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 $346 per night (USD)
VRBO
NEW Beachfront..Island Beach Club - Gorgeous First Floor 2 Bed, 2 bath with Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy this newly Updated, Spacious First Floor Condo located on the beach. You have private beach access and a beautifu ...
From $346 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Winter Escape to Sunny 🏝️ 5 min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this stunning beach house, just steps away from the sugary sand beaches of Anna Maria Island! This gem is not ...
From $317 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Cheeky Chateau: Cozy Retreat with Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your island getaway at the Cheeky Chateau in Holmes Beach! This cozy retreat on Anna Maria Island is your tic ...
From $482 per night (USD)
VRBO
From $141 per night (USD)
Expedia
Wonderful studio near the beautiful beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shortboard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $141 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Cottage near the Beach with Paddleboards and More! - A Lil' Nauti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Lil' Nauti by Anna Maria Vacation Home in Holmes Beach, FL 34217 Welcome to A Lil' Nauti, a ground-level home featuri ...
From $168 per night (USD)
VRBO
From $615 per night (USD)
Expedia
Octopus Cottage: 1.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Octopus Cottage by Anna Maria Life Vacation Rentals 209 69th St, Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $615 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Sunday Funday managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sunday Funday 517 42nd St Holmes Beach, FL 34217 2 Blocks to Beach Sunday Funday is fun and beachy 3 bedroom home locate ...
From $407 per night (USD)
VRBO
Click For Pricing
Expedia
The Wave by Beach Boutique Rentals
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Escape to paradise and indulge in opulence like never before at our brand new, funky and contemporary 4-bedroom, 4-bathr ...
Click For Pricing
Expedia
$7310 Holmes - Duplex 1 Bedroom \/ 1 Bath , maximum occupancy of 4 people.$
From $260 per night (USD)
VRBO
7310 Holmes - Duplex 1 Bedroom \/ 1 Bath , maximum occupancy of 4 people.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
7310 Holmes Boulevard, Unit B - Anna Maria Island - Duplex - 1 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC16-00 ...
From $260 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Enjoy Salty Soul: Canal Front Family Retreat with Kayaks on Anna Maria Island!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Salty Soul by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to Salty Soul, the ideal family g ...
From $266 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Rest Assured - Ground Level Pool Home - By Island Real Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your coastal retreat on Holmes Beach, where sun-soaked days and balmy nights await! This charming three-bedro ...
From $543 per night (USD)
VRBO
From $1422 per night (USD)
Expedia
Anna Maria Wave: Stunning Beachfront Home with Pool & Poker Room
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E Holmes Beach, FL 34217 Escape to paradise in this stu ...
From $1422 per night (USD)
Expedia
$Cozy Cabana West - Updated Adorable Bungalow w\/Heated Private Pool, Walk to Beach$
From $531 per night (USD)
VRBO
Cozy Cabana West - Updated Adorable Bungalow w\/Heated Private Pool, Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Cozy Cabana West! On Anna Maria Island (Holmes Beach, Florida) After sustaining hurricane damage, this charm ...
From $531 per night (USD)
VRBO
From $661 per night (USD)
Expedia
La Isla Bonita by Coastal Chic Vacations
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to La Isla Bonita; New home under our management! - Steps to Anna Maria Island's powdery-white sandy beaches - ...
From $661 per night (USD)
Expedia
From $715 per night (USD)
VRBO
Location! Heated Pool, Elevator, Toys, Walk to Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Under new management May 2025! Welcome to Shore to Please (5 Star), an exquisite vacation home that perfectly blends lu ...
From $715 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Crab Shack by A Shore Thing Vacations
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to your dream Anna Maria Island getaway! This charming 2-bedroom, 3-bathroom beach house is just 2 blocks from t ...
From $610 per night (USD)
Expedia
From $505 per night (USD)
VRBO
3000 sq ft, 8 person , 3 bdrm home with large heated pool ,outdoor space & more
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly remodeled! New to renters!Experience Anna Maria Island like a local in this very large charming house. Just a sho ...
