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 $339 per night (USD)
VRBO
Castnetter Beach Resort 5
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $339 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Anna Maria by the Bay (30 day minimum)
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully furnished bayside condo with gorgeous relaxing view. End unit, many windows let the sights in from every an ...
From $194 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Angel Sea managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
VRC19-000188 Stay at Angel Sea: Your Perfect Anna Maria Island Vacation Home Escape to Angel Sea—an idyllic 6-bedroom, ...
From $894 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Casa Sierra 203B - 2BR Condo with Pool - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. Th ...
From $324 per night (USD)
Expedia
From $893 per night (USD)
VRBO
Paradise Found managed by Beach Retreats FL Anna Maria Island
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
401 42nd Street Holmes Beach, FL 34217 VRC17-000010 Book with confidence: You may cancel your reservation up to 60 days ...
From $893 per night (USD)
VRBO
$Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations$
From $441 per night (USD)
Expedia
Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
“The Coconuts Beach Resort 108” is a 1 bed 1 bath beach front condo, nestled in the heart of Holmes Beach. Apart of the ...
From $441 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Chapter 2: Renovated pool home, tiki hut and close to beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Chapter 2 Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater p ...
From $417 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Adorable cottage just across the street from the beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Coconut Cottage #2 By AMI Locals Condo in Holmes Beach, FL Located across the street from the Manatee Public Beach! Hi ...
From $363 per night (USD)
Expedia
$6 BR\/5.5 Bth-Huge Heated Pool\/Spa\/Water Slide,,NO STORM DAMAGE! -1 Min Beach Wlk$
From $1071 per night (USD)
VRBO
6 BR\/5.5 Bth-Huge Heated Pool\/Spa\/Water Slide,,NO STORM DAMAGE! -1 Min Beach Wlk
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Featuring 6 bedrooms (sleeps 14), 5.5 baths and a fantastic location...NO STORM DAMAGE!!! - just a 1 minute walk to the ...
From $1071 per night (USD)
VRBO
From $598 per night (USD)
Expedia
🌴”Kiwi Cottage at Holmes Beach” - Private Heated Pool +Spa+Walk to the Beach! 🌞
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kiwi Coastal Cottage is under new ownership and every space has been thoughtfully redecorated with a cozy coastal island ...
From $598 per night (USD)
Expedia
From $760 per night (USD)
VRBO
Island Retreat- Stunning 4 bedroom with private heated pool and walk to beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
At A Glance Luxury Island style home Two minute stroll to the beach Tropical heated pool/Tiki Bar West-facing, view of ...
From $760 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Two bedroom1 bath unit with pool Steps to the beach. Great location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a futon sleeper sofa. Unit 20 ...
From $260 per night (USD)
Expedia
From $1062 per night (USD)
VRBO
Blue Water View- 6 bedrooms with amazing rooftop deck and private heated pool
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
At A Glance On our Professional Linen Service Program Beautiful Gulf water views, only 1 minute walk to the beach-locat ...
From $1062 per night (USD)
VRBO
From $1039 per night (USD)
Expedia
Pool and Beach Access: Ultimate Friends Getaway! - Coconuts Gulf View #117
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf View #117 by AMI Locals Condo in Holmes Beach, FL Coconuts Gulf View #117 is the ultimate spot for a fri ...
From $1039 per night (USD)
Expedia
$Sunny 3BR\/3BA Home. 8 Houses from Beach. Two Master Suites.$
From $361 per night (USD)
VRBO
Sunny 3BR\/3BA Home. 8 Houses from Beach. Two Master Suites.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Private single family home on a quiet side street, 8 houses from the beautiful world-class beaches of Anna Maria Island. ...
From $361 per night (USD)
VRBO
From $1099 per night (USD)
Expedia
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
A Pirate’s Dream by AMI Locals Home in Holmes Beach, Florida This grand, waterfront, four-bedroom, and three-and-a-ha ...
From $1099 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Beautifully updated home, moments from the beach with beach gear and Grill!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
We call this Home Beach Beauty for good reason! This beautiful home is West of Gulf Drive and only 175 steps to the beac ...
From $389 per night (USD)
VRBO
From $1018 per night (USD)
Expedia
2nd floor Condo with Beach and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals Condo in Holmes Beach, Florida VRC21-000172 Let the good times roll at Coconu ...
From $1018 per night (USD)
Expedia
From $362 per night (USD)
VRBO
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $362 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Bird of Paradise by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Bird of Paradise is a tr ...
From $421 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Palm Villa by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Palm Villa at Island Garden Villas, where Old Florida charm meets refreshing modern luxury. *Features includ ...
From $429 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Island Vibe 3: Close to Beach with Private Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Rent with attached duplex Island Vibe 2 (VRBO# 1193410) if you need 5 bedrooms! Welcome to Island Vibe 3, a renovated 2 ...
From $380 per night (USD)
Expedia
$Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach$
From $472 per night (USD)
VRBO
Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...
From $472 per night (USD)
VRBO
From $785 per night (USD)
Expedia
La Casa Costiera Blue Water - Newly Renovated, Top Floor Beachfront Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NOTE: the elevator at this property are currently not available. AT A GLANCE: - La Casa Costiera Unit #6 Blue Water - ...
