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 $304 per night (USD)
VRBO
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 $304 per night (USD)
VRBO
From $202 per night (USD)
Expedia
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 $202 per night (USD)
Expedia
From $493 per night (USD)
VRBO
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 $493 per night (USD)
VRBO
From $637 per night (USD)
Expedia
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 $637 per night (USD)
Expedia
From $433 per night (USD)
VRBO
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 $433 per night (USD)
VRBO
From $217 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 $217 per night (USD)
Expedia
From $430 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 $430 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 $266 per night (USD)
VRBO
Island villa with heated private pool, tranquil courtyard, easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $266 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
West Bay Point 12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $395 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Beautiful lakeside home w/ upscale amenities, heated private pool & fishing dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spectacular Saltwater Seas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $365 per night (USD)
VRBO
From $341 per night (USD)
Expedia
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 $341 per night (USD)
Expedia
From $459 per night (USD)
VRBO
Dog-friendly cottage w/ island views, shared pool & private patio - beach nearby
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Starfish Beach Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $459 per night (USD)
VRBO
From $1220 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 $1220 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Sea Palm Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $487 per night (USD)
VRBO
From $712 per night (USD)
Expedia
Oceanview getaway with pool & private patio - steps from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Palm Gables 106 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $712 per night (USD)
Expedia
From $175 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 $175 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Waterfront condo with furnished balcony overlooking the pristine beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Shores 205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $398 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Darling beachside villa w/ space & privacy - a cozy coastal florida experience
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Playa Casanas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $560 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Modern home near Gulf beaches with private heated pool & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Neolinda 305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $395 per night (USD)
Expedia
Click For Pricing
VRBO
Charming condo with heated pool - near beach, wetlands, & trolley stop
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For Pricing
VRBO
From $531 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 $531 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Tropical-themed getaway w/ heated private pool - walk to free trolley, shopping
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $307 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Hidden Cove Unit 6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $415 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Comfortable island villa with private heated pool, courtyard & easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa East Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $262 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Seaside family-friendly condo with WiFi, pool & prime location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serenity Now Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $192 per night (USD)
Expedia
From $497 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 $497 per night (USD)
VRBO
From $1012 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 $1012 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Chic Pool Home Steps to Beach | Game Room + Paddleboards
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pure Beach by AMI Locals Modern Island Escape with Saltwater Pool and Game Room 204 71st Street | Holmes Beach, Flori ...
From $481 per night (USD)
VRBO
From $621 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 $621 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Private Pool - Summer Breeze by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3 ...
From $418 per night (USD)
VRBO
From $287 per night (USD)
Expedia
One Bedroom Island Luxury Cottage located less than 2 blocks from the beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Flop Cottage located 1 block from the Gulf beaches of Anna Maria Island. Flop Cottage is a ground level half ...
From $287 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is in the monthly rental ...
From $1007 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Holmes Beach Family Home: Private Pool & 3 Decks!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Explore Florida’s beautiful Anna Maria Island from ‘Salty Dogs Beach House,’ a 3-bedroom, 2.5-bathroom, single family Ho ...
From $334 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Inviting Coastal Getaway w/ Easy Beach Access, Full Kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $222 per night (USD)
VRBO
From $717 per night (USD)
Expedia
Ground Floor Luxury Villa in Prime Location, Steps to Beach, Heated Pool/Spa
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Prime Location! VERY CLOSE TO BEACH!!! Luxurious ground level home located at 124 50th Street, Holmes Beach, in the „Gol ...
From $717 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Cabin 2 Spinnakers Cottages: Dog Friendly - 250 Steps to Beach Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cabin 2 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #2, Holmes Beach, FL 34217 What You'll Lov ...
From $194 per night (USD)
VRBO
From $960 per night (USD)
Expedia
BUENA VISTA LUXURY BEACHFRONT 4BR - Anna Maria Island - By Island Real Estate Va
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Top 10 Gulfview on Anna Maria Island!!! You can see for miles in both direction down the beach. Luxury condominium “Buen ...
