Manatee Area Rentals
From $222 per night (USD)VRBO
LOCATION!! Cabana just steps from the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to Anna Maria Island the # 1 spot for a perfect getaway. Bask in the tropical paradise of AMI with white sugar ...
From $222 per night (USD)VRBO
From $235 per night (USD)Expedia
Beachside Oasis at Runaway Bay 229 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come relax and enjoy this stunning 2 bedroom/2 bathroom, second level, recently updated condo at Runaway Bay. Runaway Ba ...
From $235 per night (USD)Expedia
From $435 per night (USD)VRBO
Island Charm, Luxury Location & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Highlights • Just steps from the beautiful Gulf beaches • Private heated pool • 2 King Bedrooms | 2.5 Bathro ...
From $435 per night (USD)VRBO
From $303 per night (USD)Expedia
Salty Harbor AMI pool retreat near the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 ...
From $303 per night (USD)Expedia
From $202 per night (USD)VRBO
Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor only steps to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private Beach Cottage with apartment on second floor. Top floor apartment has two bedrooms, one recently remodeled bath, ...
From $202 per night (USD)VRBO
From $1229 per night (USD)Expedia
Waterfront Home with Pool, Dock, and Rooftop Deck! Short Walk to Beach!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Bayfront Retreat by AMI Locals VPL18-000550, DWE5105473 Welcome to Bayfront Retreat, a boater's paradise with a priva ...
From $1229 per night (USD)Expedia
From $403 per night (USD)VRBO
Best views of the beach from your balcony Unit 301
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to Paradise! Unit 301 with unobstructed Mexican Gulf View. This is a corner condo, so you have more space and a ...
From $403 per night (USD)VRBO
From $242 per night (USD)Expedia
Modern 3BR Home, Near Beaches, Downtown, Golf & IMG
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Clean, Modern 3BR Home | Minutes to Beaches, Downtown & Golf Enjoy everything the Gulf Coast has to offer from this bea ...
From $242 per night (USD)Expedia
From $224 per night (USD)VRBO
Modern 3BR Home, Near Beaches, Golf, Downtown & IMG
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean, Modern 3BR Home | Minutes to Beaches, Downtown & Golf Enjoy everything the Gulf Coast has to offer from this bea ...
From $224 per night (USD)VRBO
From $232 per night (USD)Expedia
BK Shorewalk, near Anna Maria Island Beaches and IMG, Pools, Tennis, Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shorewalk BK. 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)Expedia
From $850 per night (USD)VRBO
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $850 per night (USD)VRBO
From $335 per night (USD)Expedia
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $335 per night (USD)Expedia
From $181 per night (USD)VRBO
Resort Life Lakewood National 2 Golf Courses, Pools, Pickelball, Spa, and more!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our newer fully furnished “Palmer’s Cove” condo at LAKEWOOD NATIONAL Golf & Country Club in beautiful Lakewood ...
From $181 per night (USD)VRBO
From $200 per night (USD)Expedia
Crow's Nest Spinnakers Cottages: 250 Steps to Beach! Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Crow's Nest Spinnakers Cottages by Anna Maria Life Vacation Rentals 202 56th St. #2, Holmes Beach, FL 34217 What You'll ...
From $200 per night (USD)Expedia
From $189 per night (USD)VRBO
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $189 per night (USD)VRBO
From $323 per night (USD)Expedia
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $323 per night (USD)Expedia
From $296 per night (USD)VRBO
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $296 per night (USD)VRBO
From $304 per night (USD)Expedia
Longboat Key Escape – Cedars East #603 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $304 per night (USD)Expedia
From $178 per night (USD)VRBO
2 Bed, 2 Bath, Direct Beachfront w/ Gulf views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachfront Bliss on Longboat Key – Stunning Views & Modern Comfort Stay directly on the beach in this beautifully upd ...
From $178 per night (USD)VRBO
From $135 per night (USD)Expedia
Luxury Resort Amenities & Golf Membership; Pets Welcome; Lakefront Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom, two bathroom condo in the Vardon Terrace Condominium complex-- beautiful view overlooking the Commander Gol ...
From $135 per night (USD)Expedia
From $1784 per night (USD)VRBO
Beaches and Dreams: Ultimate Luxury Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams, where stunning panoramic bay view ...
From $1784 per night (USD)VRBO
From $649 per night (USD)Expedia
Beautiful North end Pool Home with Gulf Views, Heated pool, steps to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are excited to announce that our popular vacation rental is back on the market after a complete renovation! Everythin ...
