
Holmes Beach Rentals

- From $445 per night (USD)
VRBO
Island West Villa! Pool, BBQ & Walk to Sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Villa #5 Seashell at Island West Resort by AMI Locals Holmes Beach Villa with Shared Pool Your dream beach getaway a ...
From $445 per night (USD)VRBO
- From $636 per night (USD)
Expedia
Updated Pool Unit at Beachfront Coconuts Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Poolside! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $636 per night (USD)Expedia
- From $725 per night (USD)
VRBO
EV Charger, Portside Paradise by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $725 per night (USD)VRBO
- From $1412 per night (USD)
Expedia
Luxury Home with Pool and Spa! 4 Minutes to the Beach! - Feelin' Beachy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Feelin' Beachy by AMI Locals Holmes Beach Luxury Beach Retreat with Pool VRC20-000140 Prepare for endless enjoyment a ...
From $1412 per night (USD)Expedia
- From $759 per night (USD)
VRBO
The Beach House - sleeps 6 guests in 3 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Beach House is situated on one of the quietest areas of the beautiful white sandy beach. Why not sit on the veranda ...
From $759 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Captain's Quarters: 1 Block to Beach, Dog Friendly, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Captain's Quarters Spinnakers by Anna Maria Life Vacation Rentals 202 56th St #1, Holmes Beach, FL 34217 What You'll Lo ...
From $273 per night (USD)Expedia
- From $479 per night (USD)
VRBO
Condo steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy the beauty of Anna Maria Island! Less than 50 steps from the white sand beach and minutes (.2 miles) from res ...
From $479 per night (USD)VRBO
- Click For Pricing
Expedia
Coconuts Resort Direct Beachfront Bungalow!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Beachside! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
Click For PricingExpedia
- From $584 per night (USD)
VRBO
Luxurious Beach Haven- 2-min walk to beach access, pool, spa and 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 $584 per night (USD)VRBO
- From $536 per night (USD)
Expedia
Experience Island Life! Great private Pool and Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Life by AMI Locals Home in Holmes Beach VRC#18-000083 Welcome to Island Life, a fully renovated and updated vac ...
From $536 per night (USD)Expedia
- Click For Pricing
VRBO
One block off the beach! Waterslide and Rooftop deck!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Pineapple Paradise by AMI Locals Home in Holmes Beach, Florida VRC19-000039 Come and visit Pineapple Paradise! This ...
Click For PricingVRBO
- From $756 per night (USD)
Expedia
Perfect Family Vacation Home with Putting Green, Waterslide - Island Pearl Oasis
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Island Pearl Oasis by AMI Locals Home in Holmes Beach, Florida VRC19-000119 Escape the everyday grind and head ...
From $756 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Beach Haven Ranked #204 for businesses in Holmes Beach FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beach Haven #204 at Seaside Beach House is favorite for guests of Holmes Beach and Anna Maria Island. This 1050 sq ft ...
From $313 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Island Serenity: North Beach Village, Dog Friendly, Short Walk to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Serenity by Anna Maria Life Vacation Rentals 6250 Holmes Blvd. #54, Holmes Beach, FL 34217 What You'll Love Abou ...
From $328 per night (USD)Expedia
- From $702 per night (USD)
VRBO
Beautiful Beach House with Pool Steps to Beach - Harbor Haven
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Harbor Haven by AMI Locals 210 N Harbor Dr Holmes Beach, Florida VRC19-000118 Welcome to Harbor Haven! Stay, relax, ...
From $702 per night (USD)VRBO
- From $467 per night (USD)
Expedia
GULF BEACH Directly in Front w/ Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Perfectly situated on the Gulf of Mexico in the center of Anna Maria Island, ...
From $467 per night (USD)Expedia
- From $369 per night (USD)
VRBO
Beachside Bliss! Pool, Trolley & King Bed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Villa #6 Starfish at Island West Resort by AMI Locals Holmes Beach Villa with Shared Pool Dive into resort-style liv ...
From $369 per night (USD)VRBO
- From $452 per night (USD)
Expedia
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical landscaped sett ...
From $452 per night (USD)Expedia
- From $452 per night (USD)
VRBO
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical landscaped sett ...
From $452 per night (USD)VRBO
- From $371 per night (USD)
Expedia
Cozy AMI Villa! Pool, BBQ & Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Villa #3 Seahorse at Island West Resort by AMI Locals Holmes Beach Villa with Shared Pool Welcome to Villa #3 Seahors ...