From $785 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Waterfront Paradise In The Exclusive Neighborhood Of Key Royale
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
IMPORTANT: If calendar shows dates being available, but no quote is generated, please send us a message by selecting the ...
From $453 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $524 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Charming, Family Friendly Newly Renovated Duplex on Holmes Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our newly remodeled 2beds/2bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Ann ...
From $313 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Charming, Family Friendly Newly Renovated Duplex on Holmes Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our newly remodeled 2beds/2bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Ann ...
From $315 per night (USD)
Expedia
$BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets$
From $476 per night (USD)
VRBO
BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $476 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Water-view condo near the beach with pools, dock, pickleball - dog-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $235 per night (USD)
Expedia
From $608 per night (USD)
VRBO
Manatee Watch: Beautiful Waterfront Home, Hot Tub, 3 Min Walk to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Address of Manatee Watch: 205 N Harbor Drive, Holmes Beach, FL 34217 beautifulannamaria@yahoo.com MANATEE WATCH - A mar ...
From $608 per night (USD)
VRBO
From $703 per night (USD)
Expedia
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 $703 per night (USD)
Expedia
$Anna Maria \/ Holmes Beach - 3BD 2BTH Home - Private Heated Pool - Near beach$
From $408 per night (USD)
VRBO
Anna Maria \/ Holmes Beach - 3BD 2BTH Home - Private Heated Pool - Near beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
AZURE BLISS ! _____ SEE VIDEO TOUR - https://youtu.be/_qqC8sHY85c The incredible location mixed in with all of the ...
From $408 per night (USD)
VRBO
$RELAX\/WORK @ Sunbow Bay! By Beach w\/Pools & Pickleball. Clean & newly updated!$
From $153 per night (USD)
Expedia
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 $153 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Gulf Front 1 Bedroom Condo - Amazing Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconuts Beachfront #112 Condo in Holmes Beach, Florida VRC21-000175 Your dream beach vacation awaits at Coconuts Beach ...
From $747 per night (USD)
VRBO
$Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room$
From $800 per night (USD)
Expedia
Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) 3,000 sqft of a Beautifully Restored Island Home with Poo ...
From $800 per night (USD)
Expedia
Click For Pricing
VRBO
Tropical Anna Maria Island Villa
Bedrooms:
3
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 ...
Click For Pricing
VRBO
From $386 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 $386 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Kiwi Cabana by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PLEASE NOTE: This home is currently undergoing a full renovation. The current pictures include furniture and decor that ...
From $506 per night (USD)
VRBO
From $1078 per night (USD)
Expedia
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
3
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 ...
From $1078 per night (USD)
Expedia
$The Palms \A\ an upstairs unit located in the center district of Holmes Beach$
From $195 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 $195 per night (USD)
VRBO
$WBC 212 Spacious 2\/2 Pool Tennis Condo Close To White Sand Beach Shopping$
From $214 per night (USD)
Expedia
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 $214 per night (USD)
Expedia
From $529 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $529 per night (USD)
VRBO
$Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $392 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 $392 per night (USD)
Expedia
$Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom\/2 Bath gulf front,...$
From $549 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 $549 per night (USD)
VRBO
From $372 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 $372 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Sun Plaza West 105 - Two Bedroom condo, Sleeps 6- on the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AT A GLANCE Recently remodeled gulf front condo 2 Bedrooms and 2 Bathrooms with two balconies Complex equipped with a l ...
From $443 per night (USD)
VRBO
$217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...$
From $254 per night (USD)
Expedia
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 $254 per night (USD)
Expedia
$Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $402 per night (USD)
VRBO
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 $402 per night (USD)
VRBO
$Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide$
From $1127 per night (USD)
Expedia
Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...
From $1127 per night (USD)
Expedia
$Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath gulf...$
From $397 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 $397 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Beach Bliss managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Incredible 3-Bedroom, 3-Bathroom Bungalow Minutes from Anna Maria Island Beach - Your Private Backyard Oasis Awaits! We ...
From $553 per night (USD)
Expedia
From $172 per night (USD)
VRBO
White Palm-2 bedroom monthly condo getaway awaits you with beautiful bay views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
At a Glance Newly redecorated condo located on the northeastern Bayfront of Anna Maria Island 2 bedrooms and 2 bathro ...
From $172 per night (USD)
VRBO
From $829 per night (USD)
Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $829 per night (USD)
Expedia
$Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $243 per night (USD)
VRBO
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 $243 per night (USD)
VRBO
$Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...$
From $306 per night (USD)
Expedia
Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sandy Point Cove 112 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000138 Distance ...
From $306 per night (USD)
Expedia
From $525 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 $525 per night (USD)
VRBO
$Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...$
From $403 per night (USD)
Expedia
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 $403 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
4
Bathrooms:
5
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 $529 per night (USD)
VRBO
$3 Bed\/3 Bath Ground Floor Condo$
From $197 per night (USD)
Expedia
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 $197 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Anna Maria Island Sunshine Kiss Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, an ...
From $250 per night (USD)
VRBO
From $1287 per night (USD)
Expedia
Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!
