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 $513 per night (USD)
VRBO
Castaway Cottage! Beautiful Pool/Spa, Steps to sand, New Golf Cart.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This property is managed by Beach Life Rentals & Sales on Anna Maria Island. Attention all beach lovers! This charming f ...
From $513 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Cottage near the Beach with Paddleboards and More! - A Lil' Nauti
Bedrooms:
1
Bathrooms:
1
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 $180 per night (USD)
Expedia
From $657 per night (USD)
VRBO
Octopus Cottage: 1.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals
Bedrooms:
4
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 $657 per night (USD)
VRBO
From $360 per night (USD)
Expedia
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 $360 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $137 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 $137 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Island 🏝️ Escape on Private Street – 5 min Walk to Beach & Dining
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)
VRBO
From $448 per night (USD)
Expedia
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 $448 per night (USD)
Expedia
From $314 per night (USD)
VRBO
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 $314 per night (USD)
VRBO
From $163 per night (USD)
VRBO
White Pelican - 1000 Feet to the Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The White Pelican, your charming retreat on Anna Maria Island! Nestled just 1000 feet from the pristine sands ...
From $163 per night (USD)
VRBO
From $639 per night (USD)
VRBO
Rest Assured - Ground Level Pool Home - By Island Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your coastal retreat on Holmes Beach, where sun-soaked days and balmy nights await! This charming three-bedro ...
From $639 per night (USD)
VRBO
From $624 per night (USD)
Expedia
La Casa Costiera 12- 3 bedroom beachfront condo
Bedrooms:
2
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 $624 per night (USD)
Expedia
From $312 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 $312 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Hav'Anna Daydreamin': Pool, 1 Block to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
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 $347 per night (USD)
Expedia
From $504 per night (USD)
VRBO
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 $504 per night (USD)
VRBO
From $253 per night (USD)
Expedia
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 $253 per night (USD)
Expedia
From $148 per night (USD)
VRBO
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 $148 per night (USD)
VRBO
From $400 per night (USD)
Expedia
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 $400 per night (USD)
Expedia
From $731 per night (USD)
VRBO
Anna Maria Island Family-Friendly Waterfront Paradise with Pool!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Coral Castle by AMI Locals Home in Holmes Beach, Florida Welcome to Coral Castle, your enchanting waterfront escape ...
From $731 per night (USD)
VRBO
Click For Pricing
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 $338 per night (USD)
VRBO
Eileen's House- One house from the Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Holmes Beach at this fabulous house. With 2 bedrooms featuring a king bed and a full bed, al ...
From $338 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Experience Luxury at Marmalade Sky - Pool, Rooftop Deck, 6 Mins to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Marmalade Sky by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to Marmalade Sky, a luxurious ...
From $646 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Enjoy Salty Soul: Canal Front Family Retreat with Kayaks on Anna Maria Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Salty Soul by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to Salty Soul, the ideal family g ...
From $202 per night (USD)
VRBO
From $1004 per night (USD)
Expedia
Anna Maria Wave: Stunning Beachfront Home with Pool & Poker Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E Holmes Beach, FL 34217 Escape to paradise in this stu ...
From $1004 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Playa Palma Private Pool Home 4 Minute Walk to Holmes Beach on AMI
Bedrooms:
2
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 from ...
From $600 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Crab Shack by A Shore Thing Vacations
Bedrooms:
2
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 $597 per night (USD)
Expedia
From $415 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 $415 per night (USD)
VRBO
From $340 per night (USD)
Expedia
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)
Expedia
From $621 per night (USD)
VRBO
Lux 3B3Ba Steps to Beach! New May Photos
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 $621 per night (USD)
VRBO
From $807 per night (USD)
Expedia
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 $807 per night (USD)
Expedia
From $1212 per night (USD)
VRBO
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)
VRBO
From $359 per night (USD)
Expedia
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 $359 per night (USD)
Expedia
From $497 per night (USD)
VRBO
Coconuts Beachfront #106: Ultimate Island Getaway with Beach Access and Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #106 by AMI Locals 100 73rd St Unit 106 - Holmes Beach, FL 34217 Welcome to Coconuts Beachfront #10 ...