From $649 per night (USD)Expedia
From $349 per night (USD)VRBO
Experience a resort feel vacation on the beach in Longboat Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedrooms, two baths, (approximately 1500 square feet) with a study, two balconies, an assigned covered parking , loc ...
From $349 per night (USD)VRBO
From $495 per night (USD)Expedia
Unit #208 Sand Cay Beach Resort Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you ...
From $495 per night (USD)Expedia
From $420 per night (USD)VRBO
5 miles from Anna Maria IslandI! Heated pool! Game room and HUGE private yard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Privacy abounds in this beautiful modern home located in an upscale quiet neighborhood. Enjoy spending time with family ...
From $420 per night (USD)VRBO
From $872 per night (USD)Expedia
Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Buttonwood Cottage by AMI Locals Welcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home ...
From $872 per night (USD)Expedia
From $423 per night (USD)VRBO
Bayview Condo A - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 6 people. Community pool. Distance to the Beach: 1 block
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Bayview Condo, Unit A - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Community Pool - Bay View ...
From $423 per night (USD)VRBO
From $356 per night (USD)Expedia
Chic Pool Home Steps to Beach! Game Room and Paddleboards
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Pure Beach by AMI Locals VRC21-000101 Welcome to Pure Beach by AMI Locals, a luxurious three-bedroom, three-bath vaca ...
From $356 per night (USD)Expedia
From $602 per night (USD)VRBO
Point's Hideaway - Luxury Retreat w/ Private Pool & Deck, Stunning Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Point's Hideaway! On Anna Maria Island (Anna Maria, FL) Please note: The home is next to a construction site. ...
From $602 per night (USD)VRBO
From $568 per night (USD)Expedia
Sarasota Paradise Home Near Siesta Key Beach and IMG Academy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This is a peaceful 4-bedroom house with 3 bathrooms located in Sarasota. It features a heated pool and is just a 45-minu ...
From $568 per night (USD)Expedia
From $203 per night (USD)VRBO
Walk across to the Beach or Lounge by the Pool! Paradise is Waiting! Book your holiday vacationtoday!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully remodeled, cozy, 1 bedroom/ 1 bathroom condo is perfect for a romantic getaway! Positioned on the Bay o ...
From $203 per night (USD)VRBO
From $634 per night (USD)Expedia
Luxurious Island Retreat with Pool, Spa and Private Suite
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Freckled Fin by AMI Locals VR19-000006 Welcome to Freckled Fin, a vibrant and luxurious four-bedroom, four-and-a-half ...
From $634 per night (USD)Expedia
From $1144 per night (USD)VRBO
Serendipity Gulfront | Hot Tub | Heated Pool | Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity G ...
From $1144 per night (USD)VRBO
From $1144 per night (USD)Expedia
Tripletail | Beachfront | Pool & Spa | 4 King Beds
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience the ultimate Anna Maria Island getaway at Tripletail! This stunning 4-bedroom, 4-bath bayfront home ...
From $1144 per night (USD)Expedia
From $318 per night (USD)VRBO
One Bedroom Island Luxury Cottage located less than 2 blocks from the beach.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Flop Cottage located 1 block from the Gulf beaches of Anna Maria Island. Flop Cottage is a ground level half ...
From $318 per night (USD)VRBO
From $1244 per night (USD)Expedia
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is in the monthly rental ...
From $1244 per night (USD)Expedia
From $740 per night (USD)VRBO
Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Sand Castle located just a few steps from the Gulf beaches of Anna Maria Island. Built in 1924, the Castl ...
From $740 per night (USD)VRBO
From $402 per night (USD)Expedia
Starfish Cottage - sleeps 4, with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Starfish Cottage is situated towards the top end of Anna Maria Island. The property is extremely well furnished and equi ...
From $402 per night (USD)Expedia
From $577 per night (USD)VRBO
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open for business in 2025! Check out the latest review. OHasis Getaway is a true oasis on both the outside and inside! ...
From $577 per night (USD)VRBO
From $714 per night (USD)Expedia
Luxury Villa · Heated Saltwater Pool & Spa · Steps to Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Prime Location – Steps to the Beach! Luxurious ground-level villa at 124 50th Street, Holmes Beach, in the heart of Anna ...
From $714 per night (USD)Expedia
From $158 per night (USD)VRBO
Cabin 2 Spinnakers Cottages: Dog Friendly - 250 Steps to Beach Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cabin 2 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #2, Holmes Beach, FL 34217 What You'll Lov ...
From $158 per night (USD)VRBO
From $555 per night (USD)Expedia
Luxury Living & Heated Pool Near Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Property Highlights • Fully remodeled luxury home in 2026 • 4 Bedrooms | 3 Bathrooms | Sleeps 8 • Heated saltwater po ...
