Holmes Beach Rentals
From $100 per night (USD)HomeAway
The Beautiful Cove - Luxury 2 bed 2 bath apartment close to beach and amenities
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully 2019 decorated condo is set in a peaceful private setting amongst the natural beauty of Anna Maria isla ...
From $100 per night (USD)HomeAway
From $335 per night (USD)VRBO
Unique Lighthouse by AMIBeachClub Arrive any day May! Grab your swimsuit and go!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
A beacon of outstanding design, Anna Maria Island's newest landmark, The Lighthouse, is located at 6807 Palm Drive, Holm ...
From $335 per night (USD)VRBO
From $288 per night (USD)HomeAway
Comfortable vacation home directly on the beach and sunsets from the terrace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
We have found our perfect spot on the beach. After visited the resorts and beaches of Florida for many years we are here ...
From $288 per night (USD)HomeAway
From $25 per night (USD)VRBO
120 m² condominium with nice afternoon sun
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
The luxury condominium is located in Holmes Beach. The house is fully furnished and has 2 balconies, one behind full scr ...
From $25 per night (USD)VRBO
From $166 per night (USD)HomeAway
Egret's Landing - A private pool home, only minutes to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The comfort in Egret's Landing is stunning. The home is fully equipped with everything you need like a full kitchen with ...
From $166 per night (USD)HomeAway
From $120 per night (USD)VRBO
Townhouse/ 125 Steps to the Gulf of Mexico
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Anchors West, located in a quiet and convenient location. Whether you want to stroll to the beach or to shopping and re ...
From $120 per night (USD)VRBO
From $334 per night (USD)HomeAway
Sand Castle Luxurious Home Steps From Gulf Beaches heated pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful, decorated 1700 sf home with vaulted ceilings, luxurious furnishings and open plan entertaining. Accommodates ...
From $334 per night (USD)HomeAway
From $159 per night (USD)VRBO
**50 steps to the sand!**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** Accepting New Reservations!*** Newly renovated! This 2br/2bth unit is just 50 steps to white sandy beaches. The ...
From $159 per night (USD)VRBO
From $270 per night (USD)HomeAway
Beautiful Beach House situated right on the beach offering stunning views of the ocean
- Bedrooms:
- 2.5
- Bathrooms:
- 3
- Sleeps:
- 6
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $270 per night (USD)HomeAway
From $150 per night (USD)VRBO
Paradise Village - A 3 bedroom/2 bath pet friendly home with community pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Paradise Village! This 3 bedroom 2 bathroom pet friendly duplex is a short walk to the beautiful beaches on A ...
From $150 per night (USD)VRBO
From $200 per night (USD)HomeAway
Ivanhoe Lane Home: 3 BR/ 4 BA House on Holmes Beach, by RVA Sleeps 6
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Ivanhoe Lane in the popular island neighborhood of Key Royale where spacious homes sit on the pristine waters ...
From $200 per night (USD)HomeAway
From $150 per night (USD)VRBO
Anna Maria Island Beach Paradise 5-Heated Pool-Free Wi-Fi-Linen Service
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...
From $150 per night (USD)VRBO
From $330 per night (USD)HomeAway
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 $330 per night (USD)HomeAway
From $225 per night (USD)VRBO
Luxury Beachfront Resort- Heated Pool/Hot Tub - Direct Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Perfect for extended stays! Featuring 1 over-sized bedroom with an en-suite large bathroom with double vanities and sepa ...
From $225 per night (USD)VRBO
From $100 per night (USD)HomeAway
Gulfside 1Br/1Ba Apartment On Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Delightful private fully furnished one bedroom apartment on second floor of old Florida house located less than 100 feet ...
From $100 per night (USD)HomeAway
From $365 per night (USD)VRBO
Close to the Beach, Gulf Views! Private pool
- Bedrooms:
- 5.5
- Bathrooms:
- 7
- Sleeps:
- 14
View of the Gulf is located in Holmes Beach, directly across from the white sandy beaches of Anna Maria! Enjoy views of ...
