool & Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Martinique Cheer, your cheerful beachside escape on beautiful Anna Maria Island! This rare higher-rise Holmes ...
From $228 per night (USD)
VRBO
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 $335 per night (USD)
VRBO
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)
VRBO
From $303 per night (USD)
Expedia
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)
Expedia
From $438 per night (USD)
VRBO
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)
VRBO
From $294 per night (USD)
Expedia
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)
Expedia
From $562 per night (USD)
VRBO
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)
VRBO
From $313 per night (USD)
Expedia
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)
Expedia
From $313 per night (USD)
VRBO
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)
VRBO
From $576 per night (USD)
Expedia
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)
Expedia
From $608 per night (USD)
VRBO
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)
VRBO
From $638 per night (USD)
Expedia
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)
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

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