Holmes Beach Rentals
From $95 per night (USD)HomeAway
Beach View of Manatee #1: 2 BR/ 2 BA Condo on Holmes Beach by RVA, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for that tropical island getaway? Look no further than Beach View of Manatee #1 by RVA. This lovely, light and b ...
From $95 per night (USD)HomeAway
From $138 per night (USD)VRBO
Marbella - GULF FRONT CONDO WITH BEAUTIFUL VIEW - Sleeps 4!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Marbella! This gorgeous vacation villa is located on the top floor of a beach front condo complex. Enjoy the ...
From $138 per night (USD)VRBO
From $123 per night (USD)HomeAway
New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
- Bedrooms:
- 3
- 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 $123 per night (USD)HomeAway
From $120 per night (USD)VRBO
A lovely 2 bed and 2 bath property just moments from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $120 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 $369 per night (USD)VRBO
Mainsail Beach Inn 2 Bedroom Beach Front Unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The furnishings and appointments in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bed ...
From $369 per night (USD)VRBO
From $184 per night (USD)HomeAway
Anna Maria Island Waterfront house with private boat dock, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning single level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently r ...
From $184 per night (USD)HomeAway
From $225 per night (USD)VRBO
Coastal Cottage On Holmes Beach With Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Coastal cottage located 1 block from fabulous white sands of holmes beach. Stay in comfort in our spacious 3 bedroom 2 b ...
From $225 per night (USD)VRBO
From $150 per night (USD)HomeAway
Sunrise Serenity - Spacious 3/2.5 town home with community heated pool
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
For your relaxing and family fun, Anna Maria Island vacation, check out this spacious beautiful 3 bedroom, 2.5 bath town ...
From $150 per night (USD)HomeAway
From $409 per night (USD)VRBO
Mainsail Beach Inn 3 Bedroom Beach Facing 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)VRBO
From $298 per night (USD)HomeAway
Beautiful Island Home-Great Amenities- Pool- Grill- Close to the Gulf Beaches!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coconut Hideaway located just one house away from the Gulf beaches of Anna Maria Island. This beach house has ...
From $298 per night (USD)HomeAway
From $160 per night (USD)VRBO
Our Little Secret - Canal Front Pool Home - Close to the Beaches
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
Location, Location (see map): There are seven miles of pristine, quartz sand beaches shimmering along our island and you ...
From $160 per night (USD)VRBO
From $184 per night (USD)HomeAway
Beautiful 2 bedroom 2nd level across the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We highly recommend TRIP INSURANCE Updated 2 bedroom 2 bathroom , with new kitchen and all furniture. Perfect for 2 coup ...
From $184 per night (USD)HomeAway
From $161 per night (USD)VRBO
Coral Breeze (A) Perfect 2 bedroom/2 bathroom with private pool! Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Breeze (Units A and B) is your brand new paradise. Each 2 bedroom 2 bath side of this adorable duplex features eve ...
From $161 per night (USD)VRBO
From $189 per night (USD)HomeAway
Sunbreeze - charming 3/2.5 home, great pool, steps to the beach!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
This stunning tropical oasis Sunbreeze features hardwood and tile floors throughout the home, front and back decks to un ...
From $189 per night (USD)HomeAway
From $103 per night (USD)VRBO
Beach Dream A - Beach life at its best
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
Beach Dream A is a cozy classic Florida style downstairs unit of a duplex just a few houses away from the sandy beaches ...
From $103 per night (USD)VRBO
From $300 per night (USD)HomeAway
Luxury Four Bedroom Home with Easy Access to Beach. Pool and private Patio.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Aqua Oasis located just one house away from the Gulf beaches of Anna Maria Island. This beach house has a pri ...
From $300 per night (USD)HomeAway
From $135 per night (USD)VRBO
Comfortable and spacious property with raised deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $135 per night (USD)VRBO
From $309 per night (USD)HomeAway
Our Waterfront Home Is All Ready Just For You!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a v ...
From $309 per night (USD)HomeAway
From $193 per night (USD)VRBO
Isle Haven A - steps to the beach and many other conveniences - pet friendly!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
Isle Haven A is the perfect home for you to make memories that will last a life time! It is the perfect beach getaway to ...
From $193 per night (USD)VRBO
From $110 per night (USD)HomeAway
Quiet Nights of Quiet Stars on Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Quiet nights of quiet stars, quiet walks by quiet sea, quiet thoughts on quiet street, oh how lovely. A recent guest ha ...
From $110 per night (USD)HomeAway
From $659 per night (USD)VRBO
Luxury 4BR, 3 1/2 BA House with Heated Pool, 4 houses from the beach
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Approximately 500 FEET FROM THE GORGEOUS BEACHES of Anna Maria Island on the Gulf of Mexico, you will be able to head do ...
From $659 per night (USD)VRBO
From $529 per night (USD)HomeAway
PARADISAICAL ENCLAVE WATER FRONT 5* POOL -FISHING DOCK -KAYAK -BIKES-FAMILY FUN
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
DUE TO AVAILABILITY RESTRICTIONS A MINIMUM STAY REQUIREMENT MAY BE IMPOSED. PLEASE CONTACT OWNER IF CONFLICTS OCCUR WHI ...
From $529 per night (USD)HomeAway
From $339 per night (USD)VRBO
Mainsail Beach Inn 3 Bedroom Townhouse
- 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)VRBO
From $500 per night (USD)HomeAway
Gulf Front Home On Shady Lot. Open Doors And Step Into The Gulf Of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 BR / 2 bath private home located directly on the Gulf. Outdoor grill, covered porch and dining as you overlook gorgeo ...
From $500 per night (USD)HomeAway
From $193 per night (USD)VRBO
It's my Dream - private heated pool, 2 minute walk to the beach! Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It's My Dream is a brand new and lovely island-themed private duplex with 3 bedrooms and 2 bathrooms. Equipped with a pr ...
From $193 per night (USD)VRBO
From $125 per night (USD)HomeAway
Anna Maria - Steps From The Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect place to put your feet up and relax. One of four units in the condo gives your getaway a private feeling where y ...
From $125 per night (USD)HomeAway
From $169 per night (USD)VRBO
Castnetter Beach Resort 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anna Maria Island's "Castnetter 6" is a delightful Island local located directly across the street from the seven acre " ...
From $169 per night (USD)VRBO
From $119 per night (USD)HomeAway
Holmes Beach Cottage Steps to the Beach with Private Heated Pool!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack i ...
From $119 per night (USD)HomeAway
From $105 per night (USD)VRBO
Gulf Winds - a completely remodeled cozy cottage - pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The cozy front porch of Gulf Winds invites you to have your morning coffee or your evening cocktail and in the back yard ...
From $105 per night (USD)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
From $200 per night (USD)VRBO
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)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
From $174 per night (USD)VRBO
Three Bedroom Ground Floor Home with Retro Finishes and many Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Lime Cottage located just 2 blocks from the Gulf beaches of Anna Maria Island. Lime Cottage is a ground level ...
From $174 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 $270 per night (USD)VRBO
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)VRBO
From $120 per night (USD)HomeAway
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)HomeAway
From $334 per night (USD)VRBO
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)VRBO
From $159 per night (USD)HomeAway
**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)HomeAway
From $100 per night (USD)VRBO
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)VRBO
From $335 per night (USD)HomeAway
Unique Lighthouse by AMIBeachClub
- 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)HomeAway
From $335 per night (USD)VRBO
Elegant Southern 4 bed pool home last minute cancellation available now!
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4 bedroom two storey Southern style home with a pool at 402 Clark Lane in Holmes Beach, Anna Maria Island. The ...
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 $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 $100 per night (USD)VRBO
Luxury apartment with a view of the lagoon by the Gulf of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kesästä 2019 lähtien täydelliset uudet laitteet, joissa on hurrikaaniturvalliset ikkunat ja terassit, sekä hurrikaanitur ...
From $100 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 $143 per night (USD)VRBO
3011 Ave E-2 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3011 Ave E-2 Triplex Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC16-000051 Pet friendly. ...
From $143 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 $171 per night (USD)VRBO
Island Beach Club 3 in Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 3 - Condo 2 Bedroom / 1 Bath ground level gulf front , maximum occupancy of 4 people. Community ...
From $171 per night (USD)VRBO
From $150 per night (USD)HomeAway
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)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 $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 $136 per night (USD)VRBO
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)VRBO
From $114 per night (USD)HomeAway
HOMES BEACH HACIENDA 2/1 Walking distance to the BEACH
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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 $75 per night (USD)VRBO
Two Bed One Bath Beach Side Rental on Anna Maria Island steps to Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Location, location, location, this cozy quaint beach house is centrally located on Anna Maria Island and is less than a ...
From $75 per night (USD)VRBO
From $345 per night (USD)HomeAway
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)HomeAway
From $119 per night (USD)VRBO
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)VRBO
From $379 per night (USD)HomeAway
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)HomeAway
From $110 per night (USD)VRBO
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)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 $79 per night (USD)HomeAway
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)HomeAway
From $310 per night (USD)VRBO
Elegant Beach House with Private Pool, Minutes From The Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your piece of paradise on Anna Maria Island! Spacious floor plan with 2 bedrooms and living area downstairs, ...
From $310 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 $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 $409 per night (USD)VRBO
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)VRBO
From $309 per night (USD)HomeAway
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)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 $163 per night (USD)HomeAway
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)HomeAway
From $209 per night (USD)VRBO
Relax in This Lovely Waterfront Home with Heated Pool and Boat Dock & Lift
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful ground level waterfront home gives you the best that island living has to offer. Situated in tranquil Ho ...
From $209 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 $160 per night (USD)HomeAway
Luxury Anna Maria Island Home w/Private Pool, Waterfall; 3 Bedrooms/3 Full Baths
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Chez Shell is a Mediterranean-style beach home that offers a luxurious getaway. The highlight of this renovated a ...
From $160 per night (USD)HomeAway
From $125 per night (USD)VRBO
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)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 $125 per night (USD)VRBO
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)VRBO
From $129 per night (USD)HomeAway
Martinique 505 South
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Must be booked 30 days in advance. VRC#20-000110 Martinique 505 South - Condo 2 Bedroom / 2 Bath gulf view ...
From $129 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 $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 $129 per night (USD)HomeAway
Fountain Head 8 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fountain Head 8 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. VRC16-000062 Community pool. ...
From $129 per night (USD)HomeAway
From $639 per night (USD)VRBO
Skip to Beach & Shops in New Stunning Home, Pool/Spa, Beach Gear, Dogs OK
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to She's Always Right! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals Th ...
From $639 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 $157 per night (USD)VRBO
313 Island Walk in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Walk 313 - Townhouse 3 Bedroom/ 2 .5 Bath with private pool , maximum occupancy of 6 people. VRC16-000052 ...
From $157 per night (USD)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
From $170 per night (USD)VRBO
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)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 $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, & one two- ...
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 $204 per night (USD)HomeAway
Sunplaza 115 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun Plaza West 115 - Condo 2 Bedroom/ 2 Bath gulf front , maximum occupancy of 4 people. VRC16-000083 Commun ...
From $204 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
APRIL open! Beach home w/ Hot Tub, Fire Pit, Kayaks, Paddle Boards & LED 65" TV
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
85 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 $118 per night (USD)HomeAway
266 S Harbor in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
266 S. Harbor - Private home 3 Bedroom/ 2 Bath , maximum occupancy of 6 people. Distance to the Beach: 3 blocks ...
From $118 per night (USD)HomeAway
From $225 per night (USD)VRBO
Ground Floor Luxury Home, Heated Pool and Spa STEPS TO BEACH!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 10
After a sunny day at the beach, use the outdoor foot shower to cool down and rinse your sandy feet. Take a dip into the ...
From $225 per night (USD)VRBO
From $136 per night (USD)HomeAway
3011 Ave E-3 in Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
3011 Ave E-3 - Triplex Condo 1 Bedroom/ 1 Bath , maximum occupancy of 4 people. VRC16-000051 Pet friendly. ...
From $136 per night (USD)HomeAway
From $230 per night (USD)VRBO
High Speed WIFI, PRIVATE HEATED POOL AND SPA, BIKES - This house has it all
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 3.5 bathroom. This home is ideally located just down the street from the white sand beaches, restaurants and s ...
From $230 per night (USD)VRBO
From $130 per night (USD)HomeAway
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)HomeAway
From $129 per night (USD)VRBO
Fountain Head 6 in Holmes Beach
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
Fountain Head 6 - Condo 2 Bedroom / 1.5 Bath , maximum occupancy of 4 people. VRC16-000061 Community pool. ...
From $129 per night (USD)VRBO
From $114 per night (USD)HomeAway
Sandy Point 111 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sandy Point 111 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Distance to the Beach: 4 blocks VR ...
From $114 per night (USD)HomeAway
From $114 per night (USD)VRBO
Surf Rider's Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Surf Rider's Cottage! NOW with PRIVATE POOL! West of Gulf Drive, this cute Island bungalow is just perf ...
From $114 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 $649 per night (USD)HomeAway
Big Luxury 6 bd/pool/spa! Bikes! Kayak! Reviews! Beach! 3/6-3/12 open!
- Bedrooms:
- 6.5
- Bathrooms:
- 6
- Sleeps:
- 12
Come enjoy a large family and friends gathering at this spacious brand new luxury home just a few minutes stroll to the ...
From $649 per night (USD)HomeAway
From $209 per night (USD)VRBO
Private paradise w/ all the toys & golf cart!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The health and safety of our guests and employees is our number one priority. Please know that after each stay, our home ...
From $209 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 $130 per night (USD)VRBO
Anna Maria Island “A Turtle's Nest” 1 block to the beach Private Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Creative booking options available. Message for details. New to VRBO in 2017 this 3 bedroom 2 bathroom home is 1 bl ...
From $130 per night (USD)VRBO
From $129 per night (USD)HomeAway
Gulf View Townhouses 3
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf View Townhouse 3 - Condo 2 Bedroom / 2 1/2 Bath , maximum occupancy of 4 people. VRC16-000063 Community ...
From $129 per night (USD)HomeAway
From $300 per night (USD)VRBO
TOES IN THE SAND! GULF FRONT HOME WITH HEATED POOL, GORGEOUS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Last minute cancellation - discounted rate for the 21st January - 4th February. CLEANLINESS HAS ALWAYS BEEN A TOP PRIOR ...
From $300 per night (USD)VRBO
From $384 per night (USD)HomeAway
Private House, pool and spa. Close to Holmes Beach restaurants, shops & marina.
- 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 $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 $114 per night (USD)HomeAway
Sandy Point Cove 112
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Point Cove 112 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. ...
From $114 per night (USD)HomeAway
From $150 per night (USD)VRBO
RELAX and enjoy this tranquil 2 bedroom condo on Holmes Beach/Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your island oasis awaits! Welcome to your 2-bedroom, 2-bathroom ground floor condo with added community benefits in Holm ...
From $150 per night (USD)VRBO
From $150 per night (USD)HomeAway
Pet friendly Tuscan styled Villa, close to it all
- 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)HomeAway
From $275 per night (USD)VRBO
White Sands Beach House - Luxury home, heated pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly redecorated in April 2017, this beachy, four-bedroom, three-bath vacation rental is located in the middle of Anna ...
From $275 per night (USD)VRBO
From $170 per night (USD)HomeAway
Beach Front King Room - Heated Pool/Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Overview Anna Maria Beach Resort Unit 1 King Bed - Sleeps 4 total Gorgeous Resort Views Luxury Resort Pool and Hot Tub C ...
From $170 per night (USD)HomeAway
From $280 per night (USD)VRBO
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)VRBO
From $250 per night (USD)HomeAway
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)HomeAway
From $699 per night (USD)VRBO
3 Houses to Beach Large Lux Home, Pool/Spa, Gulf View, Outdoor Bar/Tiki, Pets OK
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Beachy Villa Vista! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals 21 ...
From $699 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
*** January through April, there is a two-week minimum rental. For rental periods for one month or longer, there is a 25 ...
From $59 per night (USD)HomeAway
From $25 per night (USD)VRBO
Close walk to the beach! Private Pool/Spa
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hidden Treasure is a beautiful 4 bedroom and 2 bathroom single family home tucked away on Anna Maria Island with just a ...
From $25 per night (USD)VRBO
From $329 per night (USD)HomeAway
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)HomeAway
From $300 per night (USD)VRBO
Summer Booking 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)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 $171 per night (USD)VRBO
Island Beach Club 21
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 21 - Condo 2 Bedroom / 2 Bath gulf front , maximum occupancy of 4 people. Community pool. ...
From $171 per night (USD)VRBO
From $149 per night (USD)HomeAway
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)HomeAway
From $853 per night (USD)VRBO
Gorgeous 6 Bed Home w/ Pool, Spa, Rooftop Gulf View, Block to Beach
- Bedrooms:
- 8.5
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Breaking Waves! On Anna Maria Island (Holmes Beach, FL) Managed by Once Upon A Beach Vacation Rentals Highl ...
From $853 per night (USD)VRBO
From $100 per night (USD)HomeAway
Sandy Point 109 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Point 109 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. V ...
From $100 per night (USD)HomeAway
From $225 per night (USD)VRBO
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)VRBO
From $204 per night (USD)HomeAway
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)HomeAway
From $95 per night (USD)VRBO
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)VRBO
From $196 per night (USD)HomeAway
Blocks to the white sand beaches with a backyard oasis that you will never want to leave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
BOOK WITH CONFIDENCE ALL RESERVATIONS MADE AFTER FEBRUARY 18TH 2021, WILL BE REFUNDED 85% OF THE TOTAL BOOKING COST IF C ...
From $196 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 $171 per night (USD)HomeAway
Island Beach Club 24
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. Community pool. ...
From $171 per night (USD)HomeAway
From $329 per night (USD)VRBO
One Block to Beach! 2 beds / 2 Bath - West of Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"Old Florida" elevated beach cottage just one block from the best beaches on Anna Maria Island! Located on the West sid ...
From $329 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 $280 per night (USD)HomeAway
🌴🌴🌴🌴🌴 BEAUTIFUL HEATED POOL GROUND FLOOR SINGLE FAMILY HOME!
- Bedrooms:
- 6.5
- Bathrooms:
- 6
- Sleeps:
- 14
Ground Level Luxury Villa in Prime Location! VERY CLOSE TO BEACH!!! Luxurious ground level home located at 124 50th Stre ...
From $280 per night (USD)HomeAway
From $171 per night (USD)VRBO
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)VRBO
From $169 per night (USD)HomeAway
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)HomeAway
From $250 per night (USD)VRBO
One Block to Beach! 2 bed / 2 bath - West of Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
"Old Florida" elevated beach cottage just one block from the best beaches on Anna Maria Island! Located on the West sid ...
From $250 per night (USD)VRBO
From $164 per night (USD)HomeAway
Relax By The Gulf In Our Beautiful Condo Check for Last Minute Specials
- 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 $450 per night (USD)VRBO
Anthony Beach Cottages - Island Retreat in Holmes Beach with 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)VRBO
From $154 per night (USD)HomeAway
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, & one two- ...
From $154 per night (USD)HomeAway
From $225 per night (USD)VRBO
Walk to the beach right from your balcony!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy amazing views of the Gulf of Mexico from the privacy of your own balcony at The Reefs Edge condo in Sunset Cove! ...
From $225 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:
- 14
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 $175 per night (USD)HomeAway
AMI Beautiful Home, Sparkling Clean, Easy Walk to Beach & Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Custom built this three bedroom, two bath home is beautifully designed for six guests. Come to Island Breeze and relax w ...
From $175 per night (USD)HomeAway
From $369 per night (USD)VRBO
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)VRBO
From $449 per night (USD)HomeAway
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)HomeAway
From $440 per night (USD)VRBO
1 Block to Beach, LARGE Private Pool - 6 Bdrm Luxury House!
- Bedrooms:
- 6.5
- Bathrooms:
- 6
- Sleeps:
- 10
Holmes Beach House For Rent - Luxury Vacation Rental on Anna Maria Island, Florida Shore House is a newer built luxury ...
From $440 per night (USD)VRBO