Manatee Area Rentals
From $401 per night (USD)VRBO
Coquina Beach Club 202 - Anna Maria Island- Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Coquina Beach Club 202 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Gulf View Condo - Commun ...
From $401 per night (USD)VRBO
From $821 per night (USD)Expedia
Bay Beauty: Private Intra-Coastal front home with sprawling views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bay Beauty, a charming 4-bedroom, 3-bath waterfront retreat in Bradenton Beach where laid-back island living ...
From $821 per night (USD)Expedia
From $397 per night (USD)VRBO
Bradenton Beach Club 230 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Bradenton Beach Club, Unit 230 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the ...
From $397 per night (USD)VRBO
From $765 per night (USD)Expedia
A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to "A Time Out" - your perfect retreat in paradise! This charming 4-bedroom, 2-bathroom home invites you to expe ...
From $765 per night (USD)Expedia
From $831 per night (USD)VRBO
Lovin' the Sannd: North-end cottage, luxury amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you're looking to escape the hustle and bustle of everyday life, look no further than "Lovin' the SANND". This three ...
From $831 per night (USD)VRBO
From $559 per night (USD)Expedia
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2 Bath with private pool, maximum occupancy of 6 people.
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Distanc ...
From $559 per night (USD)Expedia
From $376 per night (USD)VRBO
Anna Maria Island Club 26, Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 4 people. Community pool, Max 1 vehicle.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Island Club 26 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Front - ...
From $376 per night (USD)VRBO
From $335 per night (USD)Expedia
Gulf Watch 216 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people .
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Watch 216 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Direct Bay View - Heated Commun ...
From $335 per night (USD)Expedia
From $718 per night (USD)VRBO
Havana Cay- Adorable 3 bedroom cottage style- Pool/spa and only 4 houses from be
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Havana Cay 109 Cedar Ave, Anna Maria, FL 34216 What you will love about this property: • Historic 1924 Latin style home ...
From $718 per night (USD)VRBO
From $460 per night (USD)Expedia
Coco's Dream - Waterfront Home w/ Oversized Private Heated Pool, 5 Min to AMI
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful Coco's Dream, a canal front home located just 5 minutes from Anna Maria Island and its award-wi ...
From $460 per night (USD)Expedia
From $527 per night (USD)VRBO
Private Pool 4 bd 3 ba with 2 King Master Suites Sleep 10 near AMI and IMG
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Private Pool home near Anna Maria Island & Sarasota. About 5 miles to Anna Maria Island and 23 miles to Siesta Key Beach ...
From $527 per night (USD)VRBO
From $307 per night (USD)Expedia
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)Expedia
From $336 per night (USD)VRBO
JUST LISTED FOR SNOWBIRD 2026 SEASON-CLOSE TO BEACHES, SHOPS, RESTAURANTS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just listed for the SNOWBIRD season 2026. INQUIRE FOR WINTER RATES AND DATES. This spacious 2 BR split floor plan is loc ...
From $336 per night (USD)VRBO
From $1351 per night (USD)Expedia
Island Escape! Pool, Spa, Ping Pong and Fire Pit for Group Fun
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Sail Away by AMI Locals VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front ...
From $1351 per night (USD)Expedia
From $204 per night (USD)VRBO
Sunset Condo #156 on Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This totally renovated condo offers the Gulf of Mexico across the street (west) and Palma Sola Bay (east) of property wi ...
From $204 per night (USD)VRBO
From $557 per night (USD)Expedia
Beachfront Condo-Amazing Views of the Sunset from Every Room! 2 King/4 twins
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GULF FRONT CONDO - Exquisite, newly constructed 3 bedroom 2 bath direct gulf front condo. Corner, end unit on top floor. ...
From $557 per night (USD)Expedia
From $415 per night (USD)VRBO
Experience Coastal Vibes and Serenity - Your Ultimate Longboat Key Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Paradise at Blue Heron House - Your Perfect Longboat Key Vacation Rental Welcome to Blue Heron House by RVA, a ...
From $415 per night (USD)VRBO
From $435 per night (USD)Expedia
Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to Dock your Boat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Pelican Point is a 3-bedroom, 3-bath canal-front home designed for a relaxed Florida vac ...
From $435 per night (USD)Expedia
From $332 per night (USD)VRBO
Updated 2B/2B with a beautiful view of the bay right from the patio!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views ...
From $332 per night (USD)VRBO
From $261 per night (USD)Expedia
LONGBOAT KEY BEAUTY! This 2/2 unit offers stunning views of the bay! Call today to book your fall vacation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
• Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, st ...
From $261 per night (USD)Expedia
From $707 per night (USD)VRBO
Dix-Sea-Land Delight: Close to beach, private pool, quiet street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dix-Sea-Land Delight is a modern, well-appointed 3-bedroom, 3.5-bathroom retreat in Bradenton Beach, set on a quiet stre ...
From $707 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 $339 per night (USD)VRBO
Step from the Beach.Renovated ground Floor unit 63
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Completely renovated. Everything is new. Amazing location. Charming studio. This condo has patio. Condo management will ...
From $339 per night (USD)VRBO
From $1408 per night (USD)Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Photos Updated September 2025*** Experience the ultimate waterfront getaway at this stunning bayfront property in Ann ...
From $1408 per night (USD)Expedia
From $856 per night (USD)VRBO
Beach Bay Serenity: Pine Ave canal front pool home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Beach Bay Serenity! This gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect p ...
From $856 per night (USD)VRBO
From $523 per night (USD)Expedia
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)Expedia
From $204 per night (USD)VRBO
Beach Waves-Private Beach Access-Heated Pool-Two Balconies-Free Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $204 per night (USD)VRBO
From $283 per night (USD)Expedia
Bayview Inn #101 · Heated Pool · Bridge St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bayview Inn #101 | Newly Remodeled & Steps from Bridge Street Welcome to Bayview Inn #101, a newly remodeled 1-bedroom, ...
From $283 per night (USD)Expedia
From $795 per night (USD)VRBO
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)VRBO
From $256 per night (USD)Expedia
Serene Escape King Master, Minutes to AM Island, IMG & More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
When you stay here you'll enjoy these serene and pastoral park-like grounds with non-stop views of catch and release fis ...
From $256 per night (USD)Expedia
From $466 per night (USD)VRBO
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) The Space Step inside The Cottage on Pine and fee ...
From $466 per night (USD)VRBO
From $616 per night (USD)Expedia
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)Expedia
From $755 per night (USD)VRBO
Bay beauty with heated pool, spa, games, ping pong
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning waterfront Anna Maria Island retreat perfect for families! Enjoy a private heated saltwater pool, hot tub, and ...
From $755 per night (USD)VRBO
From $443 per night (USD)Expedia
Blue Opal - Waterfront Home, Boat Dock, w/ Private Heated Pool, 5 Mins to AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful Blue Opal vacation home. This 3 bedroom and 2 bathroom waterfront and private pool home is idea ...
From $443 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 $387 per night (USD)VRBO
Pond-side Oasis| Pickleball| Pool| Foosball
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Once Upon A Pond by Stayawhilewithus! This fun-filled 4BR/3BA family retreat in Bradenton is just minutes fro ...
From $387 per night (USD)VRBO
From $282 per night (USD)Expedia
Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cute and cozy villa is aptly named "Gladiolus Hideaway"! Recently remodeled, this stylish yet comfy hideaway is t ...
From $282 per night (USD)Expedia
From $290 per night (USD)VRBO
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful ...
From $290 per night (USD)VRBO
From $354 per night (USD)Expedia
Luxury HEATED Salt-Water Pool Oasis Close to Beaches and Downtown!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Completely updated 3 bedroom 3 bathroom home that has been beautifully renovated and furnished in a modern coastal desig ...