From $497 per night (USD)
VRBO
From $323 per night (USD)
Expedia
TROPICAL TREEHOUSE - 6250
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to “Tropical Treehouse” on Anna Maria Island… a cozy resort style 2 story townhome surrounded by lush, tropical ...
From $323 per night (USD)
Expedia
From $684 per night (USD)
VRBO
One Of The Most Unique Homes in Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Property Summary Property Ref: AMI_5000R | Happy Place | 5601 Flotilla Dr, Holmes Beach, Fl *Minimum of 30 Nights Requi ...
From $684 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Cozy Cabana West - Updated Adorable Bungalow w/Heated Private Pool, Walk to Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Cozy Cabana West! On Anna Maria Island (Holmes Beach, Florida) After sustaining hurricane damage, this charm ...
From $478 per night (USD)
Expedia
From $656 per night (USD)
VRBO
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 $656 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Location! Heated Pool, Elevator, Toys, Walk to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Shore to Please, an exquisite vacation home that perfectly blends luxury and comfort, offering an elevator fo ...
From $526 per night (USD)
Expedia
From $348 per night (USD)
VRBO
The Magic Dolphin B in Holmes Beach
Bedrooms:
2
Bathrooms:
1
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 $348 per night (USD)
VRBO
From $344 per night (USD)
Expedia
The Magic Dolphin A in Holmes Beach
Bedrooms:
2
Bathrooms:
1
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 $344 per night (USD)
Expedia
From $704 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 $704 per night (USD)
VRBO
From $1477 per night (USD)
Expedia
Brand New Luxury Home! ~200 Steps to Beach, 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 $1477 per night (USD)
Expedia
From $737 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 CREATED AFTER 12/18/24! All Drivers must be over the age of 21. Driv ...
From $737 per night (USD)
VRBO
From $679 per night (USD)
Expedia
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 $679 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Full complex perfect for families with private pool and just steps to the Gulf
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Gertie's Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $670 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Island Vacay -1 Block Walk/quiet street to beach
Bedrooms:
1
Bathrooms:
1
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 $227 per night (USD)
Expedia
From $248 per night (USD)
VRBO
1 Block WALK on QUIET street to beach/food/fun
Bedrooms:
2
Bathrooms:
2
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 $248 per night (USD)
VRBO
From $413 per night (USD)
Expedia
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 $413 per night (USD)
Expedia
From $515 per night (USD)
VRBO
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 $515 per night (USD)
VRBO
From $413 per night (USD)
Expedia
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 $413 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Ideal Island-style townhome only 460 steps to WOW of a beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the ultimate island getaway in a charming rental property that offers everything you need for a relaxing beac ...
From $415 per night (USD)
VRBO
From $590 per night (USD)
Expedia
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 $590 per night (USD)
Expedia
From $896 per night (USD)
VRBO
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 $896 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Honu Hale: Enjoy your tropical getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Honu Hale by Anna Maria Island Accommodations 306 55th St, Holmes Beach, FL 34217 Welcome to Honu Hale, your tropical i ...
From $415 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Beached Inn by Duncan Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vacation like an Islander in our lovely three-bedroom pool home located two blocks from the sugar sand beaches of Anna M ...
From $394 per night (USD)
VRBO
From $452 per night (USD)
Expedia
DIRECT GULF-FRONT 2BR/2BA Condo with 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 $452 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Bayside relaxing five minutes walk to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
<p>Located in Holmes Beach, this welcoming vacation home lets you experience it all. Anna Maria Sound is just steps away ...
From $236 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Walk to Gulf: Luxe Luau-Themed Gem in Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly Remodeled | Family Friendly | Al Fresco Dining | BBQ Ready Enjoy a one-of-a-kind stay in the Sunshine State at th ...
From $414 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Just Listed! 3600 SF Spacious Home, Large Pool & Steps to the Sand
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Be among the first to enjoy this newly available island retreat! With over 3,600 sq ft, this spacious home is perfect fo ...
From $557 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Gulf View Getaway | Sand & Sunset Views Daily!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to Gulf View Getaway, your relaxing island retreat where breathtaking Gulf views and unforgettable beachside mem ...
From $308 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Enjoy the waterslide heated pool home! Perfect for adults & kids of all ages. Owner managed. This exceptional 4 bed, 6 & ...