From $555 per night (USD)Expedia
From $965 per night (USD)VRBO
BUENA VISTA 4 - LUXURY BEACHFRONT - Anna Maria Island - By Island Real Estate Va
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Top 10 Gulfview on Anna Maria Island!!! You can see for miles in both direction down the beach. Luxury condominium “Buen ...
From $965 per night (USD)VRBO
From $1251 per night (USD)Expedia
Buena Vista 3 - DIRECT BEACHFRONT Luxury Condo - Anna Maria Island- By Island Re
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DIRECT BEACH FRONT - Luxury 4BR Condo - Buena Vista #3 - 101 67th Street - 4 Bedrooms and 3 and a 1/2 Baths - Bed/s: 3 ...
From $1251 per night (USD)Expedia
From $383 per night (USD)VRBO
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wake up to peaceful lake views, enjoy your morning coffee on the private lanai, and be just minutes from IMG Academy and ...
From $383 per night (USD)VRBO
From $281 per night (USD)Expedia
Anna Maria Sunsets - studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This condo is at the Tortuga Inn which is the perfect beach-to-bay resort on Florida's unspoiled Ann Maria Island. Plus ...
From $281 per night (USD)Expedia
From $119 per night (USD)VRBO
Country Cottage Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Country Cottage located in a quiet area of Bradenton. Located on private secluded property .The cottage has its own fe ...
From $119 per night (USD)VRBO
From $229 per night (USD)Expedia
Waterfront Unit, Heated Pool, 70\" TV, Tiki Bar & Grill, On The Marina!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Marina Front, Updated Hotel Room-Condo at the Ramada Inn on 41. Ground-floor, Two large, comfy Queen beds, 70" smart TV ...
From $229 per night (USD)Expedia
From $409 per night (USD)VRBO
Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spend your Anna Maria Island vacation in five star luxury when you visit “Aquarius”. This fully renovated Holmes Beach v ...
From $409 per night (USD)VRBO
From $291 per night (USD)Expedia
Breezy Harbor AMI pool retreat near the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for ...
From $291 per night (USD)Expedia
From $454 per night (USD)VRBO
ON the Beach, 2nd Floor, Elevator, Heated swimming pool and Spa, Freshly painted
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service wit ...
From $454 per night (USD)VRBO
From $675 per night (USD)Expedia
BOUTIQUE BEACH FRONT LUXURY LOCATED DIRECTLY ON BEACH WITH FABULOUS SUNSETS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This boutique luxury 5 star rated beach home awaits you for the vacation of a lifetime! ...
From $675 per night (USD)Expedia
From $1131 per night (USD)VRBO
Buena Vista #2: Luxury Beach Front Condo, Amazing Views, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Buena Vista #2 by Anna Maria Life Vacation Rentals 101 67th St #2, Holmes Beach, FL 34217 What You'll Love About This H ...
From $1131 per night (USD)VRBO
From $401 per night (USD)Expedia
Boat Lover's Spacious, 4/3.5 waterfront canal home with Dock and Heated pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Boat Lovers' Paradise! Entertain family and friends in spacious 2400 sqft home with beautiful water front views, privat ...
From $401 per night (USD)Expedia
From $202 per night (USD)VRBO
Modern Beach House, 1 Block from beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Anna Maria Island Vacation Home is located just a few houses from the white sand beaches! Holmes Beach is ...
From $202 per night (USD)VRBO
From $690 per night (USD)Expedia
La Cocolia located north end of Ami, Lagoon Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a Great Ami Getaway? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house ...
From $690 per night (USD)Expedia
From $944 per night (USD)VRBO
GLORIOUS DAZE Beach House POOL! SPA! GOLFCART! ELEVATOR! PUTTING GREEN!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Glorious Daze! Our four bedroom/four bath private home is located along the sugary white sands of beautiful H ...
From $944 per night (USD)VRBO
From $249 per night (USD)Expedia
Sunshine Oasis 2 With Heated Pool. Minutes to Gulf Beaches and IMG
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom 2 bath home in west Bradenton just minutes from beautiful Anna Maria Island with miles of white sandy beaches, ...
From $249 per night (USD)Expedia
From $928 per night (USD)VRBO
Luxury 3BD Beachfront Living: La Playa 203D by RVA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Playa #203D – Gulf-Front Luxury Condo on Longboat Key by RVA Welcome to La Playa #203D, your private beachfront retr ...
From $928 per night (USD)VRBO
From $574 per night (USD)Expedia
The Beautiful House 6/4.5 w/detached residence, Pets+ SUN & FUN, CLOSE TO BEACH
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Check out our heated pool with LED lights, 3 1/2 horse power swim jet for swimming laps and serene rain waterfalls to Th ...
From $574 per night (USD)Expedia
From $298 per night (USD)VRBO
Beautiful 2/2 bay view unit!! End of 2026 dates available!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy some peace in quiet in beautiful Longboat Key. This clean and comfortable 2 bedroom 2 bathroom condo on Saras ...
From $298 per night (USD)VRBO
From $567 per night (USD)Expedia
End of summer sale Take a peek awesome reviews 50 feet from sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...
From $567 per night (USD)Expedia
From $596 per night (USD)VRBO
Late summer sale Client texted view crazy, see reviews
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...
From $596 per night (USD)VRBO
From $235 per night (USD)Expedia
Sea Life at Runaway Bay 211 by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come relax and enjoy this stunning 2 bedroom/2 bathroom second level, recently updated condo at Runaway Bay. Runaway Ba ...
From $235 per night (USD)Expedia
From $860 per night (USD)VRBO
Casa Mariposa – AMI Luxury Retreat Steps to Beach & Pine Ave w/ Pool & Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Mariposa! On Anna Maria Island (Anna Maria, FL) Experience Casa Mariposa where the rhythm of island lif ...
From $860 per night (USD)VRBO
From $246 per night (USD)Expedia
3/2 Home Heated Pool / close to Beautiful Anna Maria Beaches / close to IMG
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌞 A peaceful home is an ideal vacation home for families with multiple generations. 🌞 The house is well-maintained and ...
From $246 per night (USD)Expedia
From $299 per night (USD)VRBO
The Hideaways at Point Pleasant (Pine Side)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Hideaways at Point Pleasant – Downtown Welcome to The Hideaways at Point Pleasant, two beautifully updated cottage ...
From $299 per night (USD)VRBO
From $489 per night (USD)Expedia
Ground Floor Luxury 4BR Home · Heated Saltwater Pool & Spa · Very Close to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to AMI Beach Home in Holmes Beach on beautiful Anna Maria Island. This custom-built ground-floor vacation home ...
From $489 per night (USD)Expedia
From $309 per night (USD)VRBO
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Getaway by Anna Maria Life Vacation Rentals 205 56th St., Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $309 per night (USD)VRBO
From $405 per night (USD)Expedia
Wake up on the waters of Tampa Bay in a north Anna Maria home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story elevated beach home with gorgeous water views, steps from park and two fishing piers. Enjoy meals in the separ ...
From $405 per night (USD)Expedia
From $283 per night (USD)VRBO
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Cabana B by Anna Maria Life Vacation Rentals 301 Poinsettia Rd., Anna Maria, FL 34216 What you'll love about this ...
From $283 per night (USD)VRBO
From $386 per night (USD)Expedia
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Gumbo Cottage located just 7 houses from the Gulf beaches of Anna Maria Island and a street away from downtow ...
From $386 per night (USD)Expedia
From $448 per night (USD)VRBO
Minnie Cottage- Beautiful 3 bedroom heated pool/spa and short walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Minnie Cottage 125 47th Street, Holmes Beach, FL 34217 VRC20-000146 What you will love about this property: • Short stro ...
From $448 per night (USD)VRBO
From $752 per night (USD)Expedia
Boater's Dream! 1/2 Block from Beach- Private Boat Dock & 30' Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the Traffic: Private Waterfront Oasis on AMI’s Historic North End. Welcome to Sunshine Cottage, a beautifull ...
From $752 per night (USD)Expedia
From $276 per night (USD)VRBO
EXCELLENT LOCATION IN THE HEART OF HOLMES BEACH ON ANNA MARIA ISLAND!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Renovated in 2025, bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minu ...
From $276 per night (USD)VRBO
From $584 per night (USD)VRBO
TROPICAL POOL, PRIVACY! ON WATER! BOAT OPTION, PETS ! HUGE AUG/SEPT 2026 DISC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CASA ENCANTADA, THE SECLUDED ESTATE ON THE MANATEE RIVER! ...
From $584 per night (USD)VRBO
From $459 per night (USD)VRBO
Toes in the Water: North End, West of Gulf, Steps to Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Toes in the Water by Anna Maria Life Vacation Rentals 110 Palm Ave, Anna Maria, FL 34216 What You'll Love About This Ho ...
From $459 per night (USD)VRBO
From $814 per night (USD)Expedia
Stunning Luxury Gulf Home, Private Heated Pool/Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Temp Promo: Book 7 nights or more with us by September 30, get a free 6P Bintelli Golf Cart for your stay! Normally $12 ...