Bedrooms:
6
Bathrooms:
7
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 $1287 per night (USD)
Expedia
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $221 per night (USD)
VRBO
Anna Maria Island \"Star Fish\"Condo & Boat Slip-2BR-2BA-Sleeps4
Bedrooms:
2
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 $221 per night (USD)
VRBO
$Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom\/ 3 Bath, maximum...$
From $375 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 $375 per night (USD)
Expedia
From $1090 per night (USD)
VRBO
Silver Surf- A stunning family home 2 blocks from the beach.
Bedrooms:
4
Bathrooms:
6
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 $1090 per night (USD)
VRBO
From $923 per night (USD)
Expedia
For Shore: Sleeps 10, steps to beach, heated pool!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
If you are hoping to stay on the perfect Old Florida island in the perfect beach home, you have found your destination a ...
From $923 per night (USD)
Expedia
From $697 per night (USD)
VRBO
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $697 per night (USD)
VRBO
From $364 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 $364 per night (USD)
Expedia
$510 Bayview - Anna Maria Island - Private home 5 Bedroom \/ 5 Bath with...$
From $1049 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 $1049 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Orchid Villa by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Orchid Villa at Island Garden Villas, where coastal elegance meets tropical serenity. *Features include* * ...
From $451 per night (USD)
Expedia
$Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $310 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 $310 per night (USD)
VRBO
$LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath , maximum...$
From $332 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 $332 per night (USD)
Expedia
From $773 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 Book with confidence: You may cancel your reservation up to 60 days ...
From $773 per night (USD)
VRBO
Click For Pricing
Expedia
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...
Click For Pricing
Expedia
From $388 per night (USD)
VRBO
Seaside Beach House 203 | Gulf-Front Escape with Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
VRC20-000296 Wake up to breathtaking Gulf views and fall asleep to the sound of the waves at Seaside Beach House 203, a ...
From $388 per night (USD)
VRBO
From $427 per night (USD)
Expedia
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
Bedrooms:
3
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 $427 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Florida Breeze: Pool home in perfect central location!
Bedrooms:
3
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 $602 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $336 per night (USD)
VRBO
(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 $336 per night (USD)
VRBO
From $1165 per night (USD)
Expedia
ISLAND LIFE VILLA is Luxury at it's Finest! Incredible Water Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
*During high season, we currently rent Saturday – Saturday. Please adjust your date range or contact our reservations of ...
From $1165 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Blue Agave Villa by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Blue Agave Villa is a tr ...
From $397 per night (USD)
VRBO
$Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach$
From $586 per night (USD)
Expedia
Turtle Nest! New Holiday House w\/ Pool, Wifi, 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 $586 per night (USD)
Expedia
From $295 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 $295 per night (USD)
VRBO
From $162 per night (USD)
Expedia
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)
Expedia
From $574 per night (USD)
VRBO
Charming Private Home, Private Pool and Spa. Fenced Yard, Updates Throughout
Bedrooms:
4
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 $574 per night (USD)
VRBO
From $169 per night (USD)
Expedia
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 $169 per night (USD)
Expedia
From $184 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 $184 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Island Time: Gulf front condo 20 ft to the beach with shared pool
Bedrooms:
2
Bathrooms:
2
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 $386 per night (USD)
Expedia
From $470 per night (USD)
VRBO
WONDERFUL BEACH VIEWS AND LARGE POOL!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
4200 Gulf Drive, Holmes Beach, Anna Maria Island Gulf Sands # 203 ... Beautiful views of the gulf from this updated 2 b ...
From $470 per night (USD)
VRBO
Click For Pricing
Expedia
Resort Sixty-Six, Holmes Beach, Florida, 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 $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
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 $282 per night (USD)
VRBO
Closer to the beach does not work: comfortable apartment at ground level on the beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ATTENTION: We rent with 1 week minimum: Saturday to Saturday Old Florida Feeling: bungalow right on the beach on level - ...
From $282 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!
Bedrooms:
2
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 $308 per night (USD)
Expedia
From $840 per night (USD)
VRBO
⚓Now Booking for Summer! Newly Renovated!, Private pool home 5 min> walk to beach!⚓🐕🏖🌅
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Sweet Home Anna Maria! ⚓Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! ⚓Private ...
From $840 per night (USD)
VRBO
From $157 per night (USD)
VRBO
Carissa Beach House: No more in business thanks to Helene and Milton.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Carissa Beach House is a vacation rental on Anna Maria Island (between Tampa & Sarasota), situated about 350 steps from ...
From $157 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Private 3BR Heated Pool Villa - Sea Glass on Anna Maria - By Island Real Estate
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
When you arrive at “SeaGlass” you are greeted with pleasant landscaping, a gorgeous brick driveway, and an adorable home ...
From $586 per night (USD)
Expedia
From $588 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 $588 per night (USD)
VRBO
From $790 per night (USD)
Expedia
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Highlights: -large bay of windows perfectly frame the beach from the kitchen, living, and dining areas -Screened porch - ...
From $790 per night (USD)
Expedia

Search Your Destination Now!

Holmes Beach Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals