Holmes Beach Rentals
From $350 per night (USD)VRBO
Modern Coastal Retreat, Tropical outdoor oasis with private pool and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Serendipity, your perfect beach escape nestled in the charming coastal community of Holmes Beach, Florida. Th ...
From $350 per night (USD)VRBO
From $182 per night (USD)Expedia
West Bay Cove 213 · 3 Blks to Beach · 30-Night
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC20-000269 2BR · 2BA · Sleeps 4 · 1,229 Sq Ft · 30-Night Minimum · 3 Blocks to Manatee Beach · In-Unit Laundry · Sun ...
From $182 per night (USD)Expedia
From $578 per night (USD)VRBO
Nautilus #111 by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Nautilus #111!This newly renovated and decorated gulf front condo has 2 bedroom and 2 bathroom; this vacation ...
From $578 per night (USD)VRBO
From $389 per night (USD)Expedia
dreAMI - Luxury Island Home - Anna Maria - By Island Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
“dreAMI” 12 Palm Harbor Drive is a quintessential island home located in the city of Holmes Beach, and sports all the cl ...
From $389 per night (USD)Expedia
From $411 per night (USD)VRBO
The Pink House - Walking Distance to the Beach and Restaurants
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Pink House – a charming original island cottage on beautiful Anna Maria Island, freshly renovated to blen ...
From $411 per night (USD)VRBO
From $194 per night (USD)Expedia
Delphina in Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Delphina by Anna Maria Island Accommodations Welcome to Delphina, a charming two-bedroom, two-bath waterfront villa nes ...
From $194 per night (USD)Expedia
From $231 per night (USD)VRBO
1-bedroom home with short walk to beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming beach house just minutes from the sugar-white sands of the Manatee Beach! This beautifully decor ...
From $231 per night (USD)VRBO
From $211 per night (USD)Expedia
Fantastic 1-bedroom home, short walk to beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming beach home just minutes from the sugar-white sands of the Manatee Beach! This beautifully decor ...
From $211 per night (USD)Expedia
From $801 per night (USD)VRBO
New Home Sandy Point managed by Beach Retreats FL
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Just steps from the sugar-white sands of Anna Maria Island, Sandy Point is a brand-new beach retreat in Bradenton Beach ...
From $801 per night (USD)VRBO
From $461 per night (USD)Expedia
Sapphire Serenity · Glass Walls · Pool · 30-Night
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VRC25-000156 3BR + Bonus Room · 3BA · Sleeps 6 · 30-Night Minimum · Retractable Glass Walls · Heated Pool · Three Casca ...
From $461 per night (USD)Expedia
From $416 per night (USD)VRBO
Makin Memories Retreat - Private Waterfront Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Makin Memories Retreat, a waterfront getaway designed for families, friends, and anyone looking to experience ...
From $416 per night (USD)VRBO
From $527 per night (USD)Expedia
2BR Family Condo · Heated Pool · Steps to Sand
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Coconuts 117 is a renovated, top-floor 2-bedroom built for families — a king, two queens, and a sleeper sofa, plus two f ...
From $527 per night (USD)Expedia
From $551 per night (USD)VRBO
Spacious 4-bedroom Bayfront Home: Dock, Heated Pool, Dolphins and Manatees
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Some mornings, manatees drift past your private dock - an ordinary day at Infinite Views, a Bayfront home directly on T ...
From $551 per night (USD)VRBO
From $504 per night (USD)Expedia
Romantic 1-bedroom Poolside Villa · Heated Pool · Steps to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out your door and you’re poolside. Coconuts 102 is a single-story villa in a quiet corner of Holmes Beach, the heat ...
From $504 per night (USD)Expedia
From $980 per night (USD)VRBO
Latitude 27 Paradise- Luxury 4 bedroom
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Latitude 27 Paradise 401 77th Street, Holmes Beach, FL 34217 What you will love about this property: • Luxury home with ...
From $980 per night (USD)VRBO
From $658 per night (USD)Expedia
4-bedroom House/ 2-min Walk to Beach · Heated Pool/Spa · Quiet Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
On the quiet end of Holmes Beach, Palm Resort is a fully renovated, ground-level home a short walk from a calm stretch o ...