From $365 per night (USD)VRBO
From $279 per night (USD)HomeAway
Gorgeous Home Just Steps to Beach, Miles of White Sandy Beach ST lic DWE5105216
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous home is just steps to the beach, with other beautiful homes nearby. This beautiful home is one of two, wit ...
From $279 per night (USD)HomeAway
From $140 per night (USD)VRBO
2 MIN WALK TO GULF BEACHES, LG HEATED POOL, XLG LANAI - BONUS ROOM & GAS GRILL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Whispering Palms Villa at North Beach Village is a bright and sunny, tastefully decorated beach style townhouse located ...
From $140 per night (USD)VRBO
From $240 per night (USD)HomeAway
TWO BEDROOM UNIT WITH POOL***GREAT LOCATION**STEPS TO THE BEACH!
- 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 queen sleeper sofa. Unit 20 ...
From $240 per night (USD)HomeAway
From $259 per night (USD)VRBO
Coastal Charm Meets Cottage Chic! Sparkling Pool/Spa *4 Doors To The Beach*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
TO ALLOW FOR PROPER CLEANING AND DISNFECTION OF PROPERTY BETWEEN STAYS EARLY CHECK-INS AND LATE CHECK-OUTS WILL BE UNAVA ...
From $259 per night (USD)VRBO
From $171 per night (USD)HomeAway
SeaStarVilla in Holmes Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Star Villa! This well constructed 3 bedroom and 3 bathroom Island home is ready to host up to six ...
From $171 per night (USD)HomeAway
From $150 per night (USD)VRBO
Beautiful 2 bedroom 2 bathroom Condo beach gear, private laundry free WIFI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Don't miss out on this newly renovated 2 bedroom 2 bathroom 2nd floor condo with elevator on the West side of Gulf drive ...
From $150 per night (USD)VRBO
From $80 per night (USD)HomeAway
Tropical Paradise On The Beach Permit VRC17-000168
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Video Tour link at the bottom. This cottage is located "on the beach" 3007 Avenue F on beautiful Holmes beach. It is th ...
From $80 per night (USD)HomeAway
From $150 per night (USD)VRBO
Anna Maria Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $150 per night (USD)VRBO
From $125 per night (USD)HomeAway
REDUCED RATES @ Siesta Sol Cottage! Sleeps 6-POOL-Short walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely, conveniently located ground level home in the heart of Holmes Beach. This two bedroom home has it all. Newly ins ...
From $125 per night (USD)HomeAway
From $172 per night (USD)VRBO
Minute walk to white sandy beaches & private Tiki Bar
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Mango Breeze is tucked away in the heart of Holmes Beach, located just 6 homes away from the Gulf beaches! Come getaway ...
From $172 per night (USD)VRBO
From $302 per night (USD)HomeAway
One house to the Beach with expansive heated pool!! Sleeps 8
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sunset Beach House just a few steps away from the Gulf beaches of Anna Maria Island. Sunset Beach is a 4 bed ...
From $302 per night (USD)HomeAway
From $79 per night (USD)VRBO
Moorings - pool view from this 2 bedroom/ 2 bath condo on Anna Maria Island!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a bright and well maintained two bedroom/ two bath condo in desirable Westbay Pointe & Moorings Condominiums sit ...
From $79 per night (USD)VRBO
From $119 per night (USD)HomeAway
Island Cottage with open living area, pool, ground floor very close to beach located in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half d ...
From $119 per night (USD)HomeAway
From $235 per night (USD)VRBO
Cozy Cabana West - Private Heated Pool - 4 Minute Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated in 2015, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. The villa is located in ...
From $235 per night (USD)VRBO
From $300 per night (USD)HomeAway
Private Heated Pool and Spa- Pet Friendly
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Buddy's Beach House. A beachy chic getaway just 2 blocks to the beach. Stroll to the beach with a beverage in ...
From $300 per night (USD)HomeAway
From $230 per night (USD)VRBO
Lake By The Beach Pool/Spa Home Overlooking Secluded Lake Native Landscaping
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is si ...
From $230 per night (USD)VRBO
From $79 per night (USD)HomeAway
Beach View 7 - a 2 Bed/ 2 Bath 2nd floor condo w/pool and close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Recently remodeled coastal cuteness! Summer of 2020 brought many updates to this lovely condo from the floors to the lin ...
From $79 per night (USD)HomeAway
From $232 per night (USD)VRBO
Windshore A! - 2 Minute Walk to Beach, Private Heated Pool, WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Built new in 2011, Windshore A leaves no wishes open when it comes to your vacation on Anna Maria Island. Within walking ...
From $232 per night (USD)VRBO
From $110 per night (USD)HomeAway
Sandy Pointe II Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a light and bright 2 bedroom/2 bath Condo that backs up to the lovely and serene mangroves (nature preserve). T ...
From $110 per night (USD)HomeAway
From $345 per night (USD)VRBO
EXCELLENT LOCATION IN THE HEART OF HOLMES BEACH ON ANNA MARIA ISLAND!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minutes walk to the oce ...
From $345 per night (USD)VRBO
From $119 per night (USD)HomeAway
Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Loggerhead Beach House just a few houses from the Gulf beaches on Anna Maria Island. Loggerhead Beach House i ...
From $119 per night (USD)HomeAway
From $379 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 $379 per night (USD)VRBO
From $136 per night (USD)HomeAway
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a gr ...
From $136 per night (USD)HomeAway
From $161 per night (USD)VRBO
Coral Breeze (B) 2BR / 2BA Duplex with private pool! Pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Breeze B (Units A and B ground level ranch style home) is your brand new paradise. Each 2 bedroom 2 bath side of t ...
From $161 per night (USD)VRBO
From $409 per night (USD)HomeAway
Mainsail Beach Inn 3 Bedroom Beach Front Unit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...
From $409 per night (USD)HomeAway
From $309 per night (USD)VRBO
Mainsail Beach Inn 2 Bedroom
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2 ba ...
From $309 per night (USD)VRBO
From $114 per night (USD)HomeAway
HOMES BEACH HACIENDA 2/1 Walking distance to the BEACH
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 99
This quaint island rental has a discounted price tag and it's only a block from the beach! Neat as a pin 2 bedroom, 1 ba ...
From $114 per night (USD)HomeAway
From $150 per night (USD)VRBO
62 STREET BEACHWALK HOME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A fabulous TOTALLY REMODELED AND DECORATED 3 Bedroom 2 Bath elevated single family home with vaulted ceilings, tile floo ...
From $150 per night (USD)VRBO
From $92 per night (USD)HomeAway
Gertie's East - a great 1/1, just steps to the beach. With Relaxing Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Gertie's Beach House East is a vibrant, well maintained and equipped island duplex. Just steps from the white sands and ...
From $92 per night (USD)HomeAway
From $163 per night (USD)VRBO
MYKONOS - A 3/2 heated pool home just steps to the beach. 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 $163 per night (USD)VRBO
From $339 per night (USD)HomeAway
3 Bedroom Townhouse - Your private Holmes Beach vacation home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The interior decor in your private Holmes Beach vacation rental is elegant, fresh and bright. These three bedroom, three ...
From $339 per night (USD)HomeAway
From $309 per night (USD)VRBO
Mainsail Beach Inn 2 Bedroom
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 ...
From $309 per night (USD)VRBO
From $125 per night (USD)HomeAway
Anna Maria Island Beach Paradise 10
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund ...
From $125 per night (USD)HomeAway
From $150 per night (USD)VRBO
Relax at this beachfront pet friendly home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
White Sands is in the perfect location! This charming beach cottage is located right on the beautiful Gulf of Mexico in ...
From $150 per night (USD)VRBO
From $350 per night (USD)HomeAway
Heated pool! Enjoy Gulf & Bay water views!
- Bedrooms:
- 5.5
- Bathrooms:
- 5
- Sleeps:
- 10
Caribbean Dream is a stunning, luxury home in Holmes Beach located just a short 3-minute walk to the Gulf beaches! This ...
From $350 per night (USD)HomeAway
From $180 per night (USD)VRBO
Tropical Paradise Cottage on the Beach VRC17-000167
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Video Tour Link at the bottom This cottage is located "on the beach" 3007 Avenue F, beautiful Holmes beach. It is th ...
From $180 per night (USD)VRBO
From $319 per night (USD)HomeAway
Lovely Island Home w/Pool, Sunset Views, Ping Pong, 5 Min Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sunsets on Carissa! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals 19 ...
From $319 per night (USD)HomeAway
From $125 per night (USD)VRBO
Gulf Beach Apartment - with Pool & Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Pristine,spacious1 bedroom apartment sleeps 4, only steps to the beautiful white sandy beach of Anna Marie Island. Fresh ...
From $125 per night (USD)VRBO
From $59 per night (USD)HomeAway
Castnetter Beach Resort 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $59 per night (USD)HomeAway
From $150 per night (USD)VRBO
Private pool and close to shops and restaurants! !! 🌴
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Calypso Cottage is a Mediterranean style home on Anna Maria Island, just a 5 minute stroll to the Gulf beaches! This ho ...
From $150 per night (USD)VRBO
From $170 per night (USD)HomeAway
Shell Game - 1683476
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Playa Encantada Beacfront Community just Steps to the Beach Shell Game has recently been transformed into a fun an ...
From $170 per night (USD)HomeAway
From $154 per night (USD)VRBO
Tranquil Anna Maria Island Resort, Unit 2... Only 4 units, all amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...
From $154 per night (USD)VRBO
From $85 per night (USD)HomeAway
200 Steps to the Beach- Families welcome- featured in Southern Living
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay with us if you like: * A place right on the beach with no busy streets to cross. * Your own private sun patio with ...
From $85 per night (USD)HomeAway
From $300 per night (USD)VRBO
Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Relax in this comfy, coastal home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach Hous ...
From $300 per night (USD)VRBO
From $350 per night (USD)HomeAway
30 Second Walk to the Gulf Beaches & the famous Beach Bistro!!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
With numerous views of the Gulf, the Gulfside Oasis is only a minute walk away from the sandy beaches and the famous Bea ...
From $350 per night (USD)HomeAway
From $259 per night (USD)VRBO
200' from Beach, Heated Pool and Spa, Upscale Furnishings, Elevator
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
Fantastic Location. 200 feet to the beach - a short one minute stroll - Gulf Views. Three story spacious luxury home. ...
From $259 per night (USD)VRBO
From $240 per night (USD)HomeAway
ONE BEDROOM UNIT WITH POOL/MARCH DATES AVAILABLE! STEPS TO BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a queen sleeper sofa. Unit 2 ...
From $240 per night (USD)HomeAway
From $209 per night (USD)VRBO
Family Beach home w/ Hot Tub, Fire Pit, Kayaks, Paddle Boards & LED 65" TV
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
95 five-star reviews says it all! Florida's best kept secret, Anna Maria Island, features beautiful white sugar sand be ...
From $209 per night (USD)VRBO
From $150 per night (USD)HomeAway
505 Waterfront Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront home with direct access to Bimini Bay. Custom pool deck, boat dock, outdoor shower and heated pool. Gourmet k ...
From $150 per night (USD)HomeAway
From $225 per night (USD)VRBO
Private heated beachfront home - pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Turtle Watch is a direct Gulf front, elevated home located in Holmes Beach! Enjoy Sunset views from the privacy of your ...
From $225 per night (USD)VRBO
From $230 per night (USD)HomeAway
High Speed WIFI, PRIVATE HEATED POOL AND SPA, BIKES - This house has it all
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...
From $230 per night (USD)HomeAway
From $130 per night (USD)VRBO
Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This complex at 7100 Gulf Drive is well managed, impeccably maintained and has a reputation of being one of the island's ...
From $130 per night (USD)VRBO
From $220 per night (USD)HomeAway
3 minute walk to the beach! Off the main road in a quiet and tropical setting,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
HEALTH & SAFETY OF GUESTS PURSUANT TO EXECUTIVE ORDER 20-123 AS ISSUED MAY 15, 2020 by the State of Florida and the M ...
From $220 per night (USD)HomeAway
From $199 per night (USD)VRBO
Beach Chic! Ensuite bathrooms with a yard.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our place is close to white sand beaches, the bay and city dock, parks, tennis courts, casual and fine dining, shopping, ...
From $199 per night (USD)VRBO
From $384 per night (USD)HomeAway
Private house and pool, close to beach, restaurants, shops on Anna Maria Island
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
SALTY DOGS IS A SINGLE FAMILY BEACH HOUSE. This is not a mirage, you get the entire house, it's just one property. Pri ...
From $384 per night (USD)HomeAway
From $409 per night (USD)VRBO
Water Front/Heated Pool/Dock/Walk To Beach/Self Check In-Out/High cleaning/WiFi.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama ...
From $409 per night (USD)VRBO
From $77 per night (USD)HomeAway
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 $77 per night (USD)HomeAway
From $164 per night (USD)HomeAway
RELAX or WORK by The Gulf Enjoy the Beach, Pools & Pickleball Specials Available
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy beautiful sunrises over the inner coastal while relaxing in our bright and open two bedroom condo, with all of the ...
From $164 per night (USD)HomeAway
From $150 per night (USD)VRBO
Directly Across the Street from Gulf Beaches! Last Minute December Savings!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Eyes on the Sunset is a gorgeous elevated home located directly across the street from the Gulf in Holmes Beach. This h ...
From $150 per night (USD)VRBO
From $225 per night (USD)HomeAway
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
ARECA COVE - A bright and wonderful 4 bedroom/ 3.5 bath home just a 3 minutes walk away from an astonishing white sand b ...
From $225 per night (USD)HomeAway
From $204 per night (USD)VRBO
Recently Remodeled 2 Bedroom Condo Across From Beach access St Lic CND5105119
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Very spacious two bedroom with a side den like area in the living room with a sleeper sofa for extra guest. Large flat p ...
From $204 per night (USD)VRBO
From $209 per night (USD)HomeAway
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 $209 per night (USD)HomeAway
From $254 per night (USD)VRBO
Beautiful Remodeled Condo Sandy Pointe Holmes Beach St lic CND5105157
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances ...
From $254 per night (USD)VRBO
From $171 per night (USD)HomeAway
Ebb Tide in Holmes Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3 bedroom/3 bath pool home is well a ...
From $171 per night (USD)HomeAway
From $169 per night (USD)VRBO
Visit Anna Maria Island! Relax at Heliconia House, enjoy your own heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NOTE: Please check current local/state Covid 19 restrictions before booking. In order to ensure your safety we have up ...
From $169 per night (USD)VRBO
From $95 per night (USD)HomeAway
Tropical Anna Maria Island Villa
- Bedrooms:
- 3.5
- 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 $95 per night (USD)HomeAway
From $355 per night (USD)VRBO
You Have Found Paradise-A premiere property on Anna Maria Island ***WATERFRONT
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
My Grand Floridian ***NEW--Party Pool Lights. Enhance your pool experience with lighting that creates an ambiance that ...
From $355 per night (USD)VRBO
From $200 per night (USD)HomeAway
Enjoy the Island Life on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Charming 2 bedroom 2 bath unit with all the comforts of home are included as well as access to the pool and tennis court ...
From $200 per night (USD)HomeAway
From $250 per night (USD)VRBO
Perfect summer getaway!! Escape to paradise; <2min walk to nation's best beach
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay is a gorgeous 4-bedroom/3.5 bathroom home within walking distance of the nation's most amazing white sand bea ...
From $250 per night (USD)VRBO
From $300 per night (USD)HomeAway
MAY $500 SPECIAL! Waterfront Island Escape w Guest House, Panoramic views!
- Bedrooms:
- 5.5
- Bathrooms:
- 5
- Sleeps:
- 10
Waterfront estate with breathtaking panoramic views of the bay. Wake up to sunrises over the water! This private island ...
From $300 per night (USD)HomeAway
From $150 per night (USD)VRBO
Tuscan-style Villa, close to it all! Pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This home's Mediterranean design sets the scene for a luxurious island getaway, Located on a quiet cul de sac in Holmes ...
From $150 per night (USD)VRBO
From $280 per night (USD)HomeAway
Crazy Cute Beach Cottage In Paradise
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fabulously styled cottage is set back 30 yards from the Gulf ocean (one house off the beach as the crow flies) ...
From $280 per night (USD)HomeAway
From $250 per night (USD)VRBO
Steps from the beach! Heated pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in the tropical splendor of this ultra-luxurious beachfront property on Anna Maria Island in a gated community tha ...
From $250 per night (USD)VRBO
From $59 per night (USD)HomeAway
BEACHFRONT condo, sleeps 6, updated, stocked with everything, popular location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently all remodeled and beautifully updated, this 2 bedroom 2 bath condo is located conveniently to restaurants and ...
From $59 per night (USD)HomeAway
From $329 per night (USD)VRBO
Close To The Beach And Restaurants With Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rent with #1193410 if you need 5 bedrooms! We treat for mosquitos from May through August 2 Bedrooms, 2 Bathrooms, an ...
From $329 per night (USD)VRBO
From $150 per night (USD)HomeAway
Ana Maria Villa East, Shared Heated Salt Pool, Steps to the Beach, Ground Level
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Palm Oasis Villa East is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $150 per night (USD)HomeAway
From $149 per night (USD)VRBO
CHARMING 2 Bed 2 Bath with PRIVATE HEATED Pool SPA Sleeps 6 FREE WiFi , WASHER/DRYER
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...
From $149 per night (USD)VRBO
From $450 per night (USD)HomeAway
Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our Island Retreat cottage, situated 3 blocks from the beach and 2 blocks from the bay with a heated pool and secluded y ...
From $450 per night (USD)HomeAway
From $154 per night (USD)VRBO
Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...
From $154 per night (USD)VRBO
From $349 per night (USD)HomeAway
6 Bed 6.5 Bath 2 minutes to beach **HEATED POOL & STAND ALONE HOT TUB** GARAGE BIKES Free Wifi
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...
From $349 per night (USD)HomeAway
From $309 per night (USD)VRBO
Anna Maria 2 Family Home w/ pool, beach/3 blocks.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Side B is being rented with private use of the pool and private use of all the fenced in area around the pool & unit. A ...
From $309 per night (USD)VRBO
From $369 per night (USD)HomeAway
PRIVATE POOL, WALK TO BEACH
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful ground level split duplex offers three bedrooms (two king rooms and one twin room with two twin beds) and ...
From $369 per night (USD)HomeAway
From $449 per night (USD)VRBO
6 BED 5.5 BATH Heated Pool/Spa WATER SLIDE Minute to the Beach! Roof top deck Free WiFi SLEEPS 12
- Bedrooms:
- 6.5
- Bathrooms:
- 6
- Sleeps:
- 12
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...
From $449 per night (USD)VRBO
From $125 per night (USD)HomeAway
AMI is a paradise destination! Join us for some Fun in the sun 🌞!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our single story beach house is recently redecorated and includes a large, brand new heated pool. The home is located in ...
From $125 per night (USD)HomeAway
From $239 per night (USD)VRBO
newly remodel North Gulf Villa few steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Find everything that makes a fun beach getaway on Anna Maria Island memorable when you stay at North Gulf Villa Beach v ...
From $239 per night (USD)VRBO
From $375 per night (USD)HomeAway
Beach Charm Guest Cottage—Ground level—Private, Tropical & Quiet!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
'Feel the Charm of an Old-Style Florida Beach' at Beach Charm!! Our 1 bedroom/1 bathroom private entry guest cottage is ...
From $375 per night (USD)HomeAway
From $240 per night (USD)VRBO
Relax and Tan on Your Private Patio... Just a minute to the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this boutique-styled cottage and the white sandy beaches that make Anna Maria Island so famous. The Cottage is ...
From $240 per night (USD)VRBO
From $494 per night (USD)HomeAway
Fins Up! New Home w/Private Heated Pool & 4 Min Walk to Beach w/Beach Gear!
- Bedrooms:
- 4.5
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fins Up! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals 1250 sq. ft. ...
From $494 per night (USD)HomeAway
From $173 per night (USD)VRBO
Best Little Beach House on Anna Maria Island...With a pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Check in / Check out - SATURDAYS ONLY* This is the Best Little Beach House on Anna Maria Island...with a pool. Our h ...
From $173 per night (USD)VRBO
From $200 per night (USD)HomeAway
Anna Maria Island Townhouse - Simply Beautiful!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This townhouse is beautifully decorated and completely modern with everything you need for the perfect vacation in parad ...
From $200 per night (USD)HomeAway
From $179 per night (USD)VRBO
Coconut Breeze in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coconut Breeze is a beautifully renovated duplex only a short 5 minute walk to the beach. Coconut Breeze is finished in ...
From $179 per night (USD)VRBO
From $130 per night (USD)HomeAway
★ Spacious Condo ★ 2 Patios |Steps to Beach| 2BD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Very private! Spacious 2 bedroom 2 full bath condo is just steps to the beach. Ocean view from your unit with two screen ...
From $130 per night (USD)HomeAway
From $131 per night (USD)VRBO
Beach Front Condo with stunning Sunset Views! ☼
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Shores 106 is a Gulf front condo located in Holmes Beach on Anna Maria Island. Enjoy beautiful spectacular sunset v ...
From $131 per night (USD)VRBO
From $179 per night (USD)HomeAway
Sunkissed in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunkissed is a beautiful elevated townhome that is located in Holmes Beach-just a short stroll to the gorgeous white san ...
From $179 per night (USD)HomeAway
From $154 per night (USD)VRBO
Tranquil Anna Maria Island Resort, Unit 3... Only 4 units, all amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...
From $154 per night (USD)VRBO
From $309 per night (USD)HomeAway
Direct Beachfront 2 BD Condo On Florida’s Beautiful Gulf Coast!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Florida Vacation Dream Spot - easy and fun! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up a ...
From $309 per night (USD)HomeAway
From $179 per night (USD)VRBO
Panoramic rooftop view, view from unit, 1 minute walk to beach, heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
NOTICE: We are a 7 night minimum stay rental property, and licensed by the state of Florida. WE ARE OPEN per CDC and F ...
From $179 per night (USD)VRBO
From $410 per night (USD)HomeAway
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 $410 per night (USD)HomeAway
From $174 per night (USD)VRBO
Tranquil Anna Maria Island Resort, Unit 4... Only 4 units, all amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just 300 steps from the beach, Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one tw ...
From $174 per night (USD)VRBO
From $186 per night (USD)HomeAway
Salty Turtle in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Salty Turtle! Bask in the tropical charm of this three-bedroom Holmes Beach bungalow, a darling Anna Maria Is ...
From $186 per night (USD)HomeAway
From $185 per night (USD)VRBO
Charming 3 bedroom cottage - bikes & beach gear!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Key Largo Cottage is an adorable bungalow style single family home on a quiet street with an over-sized pool, bikes, bea ...
From $185 per night (USD)VRBO
From $175 per night (USD)HomeAway
Reduced rates - 25% off! Private pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Hideaway is a cute as a button, ground level home that features a tropical oasis for a backyard in Holmes Beach. ...
From $175 per night (USD)HomeAway
From $250 per night (USD)VRBO
North end, large outdoor pool area perfect for Family Fun!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Pineapple is a gorgeous newly renovated 4 bedroom and 4 bathroom home that features a stunning backyard oasis per ...
From $250 per night (USD)VRBO
From $275 per night (USD)HomeAway
Waters Edge 110N in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Waters Edge, a beachfront getaway with stunning views! The Waters Edge #110N condo is a beautiful two b ...
From $275 per night (USD)HomeAway
From $184 per night (USD)VRBO
Literally steps to the beach! Spacious and Light!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Up 12 steps from your front door is a lovely Gulf and beach view. Just 75 steps to the beach, no roads to cross! Fabul ...
From $184 per night (USD)VRBO
From $285 per night (USD)HomeAway
Luxury-2 Master King Suites, Private Htd Pool, Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
I love speaking with my guests. Please don't hesitate to call or write me, Lauren, the owner. Please feel free to loo ...
From $285 per night (USD)HomeAway
From $100 per night (USD)VRBO
Beachfront - Can't get much closer to paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Breeze is a single-family home located right on the Gulf Beaches! This home includes the following features: • ...
From $100 per night (USD)VRBO
From $338 per night (USD)HomeAway
Luxury 3 Bed, 3 En Suite Baths, Private Htd Pool, 0 Blocks to Beach - Just Steps
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
I love speaking with my guests. Please don't hesitate to call or write me, Lauren, the owner. Please feel free to loo ...
From $338 per night (USD)HomeAway
From $230 per night (USD)VRBO
Weekly Summer booking available 4 Bedroom 3 Bathroom , bikes, beach gear, pool and spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaura ...
From $230 per night (USD)VRBO
From $186 per night (USD)HomeAway
Coral Beach in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Coral Beach! This beautiful 3 bedroom, 2 bathroom pool home comfortably accommodates 6 guests. From the ...
From $186 per night (USD)HomeAway
From $200 per night (USD)VRBO
Beach ☼ Front Condo with Sunset Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Paradise 1 has the best sunset views in Holmes Beach, from the privacy of your own home! This home includes the ...
From $200 per night (USD)VRBO
From $429 per night (USD)HomeAway
Beachfront Cottage -Ground Floor, Family Friendly! Great location. Free wi-fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You won't want to leave our cute and cozy gulf front cottage, which we've named 'Can't Wait'.... We are 'right on th ...
From $429 per night (USD)HomeAway
From $279 per night (USD)VRBO
Happy Island Cottage with heated Pool + UV AIR Filtration System! (2020)
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
A 2000 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the bea ...
From $279 per night (USD)VRBO
From $300 per night (USD)HomeAway
TRUE BEACHFRONT HOME DIRECTLY ON SUGAR WHITE SANDS WITH HEATED POOL - IDYLLIC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CLEANLINESS HAS ALWAYS BEEN A TOP PRIORITY. WE WANT YOU TO KNOW THAT WE ARE DOING OUR PART TO HELP OUR GUESTS STAY SAFE ...
From $300 per night (USD)HomeAway
From $200 per night (USD)VRBO
Manatee Watch - Waterfront! Hot Tub! 3 Min Walk To Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
MANATEE WATCH - A marvelous waterfront 3 bedroom/ 2 bath home just a short walk away from an astonishing white sand beac ...
From $200 per night (USD)VRBO
From $36 per night (USD)HomeAway
3 King bedroom and Bunk room for 4 private pool, bikes & beach gear
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful open concept home. 3 king bedrooms with ensuites and a den with 2 single bunk beds makes this property perfec ...
From $36 per night (USD)HomeAway
From $179 per night (USD)VRBO
Sapphire Beach House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casual yet luxurious, this three-bedroom duplex with a private, heated pool and close proximity to the beach is the perf ...
From $179 per night (USD)VRBO
From $59 per night (USD)HomeAway
Castnetter Beach Resort 5
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $59 per night (USD)HomeAway
From $359 per night (USD)VRBO
Close to the Beach and Restaurants with a heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We treat for mosquitos from May through August Island Vibe is a renovated three bedroom, two bath home with a private h ...
From $359 per night (USD)VRBO