From $960 per night (USD)
Expedia
From $972 per night (USD)
VRBO
DIRECT BEACH FRONT - Luxury 4BR Condo - Anna Maria Island- By Island Real Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
DIRECT BEACH FRONT - Luxury 4BR Condo - Buena Vista #3 - 101 67th Street - 4 Bedrooms and 3 and a 1/2 Baths - Bed/s: 3 ...
From $972 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Anna Maria Island Waterfront house with private pool, spa, elevator and dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaway ...
From $840 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Northshore Villa - 3 Bedroom, 2 Bathroom Vacation Rental Across from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come for the SUN, stay for the FUN!!! Find everything that makes a fun beach getaway on Anna Maria Island memorable whe ...
From $262 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Casual beachside getaway with pool, and easy beach access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Water's Edge 105 South Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $307 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Welcoming condo close to the beach with private heated pool & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LaMadeira 305 Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $421 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Upscale condo with large deck & shared pool - just steps from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
La Casa Karen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $502 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Quaint beachfront duplex in ideal location with screened lanai & free trolley
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Playa Casanas North Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $341 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Adorable beachfront rental in a great location with Gulf access right outside
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Playa Casanas South Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $283 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spend your Anna Maria Island vacation in five star luxury when you visit “Aquarius”. This fully renovated Holmes Beach v ...
From $430 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Breezy Harbor AMI pool retreat near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Stunning Fall 2024 renovation completed! Charming Breeze Harbor boasts a private heated pool and sits on a quaint corne ...
From $290 per night (USD)
Expedia
From $1779 per night (USD)
VRBO
Buena Vista #2: Luxury Beach Front Condo, Amazing Views, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Buena Vista #2 by Anna Maria Life Vacation Rentals 101 67th St #2, Holmes Beach, FL 34217 What You'll Love About This H ...
From $1779 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Modern Beach House, 1 Block from beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming Anna Maria Island Vacation Home is located just a few houses from the white sand beaches! Holmes Beach is ...
From $250 per night (USD)
Expedia
From $911 per night (USD)
VRBO
GLORIOUS DAZE Beach House POOL! SPA! GOLFCART! ELEVATOR! PUTTING GREEN!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Glorious Daze! Our four bedroom/four bath private home is located along the sugary white sands of beautiful H ...
From $911 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Caribbean Surf managed by Beach Retreats FL Anna Maria Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
306 67th Street Unit B Holmes Beach, FL 34217 VRC 19-000277 🏝 Caribbean Surf by Beach Retreats Vacation Rentals 📍 Hol ...
From $460 per night (USD)
Expedia
From $833 per night (USD)
VRBO
307 65th Street managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
🏖 Island Escape by Beach Retreats Vacation Rentals 📍 307 65th St, Holmes Beach, FL 34217 🏡 VRC18-000047 Your dream ge ...
From $833 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Breezy house with great location near beach, shopping & dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Guava Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $230 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Ground Floor Luxury Home, very close to Beach, Heated Pool/Spa 🌴🌴🌴🌴
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach 🌴🌴🌴🌴 Welcome to the AMI Beach Home on beautiful ...
From $511 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Getaway by Anna Maria Life Vacation Rentals 205 56th St., Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $350 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Gumbo Cottage located just 7 houses from the Gulf beaches of Anna Maria Island and a street away from downtow ...
From $395 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Beachfront Bliss at Bamboo Apartments #2– A Hidden Gem on Anna Maria Island!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hello, Guest! Welcome to Bamboo Apartments, Apartment #2, part of our family-owned five-unit beachfront retreat featur ...
From $295 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AT A GLANCE Beautiful 3-bedroom 3 bath homes West of Gulf Drive, a short stroll to the beach Gorgeous private heated wit ...
From $457 per night (USD)
VRBO
From $289 per night (USD)
Expedia
EXCELLENT LOCATION IN THE HEART OF HOLMES BEACH ON ANNA MARIA ISLAND!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Renovated in 2025, bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minu ...
From $289 per night (USD)
Expedia
From $279 per night (USD)
VRBO
View of Beach from the deck, Walk to all , free WIFI.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Immerse yourself in the ultimate Anna Maria Island getaway with this charming vacation rental just minutes away from th ...
From $279 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Beach View Retreat! 5BR Home with Pool, Spa, Rooftop Deck and Walk to Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beach View Retreat by AMI Locals Home in Holmes Beach, Florida VRC19-000046 Welcome to Beach View Retreat, a custom-bu ...