From $709 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Gulf Breeze in Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to "Gulf Breeze" Your Island Retreat in Holmes BeachLooking for your perfect island escape? "Gulf Breeze" is a ...
From $313 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Sandy Pointe 202 - 2BR Island 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 $189 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 $299 per night (USD)
VRBO
Luxury Beach Home - 5 Min Walk to Pristine Shores of Anna Maria Island - GREAT f
Bedrooms:
2
Bathrooms:
3
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 $299 per night (USD)
VRBO
$Low Rates for longer stays! Perfect Location! \nSteps to Beach!/Heated pool!$
From $204 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 $204 per night (USD)
Expedia
From $601 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 $601 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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 $432 per night (USD)
Expedia
From $444 per night (USD)
VRBO
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)
VRBO
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 $761 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 $761 per night (USD)
VRBO
From $630 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 $630 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Heron Heaven - 3 bedroom private pool home across street from beach - By Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
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 $482 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Dilly Dally by the Seas: 1 Block to Beach, Rooftop Deck, Pool & Spa by Anna Maria Life
Bedrooms:
4
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 $692 per night (USD)
Expedia
From $342 per night (USD)
VRBO
La Coconut: 1 Block to Beach! Dog Friendly! Ping Pong & Foosball, Heated Pool by Anna Maria Life
Bedrooms:
2
Bathrooms:
3
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 $342 per night (USD)
VRBO
From $663 per night (USD)
Expedia
5 bedroom canal home on AMI, heated pool, pet friendly!
Bedrooms:
3
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 $663 per night (USD)
Expedia
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
From $212 per night (USD)
Expedia
At Ease West: A tropical rental 1/2 block from the beach
Bedrooms:
1
Bathrooms:
2
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 $212 per night (USD)
Expedia
From $366 per night (USD)
VRBO
A Reel Beauty: 2 Blocks to Beach! Pool, Spa, Putting Green, by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
3
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 $366 per night (USD)
VRBO
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 $535 per night (USD)
VRBO
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 $535 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Cool Breeze by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking for the ultimate beachfront vacation experience? Look no further than Cool Breeze, a stunningly remodeled 2 bedr ...
From $474 per night (USD)
Expedia
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
From $469 per night (USD)
VRBO
Beautiful House
Bedrooms:
1
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
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VRBO
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
VRBO
From $850 per night (USD)
Expedia
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 $850 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Miller Time managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxury 4-Bedroom Island Getaway with Pool, Spa, and Game Room - Just Steps from Holmes Beach! Welcome to your dream vac ...
From $696 per night (USD)
VRBO
From $680 per night (USD)
VRBO
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 $680 per night (USD)
VRBO
From $1166 per night (USD)
VRBO
Grains of Sand by Beach Boutique Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Grains of Sand is a stunning custom home located directly across from the beautiful Gulf of Mexico. This home boasts alm ...
From $1166 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Relax by the pool, 4 bd/3.5ba, pool, beach gear!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome home to your tranquil retreat, where every corner beckons you to unwind and rejuvenate! Picture yourself curling ...
From $604 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Steps to the Beach, Private Half Duplex, Private Pool
Bedrooms:
2
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 $551 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Beautiful Private Half Duplex Steps from the Beach
Bedrooms:
2
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 $541 per night (USD)
Expedia
From $380 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 $380 per night (USD)
VRBO
From $794 per night (USD)
VRBO
Comfortable vacation home directly on the beach and sunsets from the terrace
Bedrooms:
2
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 $794 per night (USD)
VRBO
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $362 per night (USD)
VRBO
BEAUTIFUL 3/2 TOWNHOME w/ HEATED PRIVATE POOL. STEPS FROM THE GULF BEACHES!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! Welcome to your Anna Maria Island vacation! You will enjoy your time at thi ...
From $362 per night (USD)
VRBO
From $286 per night (USD)
Expedia
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 $286 per night (USD)
Expedia
From $491 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 $491 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Stillpoint: Heated pool, 2-min walk to beach, sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Photos updated March 2025 Welcome to the graceful beauty of Stillpoint, an island retreat for family and friends just s ...
From $554 per night (USD)
Expedia

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