From $505 per night (USD)
VRBO
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Expedia
Playa Palma Private Pool Home 4 Minute Walk to Holmes Beach on AMI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover this lovely 3-bedroom gem in Holmes Beach. Relax pool side in lush landscaping at our home just 1.5 blocks fro ...
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Expedia
From $340 per night (USD)
VRBO
PETS STAY FREE!! Heated Pool 1.5 Blocks from Beach Good for Couples or Families
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom house in Holmes Beach. With a king bed, queen bed, and twin bed, this delightful pr ...
From $340 per night (USD)
VRBO
From $837 per night (USD)
Expedia
Lux 3B3Ba StepsToTheBeach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Ah, the smell of salt and sand. There's no elixir on this blessed earth like it. Our luxury Anna Maria Island Townhome ...
From $837 per night (USD)
Expedia
From $1129 per night (USD)
VRBO
Sea Haven:Family home steps to beach, pool, hot tub, Foosball, putting green!
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
Photos Updated March 2025! Welcome to Sea Haven, a spacious and inviting 5-bedroom, 4.5-bathroom home just three houses ...
From $1129 per night (USD)
VRBO
From $1212 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 ...
From $1212 per night (USD)
Expedia
From $352 per night (USD)
VRBO
NEW Coastal Luxury, so close to the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Modern & comfortable 2-bedroom, 2-bathroom stay is a short couple minute walk to the white sand beach of Anna Maria Isla ...
From $352 per night (USD)
VRBO
From $1074 per night (USD)
Expedia
Coconuts Beachfront #106: Ultimate Island Getaway with Beach Access and Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconuts Beachfront #106 by AMI Locals 100 73rd St Unit 106 - Holmes Beach, FL 34217 Welcome to Coconuts Beachfront #10 ...
From $1074 per night (USD)
Expedia
From $553 per night (USD)
VRBO
TROPICAL TREEHOUSE - 6250
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to “Tropical Treehouse” on Anna Maria Island… a cozy resort style 2 story townhome surrounded by lush, tropical ...
From $553 per night (USD)
VRBO
From $787 per night (USD)
Expedia
One Of The Most Unique Homes in Anna Maria Island
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property Summary Property Ref: AMI_5000R | Happy Place | 5601 Flotilla Dr, Holmes Beach, Fl *Minimum of 30 Nights Requi ...
From $787 per night (USD)
Expedia
From $713 per night (USD)
VRBO
Large pool home just steps from the Gulf, fully renovated, family friendly, WIFI
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
King Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $713 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Full complex perfect for families with private pool and just steps to the Gulf
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Gertie's Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $736 per night (USD)
Expedia
$Island Vacay -1 Block Walk\/quiet street to beach$
From $261 per night (USD)
VRBO
Island Vacay -1 Block Walk\/quiet street to beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy ...
From $261 per night (USD)
VRBO
$1 Block WALK on QUIET street to beach\/food\/fun$
From $292 per night (USD)
Expedia
1 Block WALK on QUIET street to beach\/food\/fun
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Dreaming of an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share ...
From $292 per night (USD)
Expedia
$1 BLOCK WALK-QUIET St. to beach\/food\/fun\/sun\/shops$
From $459 per night (USD)
VRBO
1 BLOCK WALK-QUIET St. to beach\/food\/fun\/sun\/shops
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only shar ...
From $459 per night (USD)
VRBO
From $393 per night (USD)
Expedia
Oceanside Retreat-Rest & Recover-Hot Tub-Hammock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Whether escaping the cold winter days, or wanting to unwind from all the stress, Solace West is the perfect place for yo ...
From $393 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Tranquility Meets Style-Walk to beach-prvt pool.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Winter has hit hard and you are ready to escape the frigid temperatures and feel the sand between your toes. Anna Maria ...