From $371 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Beautifully updated home with private pool, close to beach, 2 bedrooms!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sea Grape Escape by AMI Locals Home in Holmes Beach, FL Features: • Pool • Backyard Patio with TV • Beach chairs for g ...
From $325 per night (USD)VRBO
- From $753 per night (USD)
Expedia
Amazing waterfront home with pool and spa, close to beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Paradise by AMI Locals Home in Holmes Beach, Florida VRC18-000090 Welcome to Bayfront Paradise, a truly s ...
From $753 per night (USD)Expedia
- From $273 per night (USD)
VRBO
A lovely 2 bed and 2 bath property just moments from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Seabreeze Cottage is situated on a quiet road with access to the beach, via a leafy lane, just 200 feet away. The prope ...
From $273 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Perfectly Located Near the Beach, Dining, and Shopping!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Saltwater Palms by AMI Locals Holmes Beach Beach Townhome with Pool & Outdoor Entertaining VRC21-000078 Welcome to Sa ...
From $292 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Villa #4 Sand Dollar! Pool, Porch & King Bed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Villa #4 Sand Dollar by AMI Locals Charming Villa Just Steps from the Beach Welcome to Villa 4 Sand Dollar, a cozy o ...
From $371 per night (USD)VRBO
- From $555 per night (USD)
Expedia
September Golf Cart Special
- 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 $555 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Peaceful Poolside Escape Near Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Blue Oasis East by AMI Locals Peaceful Poolside Escape Near Holmes Beach 401 72nd St A | Holmes Beach, Florida VRC21 ...
From $416 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Blue Oasis West! Family-Friendly Duplex Near Shops and Dining
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Blue Oasis West by AMI Locals Home in Holmes Beach VRC21-000103 Welcome to Blue Oasis West, a ground-level home just ...
From $350 per night (USD)Expedia
- From $348 per night (USD)
VRBO
Castnetter Beach Resort 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $348 per night (USD)VRBO
- From $249 per night (USD)
Expedia
DIRECT GULFRONT CONDO - 2BR/2BA Condo with pool and tennis - By Island Real Esta
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“Water’s Edge 204S” is part of the beach side Water’s Edge Condominiums. These condos are perfectly placed, as you’ll se ...
From $249 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Spacious Condo on the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly remodeled condo with a view of the gulf from your relaxing balcony. Large heated pool and hot tub amid lush landsc ...
From $306 per night (USD)VRBO
- Click For Pricing
Expedia
Resort Sixty-Six - Anna Maria Island Quiet Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingExpedia
- From $436 per night (USD)
VRBO
Sun and Surf Direct Gulf Front Condo on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful ...
From $436 per night (USD)VRBO
- From $515 per night (USD)
Expedia
Elevated 3BR/3BA Home - Private Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Updated - New bathrooms and updates completed in February of 2023!! “Forget Me Knot” is a gem among island homes. ...
From $515 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Appletini- Dog Friendly Private Pool Home IN Heart of Anna Maria By Island Real
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tiki waterfall heated pool with comfortable pool side furniture will melt your worries away. This ground level property ...
From $308 per night (USD)VRBO
- From $435 per night (USD)
Expedia
Luxury villa at Islands West Resort, near beach, with pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Villa #7 AMI Lime Fish by AMI Locals Luxury Villa Just Steps from the Gulf Welcome to Villa #7 AMI Lime Fish, a beau ...
From $435 per night (USD)Expedia
- From $648 per night (USD)
VRBO
Private Pool! Ping-Pong, Pool Table, Putt-Putt!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stormalong Bay by Stormalong Bay by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Welcome to Stormal ...
From $648 per night (USD)VRBO
- From $392 per night (USD)
Expedia
Anna Maria Island Townhouse - Simply Beautiful! Your Perfect Vacation Location!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This townhouse is beautifully decorated and completely modernized with everything you need for the perfect vacation in p ...
From $392 per night (USD)Expedia
- From $1014 per night (USD)
VRBO
Ultimate Family Retreat with Pool, Waterslide and Rooftop Deck
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 16
Beach Haven by AMI Locals Ultimate Family Retreat with Pool, Waterslide and Rooftop Deck 5501 Holmes Blvd Holmes Beach ...
From $1014 per night (USD)VRBO
- From $496 per night (USD)
Expedia
SeaStarVilla by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Star Villa! This well constructed 2-bedroom, 3-bathroom Island home with a bonus room is ready to host gu ...
From $496 per night (USD)Expedia
- From $268 per night (USD)
VRBO
Shell Game: Playa Encantada - Beachfront Community Steps to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shell Game has recently been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious ...
