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 $536 per night (USD)
VRBO
Beachfront - Sandy Turtle by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $536 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Anna Maria - Holmes Beach - 3BD 2BTH Home - PRIVATE HEATED POOL - WALK TO BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AZURE BLISS ! _____ SEE VIDEO TOUR - https://youtu.be/_qqC8sHY85c The incredible location mixed in with all of the ...
From $573 per night (USD)
Expedia
From $128 per night (USD)
VRBO
RELAX/WORK @ Sunbow Bay! By Beach w/Pools & Pickleball. Clean & newly updated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Great location!....6 minute walk to the beach, trolley stop in front with Publix across the street. Enjoy this beautifu ...
From $128 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Beautiful 1 Bedroom Condo with Beach Facing Balcony and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #112 by Anna Maria Vacations 100 73rd Street, Unit #112, Holmes Beach, Florida VRC21-000175 Your d ...
From $566 per night (USD)
Expedia
From $542 per night (USD)
VRBO
Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Discover Mango Bay, A Stunning Coastal Home Designed For ...
From $542 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Golf Cart, Dream Weaver by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $582 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Tropical Anna Maria Island Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Privacy with close stroll to the beach! Beautiful Anna Maria Island Vacation Villa. Sleeps 6 in 3 bedrooms, with 2 ful ...
From $534 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Plumeria Villa by Beach Boutique Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Plumeria Villa at Island Garden Villas, where Old Florida charm meets stylish modern luxury. *Features inclu ...
From $204 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Family Friendly Home with Pool, 4 mins to Beach! - Starfish Cove, B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, B by AMI Locals 7802 Palm Dr, Unit B, Holmes Beach, FL 34217 VRC21-000189 Welcome to Starfish Cove, B, ...
From $199 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Dog-Friendly Home with Pool! 4 mins to the Beach - Starfish Cove, A
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, A by AMI Locals 7802 Palm Dr, Unit A, Holmes Beach, FL 34217 VRC17-000165 Welcome to Starfish Cove, A, ...
From $200 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Kiwi Cabana by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Kiwi Cabana! A 2 bed/2 bath, totally private half duplex with a large heated pool in the heart of Holmes Beac ...
From $301 per night (USD)
VRBO
Click For Pricing
Expedia
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
Click For Pricing
Expedia
$The Palms \A\ an upstairs unit located in the center district of Holmes Beach$
From $203 per night (USD)
VRBO
The Palms \"A\" an upstairs unit located in the center district of Holmes Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy this upstairs condo unit consisting of 2b/1ba, living, dining area & kitchen with enough sleeping for 6. Condomin ...
From $203 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Tidal Daze! Pool, Putting Green & Beach Walk!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Tidal Daze by AMI Locals Holmes Beach Vacation Home with Private Pool and Putting Green VRC22-000087 Welcome to Tida ...
From $681 per night (USD)
Expedia
From $203 per night (USD)
VRBO
WBC 212 Spacious 2/2 Pool Tennis Condo Close To White Sand Beach Shopping
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRC20-000174 Westbay Cove 212 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious two bedroo ...
From $203 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Two great beach accesses just steps away!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VRC16-000098 Welcome to The Palms #3 just steps away from beautiful Holmes Beach. Also just steps away are shops, a groc ...
From $231 per night (USD)
Expedia
From $441 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $441 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom / 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. VRC16-000069 Max 1 veh ...
From $409 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom/2 Bath gulf front,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745 Beach/Gulf Front - Com ...
From $416 per night (USD)
VRBO
From $409 per night (USD)
Expedia
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $409 per night (USD)
Expedia
From $378 per night (USD)
VRBO
217 84th - Anna Maria Island- Private home 3 Bedroom/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $378 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC20-000254 ...
From $401 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath gulf...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Gulf/Beach Fr ...
From $383 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Beach Bliss managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
🌴 Beach Bliss by Beach Retreats Vacation Rentals 📍 320 64th Street, Holmes Beach, FL 34217 🏡 3 Bedrooms | 3 Bathrooms ...
From $459 per night (USD)
Expedia
From $617 per night (USD)
VRBO
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 $617 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Distan ...
From $234 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...