From $372 per night (USD)
VRBO
$Hello, Sunshine! 🌞 Cozy Island Stay W\/ Deck, Bikes & More!$
From $335 per night (USD)
Expedia
Hello, Sunshine! 🌞 Cozy Island Stay W\/ Deck, Bikes & More!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
- Spacious Outside Deck for Entertainment - Stocked Closet with Bikes and Beach Equipment - Steps Away From Sugar Sand B ...
From $335 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Ideal Island-style townhome only 460 steps to WOW of a beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience the ultimate island getaway in a charming rental property that offers everything you need for a relaxing beac ...
From $435 per night (USD)
VRBO
$Tipsy Turtle! Waterfront W\/ boat lift & walk to beach access$
From $759 per night (USD)
Expedia
Tipsy Turtle! Waterfront W\/ boat lift & walk to beach access
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This waterfront home has 80 feet of canal frontage including dock and boat lift for up to 10,000 lbs. Perfect for easy a ...
From $759 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Sea Glass: 3-Bedroom Retreat Steps from the Beach, Private Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sea Glass by Anna Maria Island Accommodations 208 66th St Unit A Holmes Beach, FL 34217 Welcome to Sea Glass! Discover ...
From $611 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Golf Cart - Beachy Keen by SeaBreeze Vacation
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS CREATED AFTER 12/18/24! All Drivers must be over the age of 21. Driv ...
From $864 per night (USD)
Expedia
From $395 per night (USD)
VRBO
The Magic Dolphin B in Holmes Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use th ...
From $395 per night (USD)
VRBO
From $407 per night (USD)
Expedia
The Magic Dolphin A in Holmes Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use th ...
From $407 per night (USD)
Expedia
From $780 per night (USD)
VRBO
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 $780 per night (USD)
VRBO
From $1843 per night (USD)
Expedia
Brand New Luxury Home! ~200 Steps to Beach, Heated Pool, Hot Tub, Fireplace
Bedrooms:
5
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 $1843 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Anna Maria Island Family-Friendly Waterfront Paradise with Pool!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Coral Castle by AMI Locals Home in Holmes Beach, Florida Welcome to Coral Castle, your enchanting waterfront escape ...
From $736 per night (USD)
VRBO
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Expedia
Luxury Pool Home: 5 Minutes to the Beach on Anna Maria Island
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Summer Retreat by AMI Locals Home in Holmes Beach, FL 34217 Experience the Summer Retreat! This luxurious three-story ...
Click For Pricing
Expedia
From $355 per night (USD)
VRBO
3 Bed and 3 Bath Condo: 6 min stroll to the beach with a rare view of the...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 Bed and 3 Bath Condo: 6 min stroll to the beach with a rare view of the mangroves. VRC21-004876 ...
From $355 per night (USD)
VRBO
From $826 per night (USD)
Expedia
Experience Luxury at Marmalade Sky - Pool, Rooftop Deck, 6 Mins to Beach!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Marmalade Sky by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to Marmalade Sky, a luxurious ...
From $826 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Hav'Anna Daydreamin': Pool, 1 Block to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Hav'Anna Daydreamin' by Anna Maria Life Vacation Rentals 204 Archer Way, Anna Maria, FL 34216 What You'll Love About Th ...
From $444 per night (USD)
VRBO
From $598 per night (USD)
Expedia
Luxury Retreat for Sophisticated Travelers
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to LaPlage Unit #3, a luxurious Gulf-front condo that offers sophisticated travelers a serene retreat on the pris ...
From $598 per night (USD)
Expedia
From $293 per night (USD)
VRBO
AMI 2 bedroom, Updated condo with pool in fantastic location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sunny Daze! This newly remodeled two bedroom two bath beautiful condo is located in the heart of Holmes Bea ...
From $293 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Cozy Vacation Rental in a great location
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Property Summary Property Ref: AMI_5001R | Happy Place | 5601 Flotilla Dr, Holmes Beach, Fl Highlights 7-minute walk t ...
From $151 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Private Duplex. Minutes to the Beach, Shopping, Dining - Key Lime Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key Lime Cottage by Anna Maria Vacations Home in Holmes Beach, Fl. 34217 VRC16-000746 Welcome to Key Lime Cottage! T ...