From $354 per night (USD)Expedia
From $348 per night (USD)VRBO
Lakeside Retreat! Lakefront Living in Northwest Bradenton w/ Saltwater Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lakeside Retreat truly is a treat! This home is brand new to the rental market with so many extras to make your vacation ...
From $348 per night (USD)VRBO
From $724 per night (USD)Expedia
2nd House from the Beach with No Roads to Cross
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads ...
From $724 per night (USD)Expedia
From $446 per night (USD)VRBO
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)VRBO
From $389 per night (USD)Expedia
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)Expedia
From $377 per night (USD)VRBO
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)VRBO
From $427 per night (USD)Expedia
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)Expedia
From $608 per night (USD)VRBO
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)VRBO
From $411 per night (USD)Expedia
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)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 $395 per night (USD)Expedia
Anna Maria Island Club 31, Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 4 people. Community pool, Max 1 vehicle.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Island Club 31 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Saturday to S ...
From $395 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 $142 per night (USD)Expedia
2 Bd/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Available from May 1, 2026 - December 12, 2026. Beautiful corner unit condo with an abundance of windows located between ...
From $142 per night (USD)Expedia
From $345 per night (USD)VRBO
Viva La Flamingo! 10 Min to Anna Maria, Heated Pool, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Important: This home can sleep a maximum of 6 adults. Welcome to our beautiful Viva La Flamingo home. This approximatel ...
From $345 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 $462 per night (USD)VRBO
Villa Treasure Island - Beautifully Renovated Private Pool Home w/ Hottub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
LOCATED IN A QUIET NEIGHBORHOOD, our elegant Villa Treasure Island is exactly what you've been looking for. Imagine spe ...
From $462 per night (USD)VRBO
From $504 per night (USD)Expedia
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)Expedia
From $334 per night (USD)VRBO
Waterslide & Pool ** Wimpy’s Whereabouts!**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This cute cozy 2 bedroom and 2 full bathroom duplex is completely remodeled. The bedrooms both have king size beds. The ...
From $334 per night (USD)VRBO
From $318 per night (USD)Expedia
WATER SLIDE & POOL ** Sugarcane Hideaway**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 16
This unit has 3 bedroom 2 full baths. The master has a king size bed and on-suite full bathroom. The 2nd bedroom has a q ...
From $318 per night (USD)Expedia
From $319 per night (USD)VRBO
WATER SLIDE & POOL ** SUGAR SHACK**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
It’s welcoming and a completely remodeled cottage. It has everything you need for a relaxing vacation. There are three b ...
From $319 per night (USD)VRBO
From $321 per night (USD)Expedia
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Vrc16-000291 Distance to the ...
From $321 per night (USD)Expedia
From $941 per night (USD)VRBO
Hogfish: Stunning Southern-style large family home, minutes from Tampa Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! Hogfish is a spacious 4 bedroom, 3 ½ bath home within walking distance to Pine Avenue, Ci ...
From $941 per night (USD)VRBO
From $598 per night (USD)Expedia
AMI Peppertree Paradise – Steps to Beach, Pool & Outdoor Oasis Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL) Experience AMI Peppertree Paradise — a light- ...
From $598 per night (USD)Expedia
From $598 per night (USD)VRBO
Endless Summer: Gulf Front, Pool, Views by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Endless Summer AMIC 23 by Anna Maria Life Vacation Rentals 2600 Gulf Drive, #23, Bradenton Beach, FL 34217 What You'll ...
From $598 per night (USD)VRBO
From $329 per night (USD)Expedia
Longbeach Lucky 13: Where Island Time Begins & Relaxation Never Ends by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
No luck needed here to know you've stumbled upon one of the best spots Longboat Key has to offer. Longbeach Lucky 13 by ...
From $329 per night (USD)Expedia
From $277 per night (USD)VRBO
Seaside Beach House 203 · Top Floor · 14-Ft Balcony · Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
VRC20-000296 1BR · 1.5BA · Sleeps 3 · Top Floor · 14-Ft Private Balcony · 950+ Sq Ft · Dolphins from Balcony · No Eleva ...
From $277 per night (USD)VRBO
From $291 per night (USD)Expedia
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea La Vie by Anna Maria Life Vacation Rentals 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $291 per night (USD)Expedia
From $636 per night (USD)VRBO
Private Dock - Manatee Lookout by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of ...
From $636 per night (USD)VRBO
From $426 per night (USD)Expedia
Florida Breeze: Pool home in perfect central location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $426 per night (USD)Expedia
From $235 per night (USD)VRBO
Lazy Days at Runaway Bay 162 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lazy Days at Runaway Bay is the perfect place to take time out and relax at your home away from home. This ground floor ...
From $235 per night (USD)VRBO
From $259 per night (USD)Expedia
Unlimited Golf with membership transfer- Lakewood National
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Premium furnishings penthouse (top floor) condo within highly sought after Lakewood National. Lakewood National is a ful ...
From $259 per night (USD)Expedia
From $346 per night (USD)VRBO
Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $346 per night (USD)VRBO
From $426 per night (USD)Expedia
Sea Spray 4: *Heated Pool *Pet-Friendly *Steps to beach *Shops, dining close
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*** Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of Units located in the North End of Anna ...
From $426 per night (USD)Expedia
From $318 per night (USD)VRBO
August Savings - Perfect Location - Pool + Sundeck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
August Deals! Special discounted rates are available this month. Don’t miss your chance to squeeze in one last summer ge ...
From $318 per night (USD)VRBO
From $436 per night (USD)VRBO
Turtle Nest! Private Heated Pool and Access to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $436 per night (USD)VRBO
From $256 per night (USD)VRBO
Townhome with Private Outdoor Living Space, Community Pool - Sea La Vie
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea La Vie by AMI Locals VRC21-000203 Welcome to the relaxed coastal vibe of Sea La Vie, a modern three-bedroom, three ...
From $256 per night (USD)VRBO
From $2520 per night (USD)Expedia
Sundowner Beach: Luxury Gulf-front, stunning views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Sundowner Beach! This luxury gulf-front property offers everything you need to enjoy the perfect beach getaw ...
From $2520 per night (USD)Expedia
From $338 per night (USD)VRBO
Anna Maria and Beaches minutes away~Pool, boat dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Adorable townhouse just minutes from Anna Maria Island! This 2 bedroom, 1 1/2 bath is fully furnished and ready to be yo ...
From $338 per night (USD)VRBO
From $558 per night (USD)Expedia
#201 Sand Piper: 2B / 2B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spacious and comfortable, the Sand Piper has many appealing qualities and amenities. It boasts a full kitchen complete w ...
From $558 per night (USD)Expedia
From $672 per night (USD)VRBO
Live Oak Lodge | Private heated Pool Home Near Anna Maria Island | Family-Friendly Bradenton Vacation Rental | Sleeps 10 | Dog* (See Note) Allowed
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
**ASK ABOUT LAST MINUTE DEALS! Escape to Live Oak Lodge, a peaceful retreat nestled beneath mature oak trees in northwe ...
From $672 per night (USD)VRBO
From $429 per night (USD)Expedia
Sea Spray 1: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $429 per night (USD)Expedia
From $232 per night (USD)VRBO
SF Shorewalk, near Anna Maria Island Beaches and IMG, Pools, Tennis, Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shorewalk SF. Enjoy this beautiful lake view upstairs 2 Bedroom/2 Bath condo 5 min away from IMG Academy, 15 min to the ...
From $232 per night (USD)VRBO
From $797 per night (USD)Expedia
North Shore Very Walkable to Ami fun
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only ...
From $797 per night (USD)Expedia
From $556 per night (USD)VRBO
Seahorse Cottage! Walk to Beach & Shops!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seahorse Cottage by AMI Locals VRC16-000110 Welcome to Seahorse Cottage, a beautifully designed three-bedroom, three ...
From $556 per night (USD)VRBO
From $252 per night (USD)Expedia
The Island Easy - Walk to Beach - Pool View Balcony - Dog Friendly - King Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Island Easy, a dog-friendly, one-bedroom condo on Anna Maria Island just a short walk from the beach. Per ...
From $252 per night (USD)Expedia
From $331 per night (USD)VRBO
Exquisite Beachfront Condo with both Sunrise & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover a newly renovated beachfront sanctuary where Tommy Bahama-inspired style meets modern luxury. This 4th-floor re ...
From $331 per night (USD)VRBO
From $511 per night (USD)Expedia
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
AMI Retreat by Anna Maria Life Vacation Rentals 746 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $511 per night (USD)Expedia
From $500 per night (USD)VRBO
Waterfront on Anna Maria Sound ~ Beaches just minutes away!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this spacious three-bedroom, three bath condo with 10 ft ceilings featuring the finest sunsets and water view ...
From $500 per night (USD)VRBO
From $380 per night (USD)Expedia
Tropical and Tranquil Bradenton hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*FRESHLY UPDATED* 2 Bedrooms, 2 Bath PROPERTY OVERVIEW Located on a peaceful street within 9 miles of the beaches as wel ...
From $380 per night (USD)Expedia
From $713 per night (USD)VRBO
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lazy Lagoon by Anna Maria Life Vacation Rentals 220 Chilson Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $713 per night (USD)VRBO
From $359 per night (USD)Expedia
Island Time: Gulf front condo 20 ft to the beach with shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $359 per night (USD)Expedia
From $589 per night (USD)VRBO
Heated Pool + Ping-Pong + Foosball + 12 min to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Coastal Farmhouse Sarasota! Your ideal family getaway is just two blocks from Sarasota Bay and minutes from ...
From $589 per night (USD)VRBO
From $153 per night (USD)VRBO
Beautiful, Newer Home in River Strand! Endless Fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newer home, with all new indoor and outdoor furniture. This home truly has it all! Luxury and comfort. Located in the ga ...
From $153 per night (USD)VRBO
From $124 per night (USD)VRBO
Nice studio near Anna Maria Island, IMG Academy, UTC Mall, Lecom Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
After a devastating fire almost destroyed our house and studio apartment, and after a 16 months of fighting with insuran ...
From $124 per night (USD)VRBO
From $352 per night (USD)VRBO
Villa Palma Sola - Family Heated Screened Pool, 10 Mins to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Villa Palma Sola, a spacious 3-bedroom, 2-bathroom vacation home with private pool, located in the quiet and ...
From $352 per night (USD)VRBO
From $1732 per night (USD)VRBO
Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the G ...
From $1732 per night (USD)VRBO
From $348 per night (USD)Expedia
Cozy AMI Escape, Steps to Beach & Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Short walk to the beach • 2 Bedrooms | 2 Bathrooms | Sleeps 6 • King primary suite • Queen bed ...
From $348 per night (USD)Expedia
From $756 per night (USD)VRBO
Glad Tidings: Heated pool, turfed outdoor lounge and dining area.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Photos updated March 2025! Welcome to Glad Tidings, a comfortable and well-appointed vacation home on Anna Maria Island ...
From $756 per night (USD)VRBO
From $381 per night (USD)Expedia
St. Lucia - 2 Bedroom/2 Bathroom, Heated Pool, 40 ft. Boat Dock with Water Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to St. Lucia, a waterfront single family house beautifully decorated in 2020 and again in 2025. This private poo ...
From $381 per night (USD)Expedia
From $232 per night (USD)VRBO
PN Shorewalk, near Anna Maria Island Beaches and IMG, Pools, Tennis, Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shorewalk PN. Enjoy this beautiful lake view ground floor 2 Bedroom/2 Bath condo 5 min away from IMG Academy, 15 min to ...
From $232 per night (USD)VRBO
From $432 per night (USD)Expedia
Private Bayside Property -- With Private Fishing/Boating Pier/Remote Office
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The big water view and private pier make this the perfect get-away for anyone who loves to fish, kayak, paddle board, bo ...
From $432 per night (USD)Expedia