From $268 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Cozy Cabana East – AMI w/ Heated Pool, Pets & Walk To The Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Cozy Cabana East! On Anna Maria Island (Holmes Beach, Florida) Managed by Once Upon A Beach Vacation Rentals, ...
From $381 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Beachfront Condo with Stunning Gulf Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Paradise #4 by AMI Locals Condo in Holmes Beach, Florida VRC21-000114 Welcome to Island Paradise #4, a two-bed ...
From $468 per night (USD)VRBO
- From $534 per night (USD)
Expedia
Island Paradise 6! Beachfront Condo with Gulf Views, Pool and Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Paradise #6 by AMI Locals Condo in Holmes Beach, Florida Discover the ultimate beachfront escape at Island Pa ...
From $534 per night (USD)Expedia
- From $781 per night (USD)
VRBO
Tropical Backyard Escape with Pool, Hot Tub, and Waterslide
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Conch House by AMI Locals 307 66th St, Unit B | Holmes Beach, Florida VRC18-000085 Tropical Backyard Escape with Po ...
From $781 per night (USD)VRBO
- From $1113 per night (USD)
Expedia
Beachfront Bliss! Pool, Spa & Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beachfront Bungalow by AMI Locals Holmes Beach Gulf-Front Cottage with Private Pool and Spa VRC19-000270 Welcome to ...
From $1113 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Beach Condo with Pool Near Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Poolside #104 by AMI Locals 100 73rd St, Unit #104, Holmes Beach, FL 34217 VRC16-000664 Welcome to Coconuts ...
From $371 per night (USD)VRBO
- From $334 per night (USD)
VRBO
Private Pool/Spa - A Wave From It All by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Name - A Wave From It All, formerly known as Island Dream, is a recently updated custom home nestled in the quiet re ...
From $334 per night (USD)VRBO
- From $555 per night (USD)
VRBO
Sul Mare at Vista Grande on Anna Maria Island - By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
By far the BEST direct view of the Gulf you will find on Anna Maria Island. Exclusive SUL MARE with floor to ceiling win ...
From $555 per night (USD)VRBO
- From $253 per night (USD)
Expedia
Anna Maria Island condo with heated pool, short walk from the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sea Pirate 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $253 per night (USD)Expedia
- From $153 per night (USD)
VRBO
Sweet duplex with WiFi, central AC, & gas grill - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Coastal Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $153 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Lazy Lizard! A Newly Renovated Island Cottage, Close to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Photos Updated January 2025! LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the night ...
From $214 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Pink Flamingo in Palm Isle Village - 2BR Condo with Pool - By Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the best Anna Maria Island has to offer when you stay in this comfortable condo steps from an amazing white san ...
From $264 per night (USD)VRBO
- From $384 per night (USD)
Expedia
Colorful Beach Cottage w/ Heated Pool + Walk to Sand
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Peacock Crossing by AMI Locals Charming Island Cottage with Heated Pool and Beach Access 205 Peacock Ln, Unit B | Hol ...
From $384 per night (USD)Expedia
- From $797 per night (USD)
VRBO
4 Bedroom Townhouse - Your private Holmes Beach vacation home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the spacious Unit 12, a four-bedroom, three-bathroom townhouse attractively adorned with white walls, cool pa ...
From $797 per night (USD)VRBO
- From $340 per night (USD)
Expedia
AMI Moana Villa 3-minute walk to the beach plus community heated pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Find everything you need for a fun and memorable beach getaway at this three-bedroom Holmes Beach rental! You'll have a ...
From $340 per night (USD)Expedia
- From $963 per night (USD)
VRBO
Summer House-Rooftop, short walk to the beach, private pool/spa and water slide
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 20
At A Glance Short walk to the beach Rooftop deck with Gulf and Bay views Private heated pool with spa, water slide, and ...
From $963 per night (USD)VRBO
- From $1380 per night (USD)
Expedia
Summer Paradise-Rooftop deck and private heated pool/spa
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
At A Glance Two houses down from beach access Rooftop deck with Gulf and Bay views Private heated pool with spa, water ...
From $1380 per night (USD)Expedia
- From $1373 per night (USD)
VRBO
Malibu Beach! 8BR Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 16
Malibu Beach by AMI Locals Home in Holmes Beach, Florida VRC18-000067 Get ready for the ultimate beach vacation at Ma ...
From $1373 per night (USD)VRBO
- From $337 per night (USD)
Expedia
Beautiful Cottage with Private Pool, Great Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Cottage #1 by AMI Locals Condo in Holmes Beach, FL VRC18-000069 Highlights • 1-minute walk from the Beach • Priv ...