From $405 per night (USD)
VRBO
From $684 per night (USD)
Expedia
La Casa Costiera 12- 3 bedroom beachfront condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
La Casa Costiera 12 7324 Gulf Drive Unit 12, Holmes Beach, FL 34317 What you will love about this property: • Luxury con ...
From $684 per night (USD)
Expedia
From $573 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 $573 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Quiet Oceanfront Resort located on Anna Maria Island May 3- May 10, 2025
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Resort Sixty Six is a small 2 story resort located within steps of the ocean. 2nd floor studio room features newly remo ...
From $186 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Luxury Beach Escape - 5 Min Walk to Pristine Shores of Anna Maria Island - GREAT
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Summary: This beautifully designed 3-bedroom, 2-bathroom home is a true island oasis, just a 5-minute walk to the beach ...
From $320 per night (USD)
VRBO
$Low Rates for longer stays! Perfect Location! \nSteps to Beach!\/Heated pool!$
From $262 per night (USD)
Expedia
Low Rates for longer stays! Perfect Location! \nSteps 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 $262 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Beach Escape, Heated Private Pool, 11-Foot Ceilings, 75-Inch TV, Modern Luxury
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Island Breeze your dream beach getaway on Anna Maria Island. Step into a bright, 3-bedroom, 2-bath home with ...
From $457 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Waterfront Condo on Anna Maria Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to paradise! The Westbay Point and Moorings complex is a private and spacious waterfront community offering an ...
From $444 per night (USD)
Expedia
$Anna Maria Island Gulf View, Steps to Beach, 2br\/2ba$
From $237 per night (USD)
VRBO
Anna Maria Island Gulf View, Steps to Beach, 2br\/2ba
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully furnished 2br/2ba gulf view condo steps to the beach, in Holmes Beach on Anna Maria Island. Walk to dining, ...
From $237 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Cool Breeze by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for the ultimate beachfront vacation experience? Look no further than Cool Breeze, a stunningly remodeled 2 bedr ...
From $519 per night (USD)
Expedia
$Martinique 308 South - Condo 2 Bedroom \/ 2 Bath gulf view , maximum...$
From $263 per night (USD)
VRBO
Martinique 308 South - Condo 2 Bedroom \/ 2 Bath gulf view , maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Martinique 308 South - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC#20-000122 ...
From $263 per night (USD)
VRBO
Click For Pricing
Expedia
A week on the beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy resort with a beautiful beachfront on the north side of Ana Maria Island with shopping and dining nearby. One bedro ...
Click For Pricing
Expedia
From $469 per night (USD)
VRBO
Beautiful House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to the Beach with Heated Pool / 3 bedroom plus game area / den Located on the North End of Holmes Beach near Cros ...
From $469 per night (USD)
VRBO
From $386 per night (USD)
Expedia
A Reel Beauty: 2 Blocks to Beach! Pool, Spa, Putting Green, by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
4803 2nd Ave, Holmes Beach, FL 34217 What You'll Love About this Home: Location! 2 Blocks to the Beach! 3 Bedrooms / 3 ...
From $386 per night (USD)
Expedia
From $525 per night (USD)
VRBO
La Coconut: 1 Block to Beach! Dog Friendly! Ping Pong & Foosball, Heated Pool by Anna Maria Life
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
La Coconut by Anna Maria Life Vacation Rentals 3610 Gulf Drive, Holmes Beach, FL 34217 What You'll Love About this Home ...
From $525 per night (USD)
VRBO
From $817 per night (USD)
Expedia
5 bedroom canal home on AMI, heated pool, pet friendly!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Harborside, a gorgeous canal front home located in Holmes Beach. This is where you’ll want to be for your nex ...
From $817 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Heron Heaven - 3 bedroom private pool home across street from beach - By Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Two-story beach house, just a short walk away from Gulf sands, with a rooftop deck and luxurious private pool. A 3 bed t ...