From $471 per night (USD)
VRBO
From $228 per night (USD)
Expedia
266 S. Harbor - Anna Maria Island- Private home 3 Bedroom/ 2 Bath , maximum...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
266 South Harbor - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC# 20-000032 No Pool - ...
From $228 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $339 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Just a few short blocks with no busy roads to cross to get to the beach. The home is very spacious with 4 bedrooms. Th ...
From $495 per night (USD)
Expedia
From $198 per night (USD)
VRBO
3 Bed/3 Bath Ground Floor Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy this spacious updated condo in a beautifully landscaped, quiet Bayside complex with heated pool and private pickle ...
From $198 per night (USD)
VRBO
From $1135 per night (USD)
Expedia
Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Copy this link to your browser to see 3D view of Emerald Seas floor plan: https://www.zillow.com/view-3d-home/d7fdf4d1- ...
From $1135 per night (USD)
Expedia
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $277 per night (USD)
VRBO
Anna Maria Island \"Star Fish\"Condo & Boat Slip-2BR-2BA-Sleeps4
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Starfish Condo on Anna Maria Island -2 BR 2 BA With a 25' Boat Slip Wonderful quiet residential area overlooks pool; bey ...
From $277 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom/ 3 Bath, maximum...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sandy Pointe 114 - Anna Maria Island - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. VRC16-000070 Di ...
From $369 per night (USD)
Expedia
From $691 per night (USD)
VRBO
September Golf Cart Special
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 $691 per night (USD)
VRBO
From $619 per night (USD)
Expedia
For Shore: Sleeps 10, steps to beach, heated pool!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
***Photos Updated September 2025*** If you are hoping to stay on the perfect Old Florida island in the perfect beach ho ...
From $619 per night (USD)
Expedia
From $657 per night (USD)
VRBO
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $657 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Hibiscus Villa by Beach Boutique Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Hibiscus Villa at Island Garden Villas, where Old Florida charm blends effortlessly with stylish modern luxur ...
From $217 per night (USD)
Expedia
From $1047 per night (USD)
VRBO
510 Bayview - Anna Maria Island - Private home 5 Bedroom / 5 Bath with...
Bedrooms:
5
Bathrooms:
5
Sleeps:
6
510 Bayview - Anna Maria Island - 5 Bedroom / 5 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - ...
From $1047 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Orchid Villa by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Orchid Villa at Island Garden Villas, where coastal elegance meets tropical serenity. *Features include* * ...
From $331 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Distan ...
From $314 per night (USD)
VRBO
From $318 per night (USD)
Expedia
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath , maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC19-000138 Community ...
From $318 per night (USD)
Expedia
From $713 per night (USD)
VRBO
Mermaid's Crossing managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
210 65th Street Holmes Beach, FL 34216 VRC17-000007 NO CANCELATION FEES Cancellation Policy (Effective for reservations ...
From $713 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Bluetique: Monthly luxury beach home, private pool, rooftop deck
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Bluetique is the perfect place for an extended getaway! The large lot provides plenty of space indoors and out. Bluetiqu ...
From $532 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by Anna Maria Life Vacation Rentals 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $344 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Florida Breeze: Pool home in perfect central location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $442 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Windshore A! - ~200 Steps to the Beach, Private Heated Pool, Beach Items, Wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fully renovated in 2025, our Windshore A leaves no wishes open when it comes to your vacation on Anna Maria Island. Only ...
From $433 per night (USD)
VRBO
From $291 per night (USD)
Expedia
(2) Bedroom (2) Bath with Private 10' x 30' Sun Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre " ...
From $291 per night (USD)
Expedia
From $954 per night (USD)
VRBO
Multi-family Luxury Villa at its Finest! Pool, Spa, Mini golf and more! Close to
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Island Life Villa by AMI Locals Luxury Bayfront Retreat on Anna Maria Island VRC20-000313 Photos taken May 2025. High ...
From $954 per night (USD)
VRBO
From $421 per night (USD)
VRBO
Turtle Nest! Private Heated Pool and Access to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $421 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Home with Private Outdoor Living Space, Community Pool - Sea La Vie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by AMI Locals Condo in Holmes Beach, Florida VRC21-000203 Welcome to Sea La Vie! This three-bedroom, three- ...