From $337 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Ground-floor home with fast WiFi, shared pool, & central AC - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Villas, Condo 1A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $216 per night (USD)VRBO
- From $1205 per night (USD)
Expedia
AMI Escape! 6 King Suites, Bunk Rooms and Game Zone Near Holmes Beach
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Surf View by Anna Maria Island Locals Home in Holmes Beach, FL Highlights • Pool with sundeck, spa, swim-up Tiki table ...
From $1205 per night (USD)Expedia
- From $374 per night (USD)
VRBO
Home 5 Mins to Beach with Private Pool & Pool Table - Three Little Birds Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Three Little Birds Cottage by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Welcome to Three Littl ...
From $374 per night (USD)VRBO
- From $522 per night (USD)
Expedia
Beautiful Beach Home Right Near the Water with Private Pool, AC, & Fast WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Joy Abounds Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $522 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Charming Ground Floor Condo with Shared Pool, High-Speed WiFi, and Central AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Villa 1B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $299 per night (USD)VRBO
- From $962 per night (USD)
Expedia
Large Home Directly on the Beach - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Family friendly with fantastic views and directly on the Gulf of Mexico sound like your idea of a perfect vacation renta ...
From $962 per night (USD)Expedia
- From $971 per night (USD)
VRBO
Luxury Island Escape with Pool, Swim-Up Tiki Bar, Game Room and Rooftop Deck
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 16
Tropical Oasis by Anna Maria Island Accommodations Luxury Island Escape with Pool, Swim-Up Tiki Bar, Game Room and Roo ...
From $971 per night (USD)VRBO
- From $716 per night (USD)
Expedia
Mainsail Beach Inn 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 ...
From $716 per night (USD)Expedia
- From $670 per night (USD)
VRBO
Coastal Sunrise- Luxury 3 bedroom gulf front condo with stunning views with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Luxury Direct Gulf Front Condo Very large unit- 2100 sq ft-Top Floor, Corner Unit Panoramic Gulf views-private stairs fr ...
From $670 per night (USD)VRBO
- From $939 per night (USD)
Expedia
Coastal Bliss- 2-Minute Walk (500 Feet) to the beach with private pool and spa
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
At A Glance 2-Minute Walk (500 Feet) to the Beach! Private Pool and Outdoor Spa, Heated Seasonally Outdoor Bar and Pool ...
From $939 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Cottage with Private Pool! Steps to Beach! - Coconut Cottage 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Cottage #4 by Anna Maria Vacations 108 39th Street, Unit #4, Holmes Beach, Florida VRC 18-000072 Welcome to Co ...
From $294 per night (USD)VRBO
- From $259 per night (USD)
Expedia
Steps to Beach - The Cozzi Cottage by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Brimming with historic character, this charming ground level 1 bedroom/1 bath cottage has a bright modern, organic feel– ...
From $259 per night (USD)Expedia
- From $535 per night (USD)
VRBO
Twin Palms: Big House Close to Beach, Heated Lagoon Pool, Infant/Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Stay at the home of a NY Times best-selling food writer and her architectural designer/tech husband! Pet friendly, lots ...
From $535 per night (USD)VRBO
- From $252 per night (USD)
Expedia
Steps from the Beach 2BR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Coconut AMI unit 1, located at 4104 4th Avenue in Holmes Beach, on Anna Maria Island, a delightful island locale di ...
From $252 per night (USD)Expedia
- From $290 per night (USD)
VRBO
Great location near Manatee Beach 1BR
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great work or study from "home" while on vacation. This unit has large office space in addition to the living area and i ...
From $290 per night (USD)VRBO
- From $223 per night (USD)
Expedia
2BR Steps from Manatee Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Coconut AMI unit 2 is located at 4104 4th Avenue in Holmes Beach, on Anna Maria Island, a delightful island locale ...
From $223 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Terrace Condo 1 Pool Condo Relaxing Tropical Pool Deck Close To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC 19-00237 The Terrace Condominium #1, located at 3100 Gulf Drive in Holmes Beach is a beautifully and comfortably fu ...
From $233 per night (USD)VRBO
- From $733 per night (USD)
Expedia
Stylish Coastal Escape with Pool Near Beach and Trolley
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Take Me Away by AMI Locals Stylish Coastal Escape with Pool Near Beach and Trolley 214 69th Street Holmes Beach, FL ...
From $733 per night (USD)Expedia
- From $243 per night (USD)
VRBO
⚓3/2.5 Private Canal Front Pool Home on AMI⚓Close To Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location, Location (see map): There are seven miles of pristine, quartz sand beaches shimmering along our island and you ...