From $814 per night (USD)Expedia
From $484 per night (USD)VRBO
Sunkissed by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunkissed is a beautiful elevated townhome that is located in Holmes Beach-just a short stroll to the gorgeous white san ...
From $484 per night (USD)VRBO
From $758 per night (USD)VRBO
NO REGRETS -Bright beautiful sunny home. Elevator beside driveway to upstairs.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and ...
From $758 per night (USD)VRBO
From $411 per night (USD)VRBO
Escape to Paradise–The Beach Club AMI #1 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Beach Club at Anna Maria – Offered by RVA Experience the charm of Old Florida with modern flair at The Beach Club a ...
From $411 per night (USD)VRBO
From $522 per night (USD)Expedia
2BR Gulfside Paradise – Longboat Key by RVA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cabana Beach Club #2 | Gulf-Front Vacation Rental on Longboat Key Experience the beauty of Florida's Gulf Coast at Caba ...
From $522 per night (USD)Expedia
From $557 per night (USD)VRBO
Beach House 3 · Ground Level · Door to Sand
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please note — there is currently some construction taking place at Beach House Resort that is expected to continue throu ...
From $557 per night (USD)VRBO
From $318 per night (USD)Expedia
Cedars East #528 Townhome by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cedars East #528 – Longboat Key Townhome Vacation Rental Escape to island living at Cedars East #528, a spacious 2-bedr ...
From $318 per night (USD)Expedia
From $304 per night (USD)VRBO
Silver Sands Serenity – Unit 234 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Silver Sands Gulf Beach Resort #234 – Garden View Condo with Private Beach Access on Longboat Key Escape to paradise at ...
From $304 per night (USD)VRBO
From $376 per night (USD)Expedia
Coastal Comfort - Beach Castle #23 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in this privately owned, coastal-themed ground-floor condo on Longboat Key, perfect for couples or small families. ...
From $376 per night (USD)Expedia
From $436 per night (USD)VRBO
Silver Sands #245 Resort by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $436 per night (USD)VRBO
From $302 per night (USD)Expedia
Pet Friendly LBK Home-Space Galore w Pool, Fireplace & Walk to Beach by RVA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
RVA presents this spacious vacation home. The Tarawitt Home, is located on a secluded road at the northern tip of Longbo ...
From $302 per night (USD)Expedia
From $213 per night (USD)VRBO
Sea Pirate 7 · Renovated 2026 · Pool · Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000815 2BR · 1BA · Sleeps 4 · 2026 Complete Renovation · Across from Gulf · Heated Pool · Private Fenced Patio · ...
From $213 per night (USD)VRBO
From $391 per night (USD)Expedia
Beachside Bliss #5 Beach Club AMI by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...
From $391 per night (USD)Expedia
From $389 per night (USD)VRBO
Gulf Front Escape – Silver Sands #252 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $389 per night (USD)VRBO
From $512 per night (USD)Expedia
Rooftop Sunsets 2 Bed Unit Beach Club AMI 4 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
RVA features The Beach Club at Anna Maria. Old Florida charm meets modern, designer-decorated decor at this private, un- ...
From $512 per night (USD)Expedia
From $173 per night (USD)VRBO
Island Retreat by SeaBreeze Vacation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds an ...
From $173 per night (USD)VRBO
From $522 per night (USD)Expedia
Relaxing 2BR Retreat-Silver Sands Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $522 per night (USD)Expedia
From $525 per night (USD)VRBO
Beachfront Bliss: Beach Castle #1 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Castle Resort #1 | Gulf-Front 2-Bedroom Vacation Rental on Longboat Key Escape to paradise at Beach Castle Resort ...
From $525 per night (USD)VRBO
From $407 per night (USD)Expedia
Gulfside Getaway – Silver Sands Resort #235 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Silver Sands Gulf Beach Resort #235 by RVA Resort Vacations | Spacious 2-Bedroom Condo on Longboat Key Escape to the tr ...
From $407 per night (USD)Expedia
From $457 per night (USD)VRBO
2BR Gulf View Condo Cabana Beach Club #7 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cabana Beach Club #7 | Luxury Gulf-Front Vacation Rental on Longboat Key Discover the ultimate Longboat Key vacation re ...
From $457 per night (USD)VRBO
From $401 per night (USD)Expedia
Relax, Recharge & Repeat – Silver Sands #241 by RVA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $401 per night (USD)Expedia
From $328 per night (USD)VRBO
Pet-Friendly 2BR Condo–Cedars East #810 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $328 per night (USD)VRBO
From $340 per night (USD)Expedia
Outrigger #8 Condo by RVA Peaceful Gulf
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...
From $340 per night (USD)Expedia