Holmes Beach Rentals
From $294 per night (USD)VRBO
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
- Bedrooms:
- 1
- 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 $294 per night (USD)VRBO
From $409 per night (USD)Expedia
Private Pool, Pets & Beach Days Just Steps Away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Just a 2-minute walk to the Gulf beaches • Private heated pool • Tropical tiki patio • 2 Bedrooms ...
From $409 per night (USD)Expedia
From $210 per night (USD)VRBO
A Wright Place · Saltwater Pool · 2.5 Blocks · Pets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000511 2BR + Den · 2BA · Sleeps 6 · Heated Saltwater Pool · Reading Nook · Gas Grill · Pet-Friendly ($150 · 1 Sma ...
From $210 per night (USD)VRBO
From $542 per night (USD)Expedia
Breakers 1 · Old Florida Home · Gulf Front - Fully Restored
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000530 3BR · 2.5BA · Sleeps 6 · Direct Gulf Front · Private Deck · Post-Hurricane 2025 Restoration · New Kitchen ...
From $542 per night (USD)Expedia
From $377 per night (USD)VRBO
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 $377 per night (USD)VRBO
From $526 per night (USD)Expedia
Private Poolside Paradise & AMI Adventures
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Just a 6-minute walk to Anna Maria Island's Gulf beaches • Private heated pool surrounded by tro ...
From $526 per night (USD)Expedia
From $356 per night (USD)VRBO
Holmes Beach Cottage Steps to the Beach with Heated Pool!
- Bedrooms:
- 1
- 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 $356 per night (USD)VRBO
From $309 per night (USD)Expedia
SS Salamander South · 2 Full Baths · Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
VRC16-000500 2BR · 2BA · Sleeps 5 · Very Short Walk to Gulf · Two Full Bathrooms · Heated Pool · Gas Grill · Outdoor Se ...
From $309 per night (USD)Expedia
From $292 per night (USD)VRBO
Peace 'n Paradise · Pool & Spa · 300 Yds Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC20-000280 2BR · 2BA · Sleeps 6 · Private Heated Pool & Spa · 300 Yards to Gulf · Gas Grill · Beach Cart & Full Gear ...
From $292 per night (USD)VRBO
From $257 per night (USD)Expedia
Sea Pirate 3 · 50 Sec to Beach · 2025 Remodel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000556 2BR · 1BA · Sleeps 6 · 50 Seconds to Gulf · 2025 Remodel · 712 Sq Ft + 326 Sq Ft outdoor Patio · Full/Full ...
From $257 per night (USD)Expedia
From $293 per night (USD)VRBO
Beach Days & Dog-Friendly AM Island Adventures
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Short walk to the Gulf beaches via North Beach Village • Quiet residential location • 2 Bedroom ...
From $293 per night (USD)VRBO
From $580 per night (USD)Expedia
Beachside · Saltwater Pool & Spa · Gulf Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000521 3BR · 2BA · Sleeps 6 · Heated Saltwater Pool · Hot Tub · Fenced Yard · Outdoor Shower · Beach Chairs & Umb ...
From $580 per night (USD)Expedia
From $326 per night (USD)VRBO
Breakers 3 · Gulf Front · 28-Night Minimum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC20-000178 3BR · 2BA · Sleeps 8 · Direct Gulf Front · Elevated Position · Full-Length Deck · Private Sand Path to Bea ...
From $326 per night (USD)VRBO
From $668 per night (USD)Expedia
One house to the Beach with expansive heated pool!! Sleeps 8
- Bedrooms:
- 4
- 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 $668 per night (USD)Expedia
From $274 per night (USD)VRBO
Seaside Beach House 102 · Gulf Front · For Sale · Families
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC16-000503 1BR · 1.5BA · Sleeps 4 · Gulf Front · Beachfront Balcony · Heated Pool · Pack-N-Play & High Chair · No EVs ...