From $533 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Dilly Dally by the Seas: 1 Block to Beach, Rooftop Deck, Pool & Spa by Anna Maria Life
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Dilly Dally by Anna Maria Life Vacation Rentals 7005 Gulf Dr, Holmes Beach, FL 34217 What You'll Love About This Home: ...
From $734 per night (USD)
Expedia
$North Beach Village 6301 - 3BR\/2BA Townhome - Anna Maria Island - By Island Real$
Click For Pricing
VRBO
North Beach Village 6301 - 3BR\/2BA Townhome - Anna Maria Island - By Island Real
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A charming island condo, located in the peaceful North Beach Village community, only a block away from the Gulf of Mexic ...
Click For Pricing
VRBO
$At Ease West: A tropical rental 1\/2 block from the beach$
From $232 per night (USD)
Expedia
At Ease West: A tropical rental 1\/2 block from the beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location, location, location! What more could you want from a beach house than a gorgeous pool and a half-block stroll t ...
From $232 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Anna Maria Island Fully Remodeled Vacation Rental
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen ...
From $182 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Coco Cay - Beautiful totally remodeled 4 bedroom with private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Coco Cay 408 71st Street, Holmes Beach, Fl 34217 What you will love about this property: • Recently renovated • Screened ...
From $605 per night (USD)
Expedia
From $1239 per night (USD)
VRBO
Grains of Sand by Beach Boutique Rentals
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Grains of Sand is a stunning custom home located directly across from the beautiful Gulf of Mexico. This home boasts alm ...
From $1239 per night (USD)
VRBO
From $1617 per night (USD)
Expedia
Family vacation home one block to beach with pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Walking distance to many shops, eateries, free trolley, and beach. Enjoy the overstocked beach items the home has to off ...
From $1617 per night (USD)
Expedia
From $993 per night (USD)
VRBO
Gorgeous 4 bed 4 bath, units C and D
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Duplex C and D are each 2/2 under a shared roof. Units are next to each other and completely updated, tastefully decorat ...
From $993 per night (USD)
VRBO
From $807 per night (USD)
Expedia
Entire home near the beach with pool and spa access! Great for larger families!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This amazing duplex consists of unit B which is a 2/2 and unit A 2/1. Both units are completely updated with access to ...
From $807 per night (USD)
Expedia
From $948 per night (USD)
VRBO
Beachfront on Anna Maria Island!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous ...
From $948 per night (USD)
VRBO
From $711 per night (USD)
Expedia
Miller Time managed by Beach Retreats FL Anna Maria Island
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Luxury 4-Bedroom Island Getaway with Pool, Spa, and Game Room - Just Steps from Holmes Beach! Welcome to your dream vac ...
From $711 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Steps to the Beach, Private Half Duplex, Private Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to the latest addition to our Lizzie Lu's Island Retreat family of vacation rentals! Here at Latitude Cottage yo ...
From $626 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Beautiful Private Half Duplex Steps from the Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to the latest addition to our Lizzie Lu's Island Retreat family of vacation rentals! Here at Longitude Cottage y ...
From $668 per night (USD)
Expedia
From $529 per night (USD)
VRBO
3 bedroom luxury home on AMI, private heated pool, pet friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Do not miss this Gem in the sought after Key Royale neighborhood on Anna Maria Island. The open concept offers luxury li ...
From $529 per night (USD)
VRBO
$Relax by the pool, 4 bd\/3.5ba, pool, beach gear!$
From $639 per night (USD)
Expedia
Relax by the pool, 4 bd\/3.5ba, pool, beach gear!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Inquire for monthly rentals Welcome home to your tranquil retreat, where every corner beckons you to unwind and rejuven ...
From $639 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
Comfortable vacation home directly on the beach and sunsets from the terrace
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
We have found our perfect spot on the beach. After visited the resorts and beaches of Florida for many years we are here ...
From $1045 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Bay Palms,3BR 2B , Private Pool with Spa--Entire Home recently renovated.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our home has 3 bedrooms, master with queen bed and ensuite bathroom, 2nd bedroom has a queen bed, 3rd bedroom has two tw ...