From $658 per night (USD)Expedia
From $627 per night (USD)VRBO
NEW LISTING! Barefoot Bliss, Gulf Views, Heated Pool & Spa, Golf Cart Incl, Game Rm, Tiki Bar, Sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New to the rental market! Welcome to Barefoot Bliss — a vibrant, welcoming island retreat designed to help you relax, re ...
From $627 per night (USD)VRBO
From $166 per night (USD)Expedia
Surfer Girl - Cute and Cozy Bungalow close to the beach with direct beach access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
New listing!! Looking for an affordable getaway on Anna Maria Island? Enjoy an endless summer at this cute and cozy 1 ...
From $166 per night (USD)Expedia
From $278 per night (USD)VRBO
Make Beach Memories Luxury AMI House Steps to Sand
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to The Coralux Unit A, a luxury Anna Maria Island vacation rental in prestigious Holmes Beach, Florida. Experienc ...
From $278 per night (USD)VRBO
From $274 per night (USD)Expedia
Make Beach Memories - Luxury AMI 2BR Beach House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to The Coralux Unit B, a luxury Anna Maria Island vacation rental in prestigious Holmes Beach, Florida. Experienc ...
From $274 per night (USD)Expedia
From $424 per night (USD)VRBO
Barefoot Energy: Across the street from Gulf! Rooftop Deck Pool & Spa by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Barefoot Energy by Anna Maria Life Vacation Rentals 5613 Gulf Drive, Holmes Beach, FL 34217 What You'll Love About This ...
From $424 per night (USD)VRBO
From $1109 per night (USD)Expedia
Island Life Villa | 5 Bed, Waterfront, Private Pool with Boat Dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
During High Season, reservations typically run Saturday to Saturday. If your preferred dates fall outside these arrival ...
From $1109 per night (USD)Expedia
From $773 per night (USD)VRBO
Conch House~Waterslide, Pool/Spa
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Conch House is a 6BR/4.5BA island retreat just 2.5 blocks to Holmes Beach 🏖️! Enjoy a heated pool with sun sh ...
From $773 per night (USD)VRBO
From $962 per night (USD)Expedia
New!~Heated Pool! Steps to the Beach! Sailfish
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 🌴✨ Villa 1 Sailfish is a charming 2BR/2BA poolside villa at Islands West Resort, just a 2-minute walk to Holm ...
From $962 per night (USD)Expedia
From $525 per night (USD)VRBO
Heated Pool! New! Steps to the Beach! Sand Dollar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: 🌴✨ Villa #4 Sand Dollar ✨🌴 Enjoy island charm at this cozy 1BR/1BA retreat at Islands West Resort, just a � ...
From $525 per night (USD)VRBO
From $786 per night (USD)Expedia
Heated Pool! ~New!~Steps to the Beach! Lime Fish
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 🌴 Villa #7 AMI Lime Fish – Your Anna Maria Island getaway! 🌊☀️ This 2BR/2BA beach villa at Islands West Reso ...
From $786 per night (USD)Expedia
From $500 per night (USD)VRBO
New! Heated Pool~Steps to the Beach/Shops~Starfish
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: 🌴 Villa #6 Starfish – Just 2 mins from Holmes Beach! 🐚 This 1BR/1BA villa features a king bed, queen sleeper ...
From $500 per night (USD)VRBO
From $411 per night (USD)Expedia
Best Location! Heated Pool~Steps to Beach/Shops!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: 🌴 Villa #5 Seashell – Your dream beach escape! 🌊☀️ Just 2 mins from Holmes Beach, this 1BR/1BA villa at Isla ...
From $411 per night (USD)Expedia
From $404 per night (USD)VRBO
New! Heated Pool! Sreps to the Beach! Islands West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: 🌴 Villa #3 Seahorse is a cozy yet upscale 1BR/1BA beach bungalow just a 2-minute walk to Holmes Beach 🏖️. Lo ...
From $404 per night (USD)VRBO
From $373 per night (USD)Expedia
MI Island Time in Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
MI Island Time by Anna Maria Island Accommodations Welcome to MI Island Time, Michigan roots with island soul — a spaci ...
From $373 per night (USD)Expedia
From $164 per night (USD)VRBO
Cozy 2-bedroom condo just steps from the beach, in quaint, peaceful Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Westbay Cove! Make yourself at home in this 2-bedroom Holmes Beach condo. The space features a king bed in on ...