From $336 per night (USD)
VRBO
From $249 per night (USD)
Expedia
The Villas 3A in Holmes Beach - 1BR Condo with Pool - By Island Real Estate Vaca
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
“The Villas 3A” is a one bed one bath villa that’s has both the amenities and location to make for a perfect stay on Ann ...
From $249 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Anthony Beach Cottages - Bare Feet Retreat - 2 bedroom pool cottage - Sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Florida home backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably ...
From $162 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Seahorse Cottage! Walk to Beach & Shops!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seahorse Cottage by AMI Locals Home in Holmes, Beach Florida VRC16-000110 Enjoy a luxury vacation with friends and fami ...
From $602 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Great Island Getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful 2 BR/2 BA condo is all about charm and comfort. You will have no problem leaving your cares behind and en ...
From $451 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Coconuts Beachfront #109 by AMI Locals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #109 by AMI Locals 100 73rd St Unit 109 - Holmes Beach, FL 34217 Welcome to Coconuts Beachfront # ...
From $321 per night (USD)
Expedia
From $156 per night (USD)
VRBO
1-bedroom condo just a short walk to Anna Maria Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Holmes Beach's delightful coastal town offers you a fantastic stay at our cozy 1-bedroom condo. Nestled just a short wal ...
From $156 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Serene coastal condo with easy beach access, water views, pool, WiFi & porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beach & Gulf Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $326 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Island Time: Gulf front condo 20 ft to the beach with shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $382 per night (USD)
VRBO
Click For Pricing
Expedia
Amazing Resort Sixty-Six, 1 Bedroom Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
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 Pricing
Expedia
From $311 per night (USD)
VRBO
Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Isle Haven B will let you make beautiful memories - it's the perfect beach getaway to relax and enjoy the classic Florid ...
From $311 per night (USD)
VRBO
From $892 per night (USD)
Expedia
⚓ Newly Renovated!, Private pool home 5 min> walk to beach!⚓🐕🏖🌅
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Sweet Home Anna Maria! ⚓Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! ⚓Private ...
From $892 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Egret at Blue Lagoon on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $292 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Private 3BR Heated Pool Villa - Sea Glass on Anna Maria - By Island Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
When you arrive at “SeaGlass” you are greeted with pleasant landscaping, a gorgeous brick driveway, and an adorable home ...
From $376 per night (USD)
Expedia
From $407 per night (USD)
VRBO
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 $407 per night (USD)
VRBO
From $696 per night (USD)
VRBO
TRUE BEACHFRONT HOME DIRECTLY ON SUGAR WHITE SANDS WITH HEATED POOL - IDYLLIC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
IN THE EVENT OF A MANDATORY EVACUATION DUE TO A STORM/HURRICANE ALL GUESTS WILL RECEIVE A FULL REFUND. Gaze Vacations ...
From $696 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wifi, Steps to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Dragonfly Breeze, a 3 bedroom and 2 bathroom elevated private pool home located in Holmes Beach, just a short ...
From $425 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Summer Wind- An island getaway in the perfect location.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $432 per night (USD)
Expedia
Click For Pricing
VRBO
Island Time – Coastal Home w/ Lagoon-Style Pool & Spa, Short Walk to Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Island Time! On Anna Maria Island (Holmes Beach, FL) Island Time is a Spacious Coastal Retreat with a Privat ...
Click For Pricing
VRBO
From $504 per night (USD)
Expedia
One block to beach! 3 bedroom home with pool and backyard oasis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Walking on Sunshine by AMI Locals Home in Holmes Beach, Florida VRC19-000232 Your dream vacation awaits at Walking on S ...
From $504 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $277 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Anna Maria Home with Private Pool, Near the Beach! - Coveside Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coveside Cottage by AMI Locals Holmes Beach Family Retreat with Private Pool VRC19-000006 Welcome to Coveside Cottage ...
From $377 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Cute 3/2 Cottage close to Beach and centrally located.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC21-000048 Swizzle On The Sound is just a short stroll to the beautiful beaches of Anna Maria Island from your own pi ...
From $295 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Waters Edge 104S by Duncan Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Water's Edge 104S! This beautiful two bedroom, two bath condo that is located in the Water's Edge Complex whi ...