From $529 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Sun Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
**Beach House, Sleeps 4, Easy walk to beach, Shops & Restaurants** Beautiful cozy cottage conveniently located in the h ...
From $343 per night (USD)
VRBO
$Sandy Cheeks & Barefeet, Gorgeous Gulf beach Place, Summer\nspecials$
From $333 per night (USD)
Expedia
Sandy Cheeks & Barefeet, Gorgeous Gulf beach Place, Summer\nspecials
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf views from several rooms and lanai! Quick access (only 1 small house between you and sun & sand). 2 Bedroom, 2 Bath ...
From $333 per night (USD)
Expedia
From $254 per night (USD)
VRBO
1 Block To Beach! Convenient, Modern, Comfortable, Clean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Comfortable, convenient townhouse one block to beach and close to other attractions. 2BR/2BA with 1 BR and BA with showe ...
From $254 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Sunkissed by Duncan Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunkissed is a beautiful, elevated townhome located in Holmes Beach-just a short stroll to the gorgeous white sandy beac ...
From $458 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Sea Pirate 7 2/1 Condo Pool Just Steps To Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VRC16-000815 Sea Pirate Condo #7, located at 3301 Gulf Drive in the heart of Holmes Beach is just across the street fro ...
From $270 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Kickback Cabana managed by Beach Retreats FL Anna Maria Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
411 79th Street Holmes Beach, Fl 34217 VRC19-000189 NO CANCELATION FEES Cancellation Policy (Effective for reservations ...
From $538 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Island Retreat by SeaBreeze Vacation
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds an ...
From $168 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Lovely family condo with a private heated pool & Gulf view, close to the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Crab Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $395 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Relax at Bryant’s Beach Bungalow!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your getaway is only 400 steps from the beautiful beach! This spacious three-story home is designed for comfort, conveni ...
From $411 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The cozy front porch of Gulf Winds B invites you to have your morning coffee or your evening cocktail and in the back ya ...
From $233 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Beach Potato: Gulf View Condo, Pool, Steps to the beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beach Potato by Anna Maria Life Vacation Rentals 3404 Gulf Drive, #5, Holmes Beach, FL 34217 What You'll Love Ab ...
From $204 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Barefoot Dreams: Dog Friendly, Private Pool,1 Block to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Barefoot Dreams by Anna Maria Life Vacation Rentals 201 76th St. East Unit B, Holmes Beach, FL 34217 What You'll Love A ...
From $248 per night (USD)
Expedia
From $719 per night (USD)
VRBO
Beach Dance in Holmes Beach
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Beach Dance is the perfect family home in a convenient location just steps to the Gulf, Restaurants, Shops and the Free ...
From $719 per night (USD)
VRBO
From $315 per night (USD)
Expedia
BeachView Condo #8 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Beach View Condominum, #8 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 7 people. VRC22-000101 Co ...
From $315 per night (USD)
Expedia
From $288 per night (USD)
VRBO
2 minute walk to the beach! Off the main road in a quiet and tropical setting
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
What you'll love about this home: - Location! 2 min walk to the beach - 3 Bedrooms / 2 full bathrooms - 1 King, 1 Que ...
From $288 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Weekly Discounts! Exceptional Rating-A Pearl of a Beach Home- private pool & spa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical rear yard with private luxury heated Saltwater pool and hot tub/spa and spacious paved area plus large ground f ...
From $440 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cottage By the Sea is a (no smoking) Unit within the charming Sea Pirate condo complex located on a tranquil and des ...
From $253 per night (USD)
VRBO
From $296 per night (USD)
Expedia
SS Salamander North | Steps to the Beach + Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
VRC16-000499 Your Cozy Island Getaway in Holmes Beach Just one block from the sugar-white sands of the Gulf, SS Salaman ...
From $296 per night (USD)
Expedia
From $329 per night (USD)
VRBO
★ Spacious Condo ★ Steps to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Very private! Spacious 2 bedroom 2 full bath condo is just steps to Holmes Beach beach. Ocean view from your unit with t ...