From $164 per night (USD)VRBO
From $386 per night (USD)VRBO
Private paradise w/ all beach supplies & toys!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Stay comfortably in Holmes Beach at this 4-bedroom house. The perfect retreat features a king bed, three queen beds, two ...
From $386 per night (USD)VRBO
From $272 per night (USD)VRBO
Waterfront condo with pool and easy access to sugar sand beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Waterfront condo with pool and easy access to sugar sand beach The Space: Find your happy place at this be ...
From $272 per night (USD)VRBO
From $468 per night (USD)Expedia
Historic beach cottage with private pool - walk 1 block to beach & free trolley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Historic beach cottage with private pool - walk 1 block to beach & free trolley The Space: Experience a go ...
From $468 per night (USD)Expedia
From $378 per night (USD)VRBO
Ocean-front condo with WiFi, pool & Gulf views - steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Ocean-front condo with WiFi, pool & Gulf views - steps to the beach The Space: *Please note that this home ...
From $378 per night (USD)VRBO
From $430 per night (USD)Expedia
Lovely family condo with a private heated pool & Gulf view, close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Lovely family condo with a private heated pool & Gulf view, close to the beach The Space: The family condo ...
From $430 per night (USD)Expedia
From $392 per night (USD)VRBO
Updated Beach Escape with Private Pool, Spa & Fast WiFi - Walk to the Gulf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Updated Beach Escape with Private Pool, Spa & Fast WiFi - Walk to the Gulf The Space: Welcome to paradise ...
From $392 per night (USD)VRBO
From $420 per night (USD)Expedia
Modern villa home near Gulf beaches with private heated pool & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Modern home near Gulf beaches with private heated pool & WiFi The Space: Treat yourself and your loved one ...
From $420 per night (USD)Expedia
From $600 per night (USD)VRBO
Spacious double condo w balconies, Gulf views, shared pool & beach access
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Spacious double condo w/ balconies, Gulf views, shared pool & beach access The Space: Spend all day enjoyi ...
From $600 per night (USD)VRBO
From $191 per night (USD)Expedia
Suite near the beach with a full kitchen, shared grill, AC, & WD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Suite near the beach with a full kitchen, shared grill, AC, & W/D The Space: Whether you're hanging ten or ...
From $191 per night (USD)Expedia
From $366 per night (USD)VRBO
Gulf-front condo with Gulf view, beach access, pool, tennis, & balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Gulf-front condo with Gulf view, beach access, pool, tennis, & balcony The Space: Spend all day enjoying b ...
From $366 per night (USD)VRBO
From $428 per night (USD)Expedia
Beautiful lakeside home w upscale amenities, heated private pool & fishing dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful lakeside home w/ upscale amenities, heated private pool & fishing dock The Space: Bring the whol ...
From $428 per night (USD)Expedia
From $298 per night (USD)VRBO
Island villa with heated private pool, tranquil courtyard, easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Island villa with heated private pool, tranquil courtyard, easy beach access The Space: Welcome to your dr ...
From $298 per night (USD)VRBO
From $364 per night (USD)Expedia
Tropical-themed getaway w heated private pool - walk to free trolley, shopping
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Tropical-themed getaway w/ heated private pool - walk to free trolley, shopping The Space: Island Time is ...
From $364 per night (USD)Expedia
From $231 per night (USD)VRBO
Charming island condo with heated pool near beach & trolley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Charming island condo with heated pool near beach & trolley The Space: Welcome to your charming island ret ...
From $231 per night (USD)VRBO
From $480 per night (USD)Expedia
Island-style townhome with WiFi & pool - minutes from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Island-style townhome with WiFi & pool - minutes from the beach The Space: This property has a 7-night sta ...
From $480 per night (USD)Expedia
From $143 per night (USD)VRBO
Seaside family-friendly condo with WiFi, pool & prime location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Seaside family-friendly condo with WiFi, pool & prime location The Space: *Please note that this home only ...
From $143 per night (USD)VRBO
From $400 per night (USD)Expedia
Welcoming condo villa close to the beach with private heated pool & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcoming condo close to the beach with private heated pool & WiFi The Space: Your luxurious dream getaway ...
From $400 per night (USD)Expedia
From $197 per night (USD)VRBO
Suite near the beach & restaurants with covered deck & shared grill
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Suite near the beach & restaurants with covered deck & shared grill The Space: Whether you're hanging ten ...
From $197 per night (USD)VRBO
From $195 per night (USD)Expedia
Serene oceanfront suite with Gulf view, grill, patio, central AC, & WD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Serene oceanfront suite with Gulf view, grill, patio, central AC, & W/D The Space: Escape the everyday and ...
From $195 per night (USD)Expedia
From $159 per night (USD)VRBO
Inviting Condo with Shared Pool, High-Speed WiFi, and Central AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Inviting Condo with Shared Pool, High-Speed WiFi, and Central AC The Space: Spaciously laid out and cooled ...
From $159 per night (USD)VRBO
From $385 per night (USD)Expedia
Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley The Space: Wake up to the s ...
From $385 per night (USD)Expedia
From $127 per night (USD)VRBO
Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits The Space: *Please note that th ...
From $127 per night (USD)VRBO
From $380 per night (USD)Expedia
Casual beachside getaway with pool, and easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Casual beachside getaway with pool, and easy beach access The Space: Leave your responsibilities behind an ...
From $380 per night (USD)Expedia
From $293 per night (USD)VRBO
Recently Renovated 2bd/2ba a block from the beach & steps from the pool on AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Take advantage of everything Anna Maria Island has to offer or lounge on the beach or pool-side all day. This coastal/bo ...
From $293 per night (USD)VRBO
From $266 per night (USD)Expedia
Charming Ground Floor Condo with Shared Pool, High-Speed WiFi, and Central AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Charming Ground Floor Condo with Shared Pool, High-Speed WiFi, and Central AC The Space: Bright & Beachy G ...
From $266 per night (USD)Expedia
From $200 per night (USD)VRBO
Ground-floor home with fast WiFi, shared pool, & central AC - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Ground-floor home with fast WiFi, shared pool, & central AC - close to beach The Space: Outside: the spark ...
From $200 per night (USD)VRBO
From $270 per night (USD)Expedia
Adorable beachfront villa rental in a great location with Gulf access right outside
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Adorable beachfront rental in a great location with Gulf access right outside The Space: This property has ...
From $270 per night (USD)Expedia
From $278 per night (USD)VRBO
Quaint beachfront duplex villa in ideal location with screened lanai & free trolley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Quaint beachfront duplex in ideal location with screened lanai & free trolley The Space: Newly Remodeled B ...
From $278 per night (USD)VRBO
From $199 per night (USD)Expedia
Cozy retreat, steps away from Gulf and beaches, dog friendly, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cozy retreat, steps away from Gulf and beaches, dog friendly, AC The Space: Welcome to the charming town o ...
From $199 per night (USD)Expedia
From $202 per night (USD)VRBO
Comfortable and relaxing with pool and just steps from the beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Comfortable and relaxing with pool and just steps from the beaches The Space: Welcome to your cozy and his ...
From $202 per night (USD)VRBO
From $1118 per night (USD)Expedia
Luxury oceanfront home w/ pool, spa, free parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Luxury 4-bed beachfront home with heated private pool, spa, free parking The Space: Treat yourself to an u ...
From $1118 per night (USD)Expedia
From $238 per night (USD)VRBO
Anna Maria Island condo with heated pool, short walk from the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Anna Maria Island condo with heated pool, short walk from the beach The Space: This island condo is tucked ...
From $238 per night (USD)VRBO
From $175 per night (USD)Expedia
Sweet duplex with WiFi, central AC, & gas grill - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Sweet duplex with WiFi, central AC, & gas grill - close to beach The Space: Your sweet getaway in Holmes B ...
From $175 per night (USD)Expedia
From $209 per night (USD)VRBO
Serene oceanfront suite with Gulf view, grill, patio, central AC, & WD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Serene oceanfront suite with Gulf view, grill, patio, central AC, & W/D The Space: Escape the everyday and ...
From $209 per night (USD)VRBO
From $373 per night (USD)Expedia
Dog-friendly seaside home - heated private pool & spa, great location near beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Dog-friendly seaside home - heated private pool & spa, great location near beach The Space: Welcome to you ...
From $373 per night (USD)Expedia
From $292 per night (USD)VRBO
Breezy house with great location near beach, shopping & dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Breezy house with great location near beach, shopping & dining The Space: Have the Holmes Beach vacation y ...
From $292 per night (USD)VRBO
From $371 per night (USD)Expedia
Upscale condo with large deck & shared pool - just steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Upscale condo with large deck & shared pool - just steps from the beach The Space: The resurfacing is nece ...
From $371 per night (USD)Expedia
From $205 per night (USD)VRBO
Relaxing retreat with pool, steps to the beach, AC and WIFI
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Relaxing retreat with pool, steps to the beach, AC and WIFI The Space: Experience the charm of historic Fl ...
From $205 per night (USD)VRBO
From $300 per night (USD)Expedia
Comfortable island villa with private heated pool, courtyard & easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Comfortable island villa with private heated pool, courtyard & easy beach access The Space: Welcome to you ...
From $300 per night (USD)Expedia
From $195 per night (USD)VRBO
Contemporary dog-friendly home with shared pool - two blocks from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Contemporary dog-friendly home with shared pool - two blocks from the beach The Space: Relaxation and sun- ...
From $195 per night (USD)VRBO
From $808 per night (USD)Expedia
Oceanview getaway with pool & private patio - steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Oceanview getaway with pool & private patio - steps from the beach The Space: Treat yourself to a relaxing ...
From $808 per night (USD)Expedia
From $587 per night (USD)VRBO
Waterfront home with heated pool & spa, patio, grill, & free WiFi - dog-friendly
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly The Space: *Please note t ...
From $587 per night (USD)VRBO
From $423 per night (USD)Expedia
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views The Space: Find yourself ...
From $423 per night (USD)Expedia
From $197 per night (USD)VRBO
Serene oceanfront suite with Gulf view, grill, patio, central AC, & WD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Serene oceanfront suite with Gulf view, grill, patio, central AC, & W/D The Space: Escape the everyday and ...
From $197 per night (USD)VRBO
From $308 per night (USD)Expedia
Beautiful Beach Home Right Near the Water with Private Pool, AC, & Fast WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful Beach Home Right Near the Water with Private Pool, AC, & Fast WiFi The Space: You're going to lo ...
From $308 per night (USD)Expedia
From $500 per night (USD)VRBO
Hidden Palms - Private Pool, Quiet Island Retreat Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hidden Palms! On Anna Maria Island in Holmes Beach, Florida Perfect for: Families, couples, and small groups ...
From $500 per night (USD)VRBO
From $895 per night (USD)Expedia
Tropical Oasis ~ Rooftop Views/Games/Walk to Beach
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: Tropical Oasis is an 8BR/5.5BA island retreat just 2 minutes from the beach 🏖️! Enjoy a heated pool & spa wit ...
From $895 per night (USD)Expedia
From $882 per night (USD)VRBO
Surf View ~ Walk to Beach/Rooftop Deck/Pool
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: Surf View is an 8BR/6BA luxury home just a 5-minute walk to Holmes Beach 🏖️. Enjoy a private pool with spa, w ...
From $882 per night (USD)VRBO
From $469 per night (USD)Expedia
Malibu Beach ~ Waterslide/Rooftop Views/Walk to Beach
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: Malibu Beach is an 8BR/7BA luxury escape just a 5-minute walk to Holmes Beach 🏖️! Enjoy a private pool with h ...
From $469 per night (USD)Expedia
From $974 per night (USD)VRBO
The Palace ~ Walk to Beach/Rooftop Views
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: The Palace is a 7BR/7.5BA luxury retreat just 3 minutes from Holmes Beach 🏖️. Enjoy a private pool & spa with ...
From $974 per night (USD)VRBO
From $431 per night (USD)Expedia
New Listing! Sailfish Nest A – Your Island Retreat with Private Pool and Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sailfish Nest A, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a ...
From $431 per night (USD)Expedia
From $439 per night (USD)VRBO
Coastal Cottage · Private Pool · 2 Blks to Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC19-000259 3BR · 2BA · Sleeps 6 · 2025 Renovation · Private Fenced Heated Pool · 2 Blocks to Gulf · Stainless Kitchen ...
From $439 per night (USD)VRBO
From $734 per night (USD)Expedia
La Dolce Vita in Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to La Dolce Vita, where luxury meets laid back island living in the heart of Holmes Beach. This newly constructe ...
From $734 per night (USD)Expedia
From $395 per night (USD)VRBO
Buddy Beach House by AMI Locals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Buddy Beach House, a beautifully designed four-bedroom, three-bathroom vacation home in the heart of Holmes B ...
From $395 per night (USD)VRBO
From $407 per night (USD)Expedia
Beachfront - Saint Somewhere at Gulf Place 12
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the perfect beach getaway in this beautifully updated 3-bedroom, 2-bath condo, designed to comfortably accommodate ...
From $407 per night (USD)Expedia
From $255 per night (USD)VRBO
Cheerful North Beach Getaway – Walk to Beach + Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
NEW MANAGEMENT! Spend your days at the beach, your afternoons by the pool, and your evenings unwinding at Cheerful North ...
From $255 per night (USD)VRBO
From $628 per night (USD)Expedia
Palms By The Bay by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Palms by the Bay! This beautiful home features three bedrooms plus bonus room and three bathrooms and is loca ...
From $628 per night (USD)Expedia
From $184 per night (USD)VRBO
Sweet Slice of Old Florida Charm with modern amenities, large yard & beach gear
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the charm of "Old Florida" in this inviting island home! You will love the cute and comfortable interior and th ...
From $184 per night (USD)VRBO
From $691 per night (USD)Expedia
Honey I'm Holmes - New Home Near the Beach! Turf
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Honey I’m Holmes! Start your island getaway here at our newly refreshed coastal home in a charming ...
From $691 per night (USD)Expedia
From $238 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, a renovated 2-bedroom, 2-bathroom home with private, heated pool, and a private back yard! T ...
From $238 per night (USD)VRBO
From $268 per night (USD)Expedia
Beachfront Condo w/ Pool & Gulf Views I Anna Maria Island I Seaside Beach Villa | Steps to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to Seaside Beach Villa, a beautifully remodeled 1-bedroom, 1.5-bath beachfront condo located directly on the Gulf ...
From $268 per night (USD)Expedia
From $454 per night (USD)VRBO
Private Pool - Yacht Rock Ranch by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect Holmes Beach getaway! Just a short stroll from some of the best beaches on Anna Maria Island. Th ...
From $454 per night (USD)VRBO
From $246 per night (USD)Expedia
Sunshine Daydream in Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunshine Daydream by Anna Maria Island Accommodations Welcome to Sunshine Daydream, a welcoming three bedroom, two and ...
From $246 per night (USD)Expedia
From $493 per night (USD)VRBO
Hightide Hideout ~ Walk to the Beach • Playground • Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Hightide Hideout — a bright, laid-back coastal bungalow in the heart of Holmes Beach on Anna Maria Island. Th ...
From $493 per night (USD)VRBO
From $1451 per night (USD)Expedia
Limefish Luxury | Gulf Front Pool | Sunset Views | Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Wake to waves and end each day with award-winning Gulf sunsets at Limefish Luxe—a Gulf-front, 3BR/3BA luxury r ...
From $1451 per night (USD)Expedia
From $426 per night (USD)VRBO
Private Pool - Tropical Smiles by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your island retreat in the heart of Holmes Beach, Florida. This pet-friendly property offers a light-filled, ...
From $426 per night (USD)VRBO
From $784 per night (USD)Expedia
Nirvana Sunset~Across from Beach, Heated Pool/Spa!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 🌅 Welcome to Nirvana Sunset 🌴 Located at 2809 Ave E in Holmes Beach, this luxurious 4BR / 4.5BA retreat feat ...
From $784 per night (USD)Expedia
From $652 per night (USD)VRBO
Coconuts 118 | Gulf View Heated Pool • Steps to Sand
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Coconuts 118 is a newly renovated Gulf-View 2-bedroom, 2-bath condo steps from Holmes Beach. Enjoy two private ...
From $652 per night (USD)VRBO
From $421 per night (USD)Expedia
Enclosed pool/spa - Stillpoint by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Stillpoint, a beautifully designed single-level home just one block from the beach in the heart of Holmes Bea ...
From $421 per night (USD)Expedia