From $274 per night (USD)VRBO
From $334 per night (USD)Expedia
Seaside Beach House 205 · End Unit · 180° Lanai · Gulf View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000508 2BR · 1.5BA · Sleeps 4 · Gulf-Front · 180° Open Lanai · Gulf Views from Kitchen · Covered Parking · In-Unit ...
From $334 per night (USD)Expedia
From $340 per night (USD)VRBO
Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!
- Bedrooms:
- 1
- 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 $340 per night (USD)VRBO
From $340 per night (USD)Expedia
Beautiful cottage just around the corner from the beach with Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Seahorse Beach House located just a few houses from the Gulf beaches of Anna Maria Island. Seahorse Beach Hou ...
From $340 per night (USD)Expedia
From $424 per night (USD)VRBO
Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Castaway Cottage located 2 houses down from the Gulf beaches of Anna Maria Island. Castaway Cottage is a grou ...
From $424 per night (USD)VRBO
From $340 per night (USD)Expedia
Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Sand Dollar Shack located just a few houses from the Gulf beaches on Anna Maria Island. The Sand Dollar S ...
From $340 per night (USD)Expedia
From $213 per night (USD)VRBO
Cove 208 · Renovated 2023 · Pool & Mangrove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC19-000217 2BR · 2BA · Sleeps 6 · Fall 2023 Renovation · Private Lanai · Pool & Mangrove Views · King Bed · Two Twins ...
From $213 per night (USD)VRBO
From $232 per night (USD)Expedia
MI Happy Place Sea Horse 3 · Pet-Friendly · Manatee Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC19-000207 2BR · 1BA · Sleeps 6 · Pet-Friendly ($150 Fee) · Across from Manatee Public Beach · Late 2024 Renovation · ...
From $232 per night (USD)Expedia
From $232 per night (USD)VRBO
MI Happy Place Sea Turtle 4 · Pet-Friendly · Manatee Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC19-000208 2BR · 1BA · Sleeps 6 · Pet-Friendly ($150 Fee) · Across from Manatee Public Beach · Late 2024 Renovation · ...
From $232 per night (USD)VRBO
From $232 per night (USD)Expedia
MI Happy Sand Dollar 2 · Pet-Friendly · Manatee Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC19-000210 2BR · 1BA · Sleeps 6 · Pet-Friendly ($150 Fee) · Across from Manatee Public Beach · Late 2024 Renovation · ...
From $232 per night (USD)Expedia
From $232 per night (USD)VRBO
MI Happy Place Sand Castle 1 · Pet-Friendly · Manatee Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VRC19-000209 2BR · 1BA · Sleeps 6 · Pet-Friendly ($150 Fee) · Across from Manatee Public Beach · 2024 Renovation · Shar ...
From $232 per night (USD)VRBO
From $784 per night (USD)Expedia
Absolutely Perfect · Gulf Front · Private Beach Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VRC16-000512 4BR · 3.5BA · Sleeps 8 · Private Beach · Heated Pool · Outdoor Kitchen · Rooftop Deck · Media Room · Gulf ...
From $784 per night (USD)Expedia
From $293 per night (USD)VRBO
Gulfsands 201 · Manatee Beach · Elevator · Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000492 2BR · 2BA · Sleeps 6 · Direct Gulf Front · Adjacent to Manatee Public Beach · Elevator · Heated Pool · Bun ...
From $293 per night (USD)VRBO
From $249 per night (USD)Expedia
Fountainhead 4 · 3 Lanais · Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000542 2BR · 2BA · Sleeps 4 · Three Private Lanais · Heated Pool · Queen Bed · Two Twin Beds · 3-5 Min Walk to Gu ...
From $249 per night (USD)Expedia
From $243 per night (USD)VRBO
Anna Maria Beach Place #6. Directly Across Street From The Beach With Pool.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC21-000063 Anna Maria Beach Place 6 is thoroughly cleaned and sanitized prior to your arrival. We pay special attenti ...
From $243 per night (USD)VRBO
From $340 per night (USD)Expedia
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Surf Camp Cottage located just 3 houses down from the Gulf beaches of Anna Maria Island. Surf Camp Cottage is ...
From $340 per night (USD)Expedia
From $391 per night (USD)VRBO
Ground Floor home for 5, short walk to beach and private heated pool! Lovely open living area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Citrus Cottage located steps from the Gulf beaches of Anna Maria Island. Citrus Cottage is a ground level hal ...
From $391 per night (USD)VRBO
From $296 per night (USD)Expedia
Palm Cay 5. Steps to Beach · 2025 Updates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000555 3BR · 2BA · Sleeps 6 · 71 Steps to Gulf · 2025 Updates · Two King Beds · Twin Room · Heated Pool · On-Site ...
From $296 per night (USD)Expedia
From $371 per night (USD)VRBO
Seaside Beach House 101 · Dolphins from Balcony · Gulf Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000502 2BR · 2BA · Sleeps 4 · Gulf Front · Heated Pool Overlooking Shoreline · Dolphins from Balcony · 10-Unit Bu ...
From $371 per night (USD)VRBO
From $619 per night (USD)Expedia
Coastal Luxury on the Gulf | Pool, Tennis & Trolley Beachfront Bliss on Anna Maria Island | Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Wake up to breathtaking Gulf views and end each day with unforgettable sunsets from this ...
From $619 per night (USD)Expedia
From $334 per night (USD)VRBO
Seaside Beach House 105 · End Unit · 180° Lanai · Gulf View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000506 2BR · 1.5BA · Sleeps 4 · Gulf-Front End Unit · 180° Open Lanai · Gulf Views from Kitchen · Twin Beds in Gu ...
From $334 per night (USD)VRBO
From $633 per night (USD)Expedia
Beautiful Island Home with Great Amenities, Pool, Grill, located close to the Gulf Beaches
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coconut Hideaway located just steps away from the Gulf beaches of Anna Maria Island. This beach house has a p ...
From $633 per night (USD)Expedia
From $426 per night (USD)VRBO
Tropical Poolside Living Steps from AMI Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Walk to the beach, restaurants & island entertainment • Private heated saltwater pool surrounde ...
From $426 per night (USD)VRBO
From $633 per night (USD)Expedia
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 steps from the Gulf beaches of Anna Maria Island. This beach house has a private pati ...
From $633 per night (USD)Expedia
From $598 per night (USD)VRBO
Bradenton Beach Club unit D | 3/2 Beach Front Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3BR · 2BA · Sleeps 6 · Direct Gulf Front · Private Screened Balcony · Heated Pool · Spa · Bayside Gazebo · Elevator · Wa ...
From $598 per night (USD)VRBO
From $324 per night (USD)Expedia
Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Groovy Gecko Cottage just a few houses down from the Gulf beaches of Anna Maria Island. This cottage is a gro ...
From $324 per night (USD)Expedia
From $405 per night (USD)VRBO
Private Pool, Pets & Beach Days Just Steps Away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Just a 2-minute walk to the Gulf beaches • Private heated pool • Tropical tiki patio • 2 Bedro ...
From $405 per night (USD)VRBO
From $450 per night (USD)Expedia
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 $450 per night (USD)Expedia
From $774 per night (USD)VRBO
Paradise Beach House managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
🌴 Paradise Beach House – Luxury 5-Bedroom Retreat with Pool & Jacuzzi 📍 403 42nd Street, Holmes Beach, FL 34217 🪪 VRC ...
From $774 per night (USD)VRBO
From $199 per night (USD)VRBO
1.5 blocks to Beach. Quiet & Convenient Old Florida Charm.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Adorable cottage-style duplex only 1.5 blocks to beautiful Gulf of Mexico beach in Holmes Beach. 3min. walk to beach ...
From $199 per night (USD)VRBO
From $319 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 $319 per night (USD)VRBO
From $351 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 $351 per night (USD)VRBO
From $267 per night (USD)VRBO
Royal Palm: Pool, 2 Blocks to Beach, Close to Dining & Shopping by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Royal Palm by Anna Maria Life Vacation Rentals 5701 Holmes Blvd, Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $267 per night (USD)VRBO
From $410 per night (USD)Expedia
Tiki Cottage: 2.5 Blocks to Beach, Pool with Swim up Tiki Bar by Anna Maria Live Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tiki Cottage by Anna Maria Life Vacation Rentals 303 64th St, Unit B, Holmes Beach, FL 34217 What You'll Love About Thi ...
From $410 per night (USD)Expedia
From $381 per night (USD)VRBO
Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Happy Place by Anna Maria Life Vacation Rentals 210 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: L ...
From $381 per night (USD)VRBO
From $283 per night (USD)Expedia
Chiki Tiki West: Eclectic Beach House, Tiki Bar & Pool, 2.5 Blocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chiki Tiki West by Anna Maria Life Vacation Rentals 303 64th St, Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $283 per night (USD)Expedia
From $314 per night (USD)VRBO
August Deals • Amazing Location • Private Deck • Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
August Special Savings! Take advantage of discounted August rates and plan one last unforgettable beach getaway before s ...
From $314 per night (USD)VRBO
From $699 per night (USD)Expedia
All July 2026 dates on sale
- 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 $699 per night (USD)Expedia
From $259 per night (USD)VRBO
Casa Sierra 203B - 2BR Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. Th ...
From $259 per night (USD)VRBO
From $240 per night (USD)Expedia
Sugaree - 2bedroom Private Pool Property in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Anna Maria Island vacation rental offers one king bed, two twin beds and a queen sleeper sofa all covered in premiu ...
From $240 per night (USD)Expedia
From $769 per night (USD)VRBO
Paradise Found managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
🌴 Paradise Found - with Pool & Hot Tub 📍 401 42nd Street, Holmes Beach, FL 34217 🪪 VRC17-000010 🏡 5 Bedrooms | 6.5 ...
From $769 per night (USD)VRBO
From $547 per night (USD)Expedia
Coconuts108 - GULFFRONT - 1BR/1BA with pool - By Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Beach Resort 108 is a fully remodeled beachfront condo located directly on the Gulf in Holmes Beach on Anna Mar ...
From $547 per night (USD)Expedia
From $430 per night (USD)VRBO
Chapter 2: Renovated pool home, tiki hut and close to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chapter 2 Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater p ...
From $430 per night (USD)VRBO
From $1047 per night (USD)VRBO
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach
- 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 $1047 per night (USD)VRBO
From $454 per night (USD)VRBO
🌴”Kiwi Cottage at Holmes Beach” - Private Heated Pool +Spa+Walk to the Beach! 🌞
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kiwi Coastal Cottage is under new ownership and every space has been thoughtfully redecorated with a cozy coastal island ...
From $454 per night (USD)VRBO
From $528 per night (USD)Expedia
Island Retreat- Stunning 4 bedroom with private heated pool and walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Retreat 4805 2nd Avenue, Holmes Beach, FL 34217 VRC16-000621 What you will love about this property: • Private po ...
From $528 per night (USD)Expedia
From $168 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 $168 per night (USD)VRBO
From $825 per night (USD)Expedia
Blue Water View- 6 bedrooms with amazing rooftop deck and private heated pool
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Blue Water View 118 50th Street, Holmes Beach, FL 34217 VRC16-000296 What you will love about this property: • 4 houses ...
From $825 per night (USD)Expedia
From $374 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 $374 per night (USD)VRBO
From $924 per night (USD)Expedia
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Pirate’s Dream by AMI Locals Welcome to A Pirate’s Dream by AMI Locals, a grand waterfront retreat that perfectly bl ...
From $924 per night (USD)Expedia
From $259 per night (USD)VRBO
Beautiful Island home, 175 steps to the beach, patio, beach gear and Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your serene retreat at "Beach Beauty," nestled in the heart of Holmes Beach, West of Gulf Drive and only 175 ...
From $259 per night (USD)VRBO
From $516 per night (USD)VRBO
Lazy Palm Cottage, private heated pool, steps to the beach. Sleeps 6.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lazy Palm Cottage is back and better than ever for 2026, welcoming guests for the first time since the storms of 2024. C ...
From $516 per night (USD)VRBO
From $307 per night (USD)VRBO
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly renovated ground level home is ...
From $307 per night (USD)VRBO
From $246 per night (USD)Expedia
Bird of Paradise by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Bird of Paradise is a tr ...
From $246 per night (USD)Expedia
From $276 per night (USD)VRBO
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 $276 per night (USD)VRBO
From $273 per night (USD)Expedia
Lakeside Beach House · Pool · Outdoor Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000807 3BR · 2BA · Sleeps 6 · Private Heated Pool · Outdoor Kitchen · Canal Fishing Pier · Beach Gear Provided · ...
From $273 per night (USD)Expedia
From $656 per night (USD)VRBO
La Casa Costiera Blue Water - Newly Renovated, Top Floor Beachfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AT A GLANCE: - La Casa Costiera Unit #6 Blue Water - Large balcony with Gulf views & spectacular sunsets - Newly renova ...
From $656 per night (USD)VRBO
From $340 per night (USD)Expedia
Charming, Family Friendly Newly Renovated Duplex on Holmes Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/2bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Ann ...
From $340 per night (USD)Expedia
From $353 per night (USD)VRBO
Charming, Family Friendly Newly Renovated Duplex on Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/2bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Ann ...
From $353 per night (USD)VRBO
From $504 per night (USD)Expedia
Beachfront Paradise at Tiffany Place 213 | Heated Pool & Gulf Views | 2 Bd/2 Bath | FREE WIFI & Trolley | Awesome Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a relaxing beachfront getaway at Tiffany Place 213, a beautifully remodeled 2-bedr ...
From $504 per night (USD)Expedia
From $523 per night (USD)VRBO
Beachfront - Sandy Turtle by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $523 per night (USD)VRBO
From $394 per night (USD)Expedia
Anna Maria - Holmes Beach - 3BD 2BTH Home - PRIVATE HEATED POOL - WALK TO BEACH
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AZURE BLISS ! _____ SEE VIDEO TOUR - https://youtu.be/_qqC8sHY85c The incredible location mixed in with all of the ...
From $394 per night (USD)Expedia
From $137 per night (USD)VRBO
RELAX/WORK @ Sunbow Bay! By Beach w/Pools & Pickleball. Clean & newly updated!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Great location!....6 minute walk to the beach, trolley stop in front with Publix across the street. Enjoy this beautifu ...
From $137 per night (USD)VRBO
From $795 per night (USD)Expedia
Beautiful 1 Bedroom Condo with Beach Facing Balcony and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Beachfront #112 by AMI Locals VRC21-000175 Your dream beach vacation starts at Coconuts Beachfront #112, a ...
From $795 per night (USD)Expedia
From $616 per night (USD)VRBO
Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Set on a quiet street near the sand, Mango Bay blends ope ...
From $616 per night (USD)VRBO
From $283 per night (USD)Expedia
Plumeria Villa by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Plumeria Villa at Island Garden Villas, where Old Florida charm meets stylish modern luxury. *Features incl ...
From $283 per night (USD)Expedia
From $189 per night (USD)VRBO
Family Friendly Home, 4 mins to Beach! - Starfish Cove, B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Starfish Cove, B by AMI Locals Duplex in Holmes Beach, FL VRC21-000189 Welcome to Starfish Cove, B, a charming beach-t ...
From $189 per night (USD)VRBO
From $191 per night (USD)Expedia
Dog-Friendly Home! 4 mins to the Beach - Starfish Cove, A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Starfish Cove, A by AMI Locals VRC17-000165 Welcome to Starfish Cove, A, a charming coastal retreat in Holmes Beach! T ...
From $191 per night (USD)Expedia
From $274 per night (USD)VRBO
Kiwi Cabana by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Kiwi Cabana! A 2 bed/2 bath, totally private half duplex with a large heated pool in the heart of Holmes Beac ...
From $274 per night (USD)VRBO
From $214 per night (USD)VRBO
The Palms \"A\" an upstairs unit located in the center district of Holmes Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this upstairs condo unit consisting of 2b/1ba, living, dining area & kitchen with enough sleeping for 6. Condomin ...
From $214 per night (USD)VRBO
From $421 per night (USD)VRBO
Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. Vrc16-000069 Max 1 vehicle ...
From $421 per night (USD)VRBO
From $446 per night (USD)Expedia
Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom/2 Bath gulf front, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Vrc16-000745 Beach/Gulf Front - Communit ...
From $446 per night (USD)Expedia
From $389 per night (USD)VRBO
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $389 per night (USD)VRBO
From $377 per night (USD)Expedia
217 84th - Anna Maria Island- Private home 3 Bedroom/ 2 Bath with private pool , maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Vrc#20-000113 Private Pool - D ...
From $377 per night (USD)Expedia
From $427 per night (USD)VRBO
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath, maximum occupancy of 4 people. Vrc20-000254 Beac ...
From $427 per night (USD)VRBO
From $608 per night (USD)Expedia
Sand Of Times-Beautiful 6 bedrooms with private pool/spa with a water slide
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 VRC18-000007 Sands of Time is a newly built 6 bedroom, 4.5 bathro ...
From $608 per night (USD)Expedia
From $411 per night (USD)VRBO
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath gulf front , maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Gulf/Beach Front - ...
From $411 per night (USD)VRBO
From $414 per night (USD)Expedia
Beach Bliss managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Beach Bliss by Beach Retreats Vacation Rentals 📍 320 64th Street, Holmes Beach, FL 34217 🏡 3 Bedrooms | 3 Bathrooms ...
From $414 per night (USD)Expedia
From $171 per night (USD)VRBO
White Palm-2 bedroom monthly condo getaway awaits you with beautiful bay views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
At a Glance 6500 Flotilla Drive unit 163 VRC20-000149 Newly redecorated condo located on the northeastern Bayfront of ...
From $171 per night (USD)VRBO
From $260 per night (USD)Expedia
Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Vrc16-000289 Distance to the ...
From $260 per night (USD)Expedia
From $420 per night (USD)VRBO
Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...
From $420 per night (USD)VRBO
From $197 per night (USD)VRBO
3 Bed/3 Bath Ground Floor Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy this spacious updated condo in a beautifully landscaped, quiet Bayside complex with heated pool and private pickle ...
From $197 per night (USD)VRBO
From $920 per night (USD)VRBO
Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Copy this link to your browser to see 3D view of Emerald Seas floor plan: https://www.zillow.com/view-3d-home/d7fdf4d1- ...
From $920 per night (USD)VRBO
From $191 per night (USD)Expedia
Beautiful Anna Maria Island Condo & Boat Slip-2BR-2BA-Sleeps4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Condo on Anna Maria Island -2 BR 2 BA With a 25' Boat Slip Wonderful quiet residential area overlooks pool with ...
From $191 per night (USD)Expedia
From $504 per night (USD)VRBO
For Shore: Sleeps 10, steps to beach, heated pool!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
***Photos Updated September 2025*** If you are hoping to stay on the perfect Old Florida island in the perfect beach ho ...
From $504 per night (USD)VRBO
From $239 per night (USD)Expedia
Hibiscus Villa by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Hibiscus Villa at Island Garden Villas, where Old Florida charm blends effortlessly with stylish modern luxur ...
From $239 per night (USD)Expedia