From $329 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Your Own Oasis: A Tropical Retreat with Lagoon Style Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Own Oasis - An Island Retreat with Lagoon Style Pool, close to Bay and Beach Escape to "Your Own Oasis" on Anna Ma ...
From $329 per night (USD)
Expedia
From $663 per night (USD)
VRBO
She's Always Right - Pet Home w/ Pool, Spa, Steps to Beach & Prime AMI Location
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to She's Always Right! On Anna Maria Island (Holmes Beach, FL) Experience Island Luxury at She's Always Right, ...
From $663 per night (USD)
VRBO
From $753 per night (USD)
VRBO
Water Front/Heated Pool/Dock/Walk To Beach/Self Check In-Out/High cleaning/WiFi.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama ...
From $753 per night (USD)
VRBO
From $598 per night (USD)
VRBO
Direct Beach Front, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**ASK ABOUT LAST-MINUTE DEALS! Stay DIRECTLY on the beach in this gorgeous two-bedroom, two-bath condo! Our ...
From $598 per night (USD)
VRBO
From $335 per night (USD)
Expedia
2 Bedroom / 2 Bath Ground Level With a Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for a Weekly rental located in the heart of Anna Maria Island at 305 61st St, Unit A, Holmes Beach, FL, ...
From $335 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Coastal Chic Waterfront Condo Anna Maria Island Westbay Point 195 Holmes Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the charm of Anna Maria Island and its relaxed coastal lifestyle, just minutes from the beach. Enjoy fishing, ...
From $296 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Beautiful home with fenced yard, heated pool, hot tub, and elevator!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sand Castle by Anna Maria Island Accommodations Holmes Beach, FL 34217 VRC19-000022 Welcome to Sand Castle! Nestled in ...
From $624 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Bamboo Breeze! Cozy Pool Retreat Near Shops!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bamboo Breeze by Anna Maria Island Accommodations 203 70th Street, Unit B (East Unit), Holmes Beach, Florida VRC16-00 ...
From $281 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Holmes Beach Condo with Pool and Balcony! 3 Minutes to Beach - Seabreeze D
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seabreeze D by Anna Maria Island Accommodations 403 39th Street Unit D, Holmes Beach, Florida 34217 VRC16-000111 Welco ...
From $197 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Simply Chic 1.5 Blocks to Beach Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beaut ...
From $455 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Gulf Breeze Villa B by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000146 Gulf Breeze Vill ...
From $271 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Tropical Pool, Sunset Views, Game Room - It's a Jungle Out There
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
It's a Jungle Out There by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC19-000173 It’s a Ju ...
From $736 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Holmes Beach Vacation Home with Pool, Ping Pong, and Tiki Bar! 6 minutes to Beac
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Banana Cabana by Anna Maria Island Accommodations 318 64th Street, Holmes Beach, Florida 34217 Relax and unwind at Ban ...
From $330 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Ground-level AMI Condo Near the Beach! Large heated pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Palm Cay 6 by Anna Maria Island Accommodations Holmes Beach Beachside Condo VRC16-000127 Welcome to Palm Cay 6, a cha ...
From $256 per night (USD)
VRBO
From $711 per night (USD)
Expedia
Luxury home with Pool, Spa, and Dock -Bayshores
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayshores by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC18-000040 Welcome to Bayshores, a breat ...
From $711 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Home with Private Pool and Hot Tub! 3 Blocks to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sand Dollar by Anna Maria Island Accommodations Holmes Beach Private Pool & Hot Tub with Bay and Beach Access VR16-000 ...
From $335 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Condo with Pool! Near the Beach, Shops, and Dining! - Seabreeze A
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seabreeze A by Anna Maria Island Accommodations Holmes Beach Family-Friendly Beach Retreat VRC16-000112 Welcome to Se ...
From $190 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Beach Cottage! Walk to Dining, Shops and Island Trolley Stop
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beach Cottage by Anna Maria Island Accommodations 211 71st St Holmes Beach, FL 34217 VRC16-000178 Welcome to Beach C ...
From $424 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sun Daze by Anna Maria Island Accommodations 126 51st St, Unit B Holmes Beach, FL 34217 VRC16-000103 Discover the perfe ...
From $326 per night (USD)
Expedia

Search Your Destination Now!

Holmes Beach Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals