Holmes Beach Rentals
From $849 per night (USD)VRBO
La Casa Costiera Blue Water - Newly Renovated, Top Floor Beachfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NOTE: Pool and hot tub will not be available from September 8th to September 28th, 2025. AT A GLANCE: - La Casa Costie ...
From $849 per night (USD)VRBO
From $416 per night (USD)VRBO
Waterfront Paradise In The Exclusive Neighborhood Of Key Royale
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
IMPORTANT: If calendar shows dates being available, but no quote is generated, please send us a message by selecting the ...
From $416 per night (USD)VRBO
From $246 per night (USD)VRBO
Bird of Paradise by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Bird of Paradise is a tr ...
From $246 per night (USD)VRBO
From $286 per night (USD)Expedia
Palm Villa by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Palm Villa at Island Garden Villas, where Old Florida charm meets refreshing modern luxury. *Features includ ...
From $286 per night (USD)Expedia
From $302 per night (USD)VRBO
Island Vibe 3: Close to Beach with Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Island Vibe 3! This is a renovated 2-bedroom, 2-bathroom home with private, heated and cooled pool, tropical ...
From $302 per night (USD)VRBO
From $339 per night (USD)Expedia
Summer Special! Beautiful home, moments from the beach with beach gear and Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We call this Home Beach Beauty for good reason! This beautiful home is West of Gulf Drive and only 175 steps to the beac ...
From $339 per night (USD)Expedia
From $373 per night (USD)VRBO
Sunny 3BR/3BA Home. 8 Houses from Beach. Two Master Suites.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Private single family home on a quiet side street, 8 houses from the beautiful world-class beaches of Anna Maria Island. ...
From $373 per night (USD)VRBO
From $268 per night (USD)VRBO
Two bedroom1 bath unit with pool Steps to the beach. Great location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a futon sleeper sofa. Unit 20 ...
From $268 per night (USD)VRBO
From $1093 per night (USD)VRBO
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide,,NO STORM DAMAGE! -1 Min Beach Wlk
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Featuring 6 bedrooms (sleeps 14), 5.5 baths and a fantastic location...NO STORM DAMAGE!!! - just a 1 minute walk to the ...
From $1093 per night (USD)VRBO
From $642 per night (USD)Expedia
Paradise Found managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
401 42nd Street Holmes Beach, FL 34217 VRC17-000010 Book with confidence: You may cancel your reservation up to 60 days ...
From $642 per night (USD)Expedia
From $194 per night (USD)VRBO
Anna Maria by the Bay (30 day minimum)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully furnished bayside condo with gorgeous relaxing view. End unit, many windows let the sights in from every an ...
From $194 per night (USD)VRBO
From $687 per night (USD)Expedia
Angel Sea managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
🌴 Angel Sea by Beach Retreats Vacation Rentals VRC19-000188 📍 4118 5th Ave, Holmes Beach, FL 34217 🏡 6 Bedrooms | 3.5 ...
From $687 per night (USD)Expedia
From $253 per night (USD)VRBO
Island Townhouse - 200 Steps to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic 2 bedroom / 2 bath town home just 200 steps to the Beach. Sleeps 4. This is the end unit closest to the beac ...
From $253 per night (USD)VRBO
From $356 per night (USD)VRBO
1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect summer or winter hideaway!!! Located on Quiet Avenue E not busy Gulf Drive. Completely renovated one bedroom, o ...
From $356 per night (USD)VRBO
From $183 per night (USD)VRBO
Charming! 1.5 blocks to Beach! Quiet & Convenient.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Adorable cottage-style duplex only 1.5 blocks to beautiful Gulf of Mexico beach in Holmes Beach. 3min. walk to beach ...
From $183 per night (USD)VRBO
From $701 per night (USD)Expedia
Paradise Beach House managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
403 42nd Street, Holmes Beach FL 34217 VRC19-000276 Book with confidence: NO CANCELATION FEES Cancellation Policy (Eff ...
From $701 per night (USD)Expedia
From $384 per night (USD)VRBO
A Shore Thing by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A Shore Thing is a beautifully renovated key west style 3 bedroom beach house. Plenty of room for the whole family and f ...
From $384 per night (USD)VRBO
From $614 per night (USD)Expedia
Emerald Bay managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
🌊 Emerald Bay 📍 306A Clark Street, Holmes Beach, FL 34217 📌 VRC17-000006 | 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | He ...
From $614 per night (USD)Expedia
From $921 per night (USD)VRBO
Surf Side Beach House GULF VIEWS hosted by Beach Retreats Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Vie ...
From $921 per night (USD)VRBO
From $611 per night (USD)Expedia
AMI Villa by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Paradise - AMI Villa! Make this charming 3 bedroom, 3 bath Mediterranean beach villa your home away from home ...
From $611 per night (USD)Expedia
From $488 per night (USD)VRBO
Crosswind Cottage managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Crosswind Cottage 📍 312 A 61st Street, Holmes Beach, FL 34217 📌 VRC19-000277 | 3 Bedrooms | 2.5 Bathrooms | Sleeps ...
From $488 per night (USD)VRBO
From $540 per night (USD)Expedia
Turtle's Bay managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
306 Clark drive (B) Holmes Beach, FL 34217 VRC17-000009 Dog Friendly! Beautiful open concept home. 3 king bedrooms with ...
From $540 per night (USD)Expedia
From $436 per night (USD)VRBO
Salt Air East managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC19-000278 Book with confidence: NO CANCELATION FEES Cancellation Policy (Effective for reservations made on or afte ...
From $436 per night (USD)VRBO
From $1042 per night (USD)Expedia
Oasis by the Beach managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
202 69 th Street - Holmes Beach - FL 34217 VRC17-000120 Book with confidence: NO CANCELATION FEES Cancellation Policy ...
From $1042 per night (USD)Expedia
From $511 per night (USD)VRBO
Seahorse Beach House managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
202 81 st Street - Holmes Beach - Fl 34217 VRC17-000118 Book with confidence: NO CANCELATION FEES Cancellation Policy ...
From $511 per night (USD)VRBO
From $621 per night (USD)Expedia
Golf cart+4BR/3B 2100sq Renovated, Large Pool and deck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Recent Review: " I can’t say enough good stuff about this house and location. We stayed for 7 days and the house was sup ...
From $621 per night (USD)Expedia
From $579 per night (USD)VRBO
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ END OF SUMMER SPECIALS ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to announce that our Coconuts beachfront condo is open! We didn't have any damage to our unit from the re ...
From $579 per night (USD)VRBO
From $254 per night (USD)VRBO
Family Friendly Townhome across Street from Beautiful Gulf Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious 3 bedroom and 3 bathroom townhome in Holmes Beach on Anna Maria Island. Recently remodeled. Beach access is d ...
From $254 per night (USD)VRBO
From $417 per night (USD)VRBO
Steps To The Beach, Private & Heated Pool, Renovated - Now Booking Summer/Fall!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, sleeps 8, private heated pool, steps to the beach Please note that there is a 7 day minimum reservation, ex ...
From $417 per night (USD)VRBO
From $396 per night (USD)VRBO
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 $396 per night (USD)VRBO
From $380 per night (USD)VRBO
NO Busy Roads to Cross to Get to the Beach! 5 min walk to beach! Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
No Sharing! Single Family Home. Free HEATED POOL Nov15-Apr15! Quick 5min walk to the Beach! No A&B sides and NO shared p ...
From $380 per night (USD)VRBO
From $234 per night (USD)VRBO
Gulfside 1Br/1Ba Captain's Quarters 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 $234 per night (USD)VRBO
From $293 per night (USD)VRBO
Quiet 3BDR House, Walk to Beach and food, Private Pool and 2 patios to lounge!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private Island Home with heated pool! This is a single whole house. The walk to beach is 4-5 minutes! Call me to arrange ...
From $293 per night (USD)VRBO
From $432 per night (USD)VRBO
Newly renovated home / PRIVATE, NOT SHARED POOL, 6 min. WALK TO BEACH
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated ground-level duplex offers three bedrooms (two king rooms and one twin room with two twin beds). Ju ...
From $432 per night (USD)VRBO
From $885 per night (USD)VRBO
BEACHFRONT HOUSE DIRECTLY ON SOFT SUGAR WHITE SANDS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An amazing beach house literally on the soft white sands of Holmes Beach on Anna Maria Island. As soon as you step out f ...
From $885 per night (USD)VRBO
From $410 per night (USD)VRBO
Island Vibe 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p dir="ltr">Welcome to Island Vibe 1, a renovated 3-bedroom, 2-bathroom home with private, heated and cooled pool plus ...
From $410 per night (USD)VRBO
From $328 per night (USD)VRBO
Gulf views from unit, 1 minute walk to beach, heated pool. SPECIAL RATE
- 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 set up for Sat-Sat ...
From $328 per night (USD)VRBO
From $299 per night (USD)Expedia
Gulf-side 1BR--75 Steps to Sand, Private Patio, Family-Owned Since 1971
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into Old Florida charm with modern comfort at Bamboo Apartments #3, just 75 steps to the sand, with no streets to c ...
From $299 per night (USD)Expedia
From $308 per night (USD)VRBO
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrill ...
From $308 per night (USD)VRBO
From $760 per night (USD)Expedia
Footprints in the Sand managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
114 48th Street Holmes Beach, FL 34217 This absolutely gorgeous 4 bedrooms 3 bathroom home is located in the heart of A ...
From $760 per night (USD)Expedia
From $811 per night (USD)VRBO
Coastal Charm Meets Cottage Chic! Sparkling Pool/Spa *4 Doors To The Beach*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DUE TO HURRICANE HELENE, PROPERTY IS CURRENTLY UNDER RENOVATION. PHOTOS WILL BE UPDATED ONCE COMPLETE! **PLEASE CONTAC ...
From $811 per night (USD)VRBO
From $458 per night (USD)Expedia
1 Block to Beach on Private Lake Heated Pool, SPA 6937 Holmes Blvd.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WE ONLY RENT FROM SATURDAY TO SATURDAY WITH A 7 NIGHT MINIMUM!! 6937 Holmes Blvd, Holmes Beach, FL 34217. Google us for ...
From $458 per night (USD)Expedia
From $305 per night (USD)VRBO
Tranquil AMI Resort Unit 4 all amenities! Central Holmes Beach
- 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 $305 per night (USD)VRBO
From $237 per night (USD)VRBO
Tranquil AMI Resort Unit 1 all amenities! Central Holmes Beach
- 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 $237 per night (USD)VRBO
From $1242 per night (USD)VRBO
Prefect Beach Villa with private beach and heated pool. Gulf front at its's best
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your Dream Beach House on Anna Maria Island! Enjoy your vacation in our beautiful beach house, located at the end of a ...
From $1242 per night (USD)VRBO
From $255 per night (USD)VRBO
Tranquil AMI Resort Unit 3 all amenities! Central Holmes Beach
- 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 $255 per night (USD)VRBO
From $266 per night (USD)VRBO
Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Open now! No hurricane damage and post-hurricane upgrades. All photos were taken post-hurricane. Our Island Retreat cott ...
From $266 per night (USD)VRBO
From $308 per night (USD)Expedia
Anna Maria 2 Family Home w/ pool, beach/3 blocks.
- Bedrooms:
- 2
- 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 $308 per night (USD)Expedia
From $221 per night (USD)VRBO
Summer Special! Cute ground-level Villa, Pet Friendly and so close to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This cute Villa in Holmes Beach is a perfect getaway nestled in a quiet neighborhood. Come relax for a week in this 2bed ...
From $221 per night (USD)VRBO
From $220 per night (USD)Expedia
120 m² condominium with nice afternoon sun
- Bedrooms:
- 2
- 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 $220 per night (USD)Expedia
From $791 per night (USD)VRBO
Direct Beachfront Cottage On Gulf Of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This two story gulf front private home has 3 bedroom/2 baths with fun Carribean decor. This ground level home allows you ...
From $791 per night (USD)VRBO
From $340 per night (USD)Expedia
Paradise Palms: Paradise Awaits, Heated Pool, Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Updated Photos July 2025*** Step into your own private paradise at this beautifully renovated 3-bedroom, 2-bath getaw ...
From $340 per night (USD)Expedia
From $355 per night (USD)VRBO
Gulf Sands 103, 2B/2B Beachfront condo on Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly remodeled. Beautiful turquoise Gulf of Mexico waters, 7 miles of white sand beach, your own private balcony overl ...
From $355 per night (USD)VRBO
From $210 per night (USD)Expedia
Beach pool House Family Vacation Home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a privately owned side by side property, nothing is shared . Private driveway/ garage / Pool and fenced in back ...
From $210 per night (USD)Expedia
From $411 per night (USD)VRBO
Completely Renovated Post Hurricanes w/ heated pool, 5 min walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sandy Palms…. COMPLETELY RENOVATED AFTER THE 2024 STORMS with new drywall, electrical, plumbing, cabinets, ...
From $411 per night (USD)VRBO
From $291 per night (USD)VRBO
Townhouse/ 125 Steps to the Gulf of Mexico. We welcome long term guests.
- Bedrooms:
- 1
- 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 $291 per night (USD)VRBO
From $316 per night (USD)VRBO
Tropical Paradise On The Beach Permit VRC17-000168
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This quaint cottage is located "on the beach" - 3007 Avenue F Unit 4 at 30th Street on beautiful Holmes Beach. It is t ...
From $316 per night (USD)VRBO
Click For PricingExpedia
Gulf Front one bedroom during the New Years holiday 12/29 through 1/3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Island's Homes Beach is like a peaceful desert island, but with every amenity. If you ling for civilization, ...
Click For PricingExpedia
From $1020 per night (USD)VRBO
Above it All: Rooftop Deck Gulf Views, Pool, 5 Homes to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Above it All by Anna Maria Life Vacation Rentals 111 81st St, Holmes Beach, FL 34217 What You'll Love About This Home: ...
From $1020 per night (USD)VRBO
From $408 per night (USD)Expedia
Elevated Beach Home with Pool & Spa Steps from Beach - You, Me, and the Sea AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You, Me and the Sea AMI by Anna Maria Island Locals Home in Holmes Beach, FL VRC21-000081 Welcome to You, Me, and the ...
From $408 per night (USD)Expedia
From $631 per night (USD)VRBO
Coral Beach by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome back to Coral Beach! This luxury home has been totally renovated and refurnished in 2025. From the qualit ...
From $631 per night (USD)VRBO
From $520 per night (USD)Expedia
Sea Salt -Beautiful 3 bedroom with private pool & short walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Salt Sea Salt is a beauty! Nestled in the heart of Holmes Beach-just a short 5-minute walk to the world- ...
From $520 per night (USD)Expedia
From $238 per night (USD)VRBO
Villa-style condo with pool on the beach - Condo 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Apartment 1 is located on the lower level, with a private patio in the back, and the ability to walk straight out to the ...
From $238 per night (USD)VRBO
From $246 per night (USD)Expedia
Villa-style condo with pool and beach access - Condo 8
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you are looking for a great place to stay in Anna Maria Island and want to be close to the beach you will love these ...
From $246 per night (USD)Expedia
From $539 per night (USD)VRBO
Hart of the Gulf: Dog Friendly, 2.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hart of the Gulf by Anna Maria Life Vacation Rentals 305 67th St, Holmes Beach, FL 34217 What You'll Love About This Ho ...
From $539 per night (USD)VRBO
From $219 per night (USD)Expedia
West Bay Point Moorings 155 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
West Bay Point Moorings 155 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. VRC#20-000123 ...
From $219 per night (USD)Expedia
From $311 per night (USD)VRBO
Delphina: 2 Bed 2 Bath Water Front Villa Anna Maria Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your classic beach town oasis! AMI is known for its old time feel and elegance. The villa is newly painted ...
From $311 per night (USD)VRBO
From $270 per night (USD)Expedia
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the nightly rate! (This discount is ap ...
From $270 per night (USD)Expedia
From $276 per night (USD)VRBO
TranquiliSea 1: Pet friendly, long term discount, shared resort-style pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 5% discount on the nightly rate. (This discount is app ...
From $276 per night (USD)VRBO
From $259 per night (USD)Expedia
TranquiliSea 2: Pet friendly, long term discount, shared resort-style pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 5% discount on the nightly rate. (This discount is app ...
From $259 per night (USD)Expedia
From $241 per night (USD)VRBO
Canal Front Old Florida Charmer! 2BDRM 2 Full Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Westbay 203 at Westbay Point & Moorings located Bayside in Holmes Beach! Make yourself at home at this Old Fl ...
From $241 per night (USD)VRBO
From $604 per night (USD)Expedia
Serenity Now - Pet-Friendly Retreat w/ Heated Pool, Near Beach & Tropical Oasis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Serenity Now! On Anna Maria Island (Holmes Beach, FL) A Pet-Friendly Tropical Retreat on Anna Maria Island, ...
From $604 per night (USD)Expedia
From $231 per night (USD)VRBO
West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
West Bay Point Moorings 42 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC#20-000124 ...
From $231 per night (USD)VRBO
From $348 per night (USD)Expedia
GREAT LOCATION! Peaceful & Tropical Condo Steps to Beautiful Holmes Beach, AMI!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly remodeled! 2 BR and 1.5 BA second-level condo just steps to the white sand and turquoise waters of Holmes Beach on ...
From $348 per night (USD)Expedia
From $304 per night (USD)VRBO
6250 Holmes North Beach Village - Condo 2 Bedroom /2.5 Bath , maximum...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful Professionally Decorated Villa with community pool, 3 minute walk to beach 6250 Holmes Boulevard ...
From $304 per night (USD)VRBO
From $171 per night (USD)Expedia
Island Duplex unit: 2-bed/2-bath close to beach, pets welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Updated island duplex (Side A only). Our home is just off Gulf Dr and walkable to the beach (3 blocks), Holmes Beach ci ...
From $171 per night (USD)Expedia
From $390 per night (USD)VRBO
Gulf Place Unit 14 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the epitome of coastal luxury at Gulf Place Unit 14, boasting a stunning beach view and pool access just step ...
From $390 per night (USD)VRBO
From $592 per night (USD)Expedia
Large Private Duplex, Heated Pool and Spa, Outdoor Kitchen and TV
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Breezy Beach by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000336 Plan your dream escape to Breezy Beach ...
From $592 per night (USD)Expedia
From $336 per night (USD)VRBO
AMI Home with Private Pool, 5 Minutes to the Beach! - Hawaiian Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hawaiian Hideaway by Anna Maria Vacations Holmes Beach Private Retreat with Pool VRC16-000298 Welcome to Hawaiian Hid ...
From $336 per night (USD)VRBO
From $625 per night (USD)Expedia
Private Beach Home with Pool, Two Primary Suites, Close to Beach - Coral Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Coral Retreat by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000353 Welcome to Coral Retreat, a vibrant ...
From $625 per night (USD)Expedia
From $499 per night (USD)VRBO
Home with Private Pool, 8 minute walk to Beach! - Villa Portofino
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Portofino by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000358 Villa Portofino is a Mediterranean ...
From $499 per night (USD)VRBO
From $368 per night (USD)Expedia
Home near the beach! Private Pool and Ping Pong Table. - Beachwalk
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beachwalk by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC18-000119 Welcome to Beachwalk, a lovely three-l ...
From $368 per night (USD)Expedia
From $756 per night (USD)VRBO
Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Caribbean Dream by Anna Maria Vacations Private Home in Holmes Beach, FL Embark on an unforgettable retreat at Caribbea ...
From $756 per night (USD)VRBO
From $500 per night (USD)Expedia
Beach Home with Pool, Tiki Bar, and Game Room! Close to Beach - Mango Breeze
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mango Breeze by Anna Maria Vacations 141 50th Street, Holmes Beach, Florida 34217 VRC17-000130 Welcome to Mango Breeze ...
From $500 per night (USD)Expedia
From $512 per night (USD)VRBO
Coconut Cottage: Pool & Spa,1 Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Cottage by Anna Maria Life Vacation Rentals 207 67th St., Holmes Beach, FL 34217 What You'll Love About This Ho ...
From $512 per night (USD)VRBO
From $336 per night (USD)Expedia
Turtle Tyme 2: 1.5 blocks to beach! Private Pool, 3 Putting Greens by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
203 73rd St, Holmes Beach, FL 34217 What You'll Love About this Home: Location! 1 Block to the Beach! 2 Bedrooms / 2 Ba ...
From $336 per night (USD)Expedia
From $238 per night (USD)VRBO
West Bay Point Moorings 286 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath ,...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
West Bay Point Moorings 286 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. VRC#22-000237 ...
From $238 per night (USD)VRBO
From $388 per night (USD)VRBO
Island Vibe 4: Close to Beach with Private Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Island Vibe 4! This ground-level, 3-bedroom, 3-bathroom single-family home has a private, heated and cooled p ...
From $388 per night (USD)VRBO
From $525 per night (USD)VRBO
Beach Front, Ocean Views, Heated Pool, Tennis & Beach Deck! Recently Renovated.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our vacation home, “Almost Heaven”! We believe you will agree with our name once you visit this gem on Anna ...
From $525 per night (USD)VRBO
From $281 per night (USD)Expedia
Coastal 2BDRM Townhouse 100 Steps to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Beach House 102! This sparkling clean and bright 2 bedroom condo is directly across the street from the beach ...
From $281 per night (USD)Expedia
From $282 per night (USD)VRBO
Enjoy Sunsets at Fully Equipped 2BR at the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach House 104! Wake up in this bright townhome located right in the heart of Holmes Beach, just steps from ...
From $282 per night (USD)VRBO
From $764 per night (USD)Expedia
La Plage #1: Gulf Views! Heated Pool & Spa! Elevator by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
LaPlage #1 by Anna Maria Life Vacation Rentals 6430 Gulf Dr, #1, Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $764 per night (USD)Expedia
Click For PricingVRBO
Breezes Family Beach House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3-MINUTE WALK TO THE BEACH!!! Spacious and unique accommodation, Breezes Beach House boasts 4 bedrooms and 3 bathrooms. ...
Click For PricingVRBO
From $449 per night (USD)Expedia
Beachfront - Sea View Play by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A picture is worth a thousand words, and you'll have plenty of photo-ops from your spacious, screened-in, second story b ...
From $449 per night (USD)Expedia
From $332 per night (USD)VRBO
Laid-Back Island Home with Pool | Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private Palms by AMI Accommodations 132 48th St, Holmes Beach, Florida 34217 Welcome to Private Palms, a beautifully ...
From $332 per night (USD)VRBO
From $846 per night (USD)Expedia
Coastal Home with Pool and Jetted Spa! Close to Beach! - Blue Coral Beach House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Coral Beach House by AMI Locals Holmes Beach Coastal Retreat with Private Pool VRC23-000024 Welcome to Blue Cora ...
From $846 per night (USD)Expedia
From $466 per night (USD)VRBO
Private Pool - Carefree Cottage by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where a ...
From $466 per night (USD)VRBO
From $726 per night (USD)Expedia
Starfish Cottage: 1 Block to the Beach! Heated Pool, 4 King Beds by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Starfish Cottage by Anna Maria Life Vacation Rentals 202 64th St, Holmes Beach, FL 34217 What You'll Love About This Ho ...
From $726 per night (USD)Expedia
From $451 per night (USD)VRBO
Beauty & The Beach: 1.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beauty & the Beach by Anna Maria Life Vacation Rentals 205 73rd St, Holmes Beach, FL 34217 What You'll Love About This ...
From $451 per night (USD)VRBO
From $511 per night (USD)Expedia
Private Home with Private Pool and Spa! New Renovations! Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Calypso Cottage by Anna Maria Vacations Holmes Beach Beach Retreat with Pool and Tickle Table VRC16-000622 Your islan ...
From $511 per night (USD)Expedia