From $537 per night (USD)
Expedia
From $743 per night (USD)
VRBO
Book Swell Life: 4-Bedroom Paradise Steps from the Beach with Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Swell Life by AMI Locals Home in Holmes Beach, Florida VRC21-000150 Experience a slice of paradise at Swell Life, a ...
From $743 per night (USD)
VRBO
From $222 per night (USD)
Expedia
LOCATION!! Cabana just steps from the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Welcome to Anna Maria Island the # 1 spot for a perfect getaway. Bask in the tropical paradise of AMI with white sugar ...
From $222 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positi ...
From $430 per night (USD)
VRBO
From $1626 per night (USD)
Expedia
AMI’s Largest Rental, 4 kitchens, Spa, Heated Pool, Rooftop Deck.
Bedrooms:
8
Bathrooms:
10
Sleeps:
24
Large family or group rental. This unique property with 5 suites is great for families or groups. Each suite has its own ...
From $1626 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Salty Harbor AMI pool retreat near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Stunning Fall 2024 renovation completed! Charming Salty Harbor boasts a private heated pool and sits on a quaint corner ...
From $308 per night (USD)
VRBO
From $633 per night (USD)
Expedia
Large Beach Home 5 Houses from Sand! Heated Pool, Game Room, Sun Deck & Tiki Bar
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious 4BR/4BA Beach Home with Heated Pool, Tiki Bar, Game Room & Beach Gear Galore Welcome to your ultimate beach ge ...
From $633 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Enjoy the Island Life on Anna Maria Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The location is very quiet and private. It's a short walk to Holmes Beach, Duffy s Tavern, Hurricane Hanks, The Feast, ...
From $209 per night (USD)
VRBO
From $412 per night (USD)
Expedia
3 bedroom, on AMI, heated private pool, PET FRIENDLY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The family friendly Florida vacation you need is waiting at Mykonos! This Anna Maria Island beach rental has it all. Fro ...
From $412 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $769 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $329 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Crow's Nest Spinnakers Cottages: 250 Steps to Beach! Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Crow's Nest Spinnakers Cottages by Anna Maria Life Vacation Rentals 202 56th St. #2, Holmes Beach, FL 34217 What You'll ...
From $211 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Starfish Isle managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VRC 21-000046 5803 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one ...
From $439 per night (USD)
Expedia
From $595 per night (USD)
VRBO
Conch Out Beach House managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
🐚 Conch-Out Beach House 📍 303 68th St, Holmes Beach, FL 34217 📌 VRC19-000273 | 4 Bedrooms | 3 Bathrooms | Sleeps 8 | ...
From $595 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Starfish Cove managed by Beach Retreats FL Anna Maria Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
302 60th Street Holmes Beach, FL 34217 VRC19-000274 At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for y ...
From $426 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Sun Plaza West Unit 201, gulf front complex on AMI
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Important Update, Pool will be closed from July to Mid- September 2025* Come experience Unit 201 at Sun Plaza Wes ...
From $389 per night (USD)
VRBO
From $274 per night (USD)
Expedia
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $274 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $390 per night (USD)
VRBO
From $240 per night (USD)
Expedia
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $240 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Dog-friendly seaside home - heated private pool & spa, great location near beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $307 per night (USD)
VRBO
From $1002 per night (USD)
Expedia
Luxury beachside home with heated private pool - tranquil & close to everything
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Wine Down Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1002 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Waterfront condo with pool and easy access to sugar sand beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A Gulf Front Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $341 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Ocean-front condo with WiFi, pool & Gulf views - steps to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Martinique 401S Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $503 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Island-style townhome with WiFi & pool - minutes from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
North Beach Village 27 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $537 per night (USD)
VRBO
From $934 per night (USD)
Expedia
Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
3 Oars Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $934 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Chic Pool Home Steps to Beach! Game Room and Paddleboards
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pure Beach by AMI Locals 204 71st Street | Holmes Beach, Florida VRC21-000101 Welcome to Pure Beach, a bright and s ...
From $446 per night (USD)
VRBO
From $637 per night (USD)
Expedia
Large Single Level-1 Minute Walk To The Beach-5 minute walk to Restaurant/Shops
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Recently renovated with all new kitchens and more! Welcome to our Blue Grotto on the beautiful Anna Maria Island. We h ...
From $637 per night (USD)
Expedia

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