From $436 per night (USD)
Expedia
$Lovely corner home near the beach with private pool\/spa, WiFi & central AC$
From $344 per night (USD)
VRBO
Lovely corner home near the beach with private pool\/spa, WiFi & central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mermaid Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $344 per night (USD)
VRBO
$BEAUTIFUL 3\/2 TOWNHOME w\/ HEATED PRIVATE POOL. STEPS FROM THE GULF BEACHES!!$
From $478 per night (USD)
Expedia
BEAUTIFUL 3\/2 TOWNHOME w\/ HEATED PRIVATE POOL. STEPS FROM THE GULF BEACHES!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! Welcome to your Anna Maria Island vacation! You will enjoy your time at thi ...
From $478 per night (USD)
Expedia
From $317 per night (USD)
VRBO
LaBella Casa: Games, updated beachy chic home moments to the Gulf!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
With a bright green-colored exterior and vibrant greenery surrounding the property, LaBella Casa is hard to miss! And, y ...
From $317 per night (USD)
VRBO
From $617 per night (USD)
Expedia
Beach Escape in Holmes Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house ...
From $617 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Villa Verde-4 bedroom with private pool with restaurants and boutiques nearby
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
311 61st Street is a lovely elevated 4 bedroom and 3.5 bathroom tucked away in the heart of Holmes Beach just a short tw ...
From $530 per night (USD)
VRBO
From $253 per night (USD)
Expedia
SeaDuction of Anna Maria Island - 100% up & running after hurricanes!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, ...
From $253 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Cozy corner beach house with pool- 1 block from beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa de Palmas is a charming 3 bedroom and 3 bath private beach house, located one block from the turquoise waters of th ...
From $486 per night (USD)
VRBO
From $549 per night (USD)
Expedia
Stillpoint: Heated pool, 2-min walk to beach, sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Photos updated March 2025 Welcome to the graceful beauty of Stillpoint, an island retreat for family and friends just s ...
From $549 per night (USD)
Expedia
$Renovated home w\/fenced yard, brand-new pool, spa, foosball - steps to beach$
From $399 per night (USD)
VRBO
Renovated home w\/fenced yard, brand-new pool, spa, foosball - steps to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Salt & Sunny Days Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $399 per night (USD)
VRBO
From $524 per night (USD)
Expedia
TranquiliSea: Pet friendly, long term discount, sleeps 12, resort-style pool!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 5% discount on the nightly rate. (This discount is app ...
From $524 per night (USD)
Expedia
$BEAUTIFUL 2\/2 CONDO. 2 HEATED COMMUNITY POOLS. WALKING DISTANCE TO GULF WATERS.$
From $187 per night (USD)
VRBO
BEAUTIFUL 2\/2 CONDO. 2 HEATED COMMUNITY POOLS. WALKING DISTANCE TO GULF WATERS.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! What a gem of a spot to spend your Anna Maria Island vacation! This lovely t ...
From $187 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Bikinis and Board Shorts A: Private pool, 2-mins to beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bring your bikinis and board shorts to this lovely 2 bedroom, 1 bath villa a short block to the gorgeous white sand beac ...
From $262 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Bikinis and Board Shorts B: Private pool, 2-mins to beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Bring your bikinis and board shorts to this lovely 2 bedroom, 2 bath villa a short block to the gorgeous white sand beac ...
From $282 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Tropical luxury beach home with heated pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Introducing Island Oasis an extravagant three bedroom and three bathroom pool home centrally located on Anna Maria Islan ...
From $525 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Dolphin Resort by Duncan Real Estate
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Dolphin Resort! This beautiful, centrally located 3 bedrooms, 2 1/2 bathrooms house has 1,612 sq ...
From $451 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Make Memories at Coveside Cottage: Your Family-Friendly Pool Home Near the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coveside Cottage by AMI Locals Home in Holmes Beach, Florida Welcome to Coveside Cottage, a serene coastal retreat feat ...
From $362 per night (USD)
Expedia

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