From $243 per night (USD)VRBO
- From $345 per night (USD)
Expedia
Sunrise Bay Unit B! Heated pool! Walk to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a spacious completely updated ground floor 2/2. Unit B is part of a 2 unit duplex with a private porch and grill ...
From $345 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Beachside getaway! Adorable home with pool spa access! 5 min walk to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is unit A in a 2 unit duplex. The place has been completely upgraded from top to bottom with brand new everything. ...
From $276 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Walk to Beach: Home w/ Porch on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Map out your coastal Florida escape to this warm and welcoming 2-bedroom, 2-bathroom vacation rental located on Anna Mar ...
From $209 per night (USD)Expedia
- From $413 per night (USD)
VRBO
Ebb Tide by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3-bedroom, 3-bath pool home is well ...
From $413 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Perfect Island Getaway for Families! Private pool, Close to the Beach! - Coconut
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Cottage #3 by AMI Locals 108 39th Street, Unit 3, Holmes Beach, Florida VRC18-000071 Welcome to Coconut Cotta ...
From $313 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Casa Sierra 203A - 2BR Condo with Pool By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This small quiet complex is just a two minute walk to the beautiful white sand beach. A ground level unit, find an outdo ...
From $336 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Casa Sierra 205B - 2BR Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
When you visit the quiet four unit Casa Sierra complex you’ll enjoy great amenities like the shared heated pool with per ...
From $303 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Casa Sierra 205A - 2BR Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a two minute walk to the beach! Casa Sierra 205 A 36th Street in Holmes Beach. Sleeps (6), (2) Bedroom (2) Bathroom ...
From $325 per night (USD)VRBO
- From $636 per night (USD)
Expedia
Private Heated Pool Home in Holmes Beach - Fernweh - By Island Real Estate Vaca
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Fernweh! (Means to crave for travel; being homesick for a place you've never been) New Luxury Home located at ...
From $636 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Beautiful 3BR /2BA, Family Friendly Home w/Private pool/patio area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom 2 bathroom vacation home on beautiful Anna Maria Island, Just two short blocks from the most breathtaking whit ...
From $404 per night (USD)VRBO
- From $368 per night (USD)
Expedia
Beautiful 3Bed/3 Bath, Heated Pool, WiFi & Trolley, Stroll to Pristine Beach,...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Forget your cares at this thoughtfully renovated 3 bedroom, 3 bath, pool hom ...
From $368 per night (USD)Expedia
- From $208 per night (USD)
VRBO
Fountainhead Condo 3 2/2 Condo Steps To white Sugar Sand Beach, Large Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC21-000076 Fountainhead Condo #3, located at 3402 6th Avenue in Holmes Beach is just a few steps from the beautiful b ...
From $208 per night (USD)VRBO
- From $781 per night (USD)
Expedia
Tiki a Gulf-Front Escape with Unmatched Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000568 Tiki | Gulf-Front Escape with Unmatched Views Your Private Slice of Paradise Awaits! Perched directly on ...
From $781 per night (USD)Expedia
- From $319 per night (USD)
VRBO
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a gr ...
From $319 per night (USD)VRBO
- From $391 per night (USD)
Expedia
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Breeze (Units A and B) is your new paradise. Each 2 bedroom 2 bath side of this adorable duplex features everythin ...
From $391 per night (USD)Expedia
- From $221 per night (USD)
VRBO
A Wright Place 2/2 Private Pool Duplex Short Block To Beautiful Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000511 A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside ...
From $221 per night (USD)VRBO
- From $817 per night (USD)
Expedia
Breakers 1 | A Classic Old Florida Beach Cottage – Fully Restored
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Some homes are more than just a place to stay—they hold a story. Breakers 1 is one of the few remaining Old Florida coas ...
From $817 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Island Cottage with open living area, pool, ground floor very close to beach located in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half d ...
From $426 per night (USD)VRBO
- From $486 per night (USD)
Expedia
3 bedroom, luxury beach house on Anna Maria Island, private pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Villa welcomes you to sunny AMI! Palm Villa is a very comfortable, casual, but well-appointed Florida island getawa ...
From $486 per night (USD)Expedia
- From $349 per night (USD)
VRBO
Holmes Beach Cottage Steps to the Beach with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack i ...
From $349 per night (USD)VRBO
- From $300 per night (USD)
Expedia
SS Salamander South | Steps to the Beach + Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
VRC16-000500 Your Holmes Beach Escape Awaits Tucked just one block from the pristine Gulf beaches, SS Salamander South ...
From $300 per night (USD)Expedia