Anna Maria, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anna Maria, Florida on RentalSaver.com!

Anna Maria Rentals

From $1560 per night (USD)
VRBO
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 $1560 per night (USD)
VRBO
From $636 per night (USD)
Expedia
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 $636 per night (USD)
Expedia
From $536 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 $536 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Beautiful 1 Bedroom Condo with Beach Facing Balcony and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #112 by Anna Maria Vacations 100 73rd Street, Unit #112, Holmes Beach, Florida VRC21-000175 Your d ...
From $566 per night (USD)
Expedia
From $557 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) Highlights - Living & Dining Area: Open-concept s ...
From $557 per night (USD)
VRBO
From $542 per night (USD)
Expedia
Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Discover Mango Bay, A Stunning Coastal Home Designed For ...
From $542 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Family Friendly Home with Pool, 4 mins to Beach! - Starfish Cove, B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, B by AMI Locals 7802 Palm Dr, Unit B, Holmes Beach, FL 34217 VRC21-000189 Welcome to Starfish Cove, B, ...
From $199 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Dog-Friendly Home with Pool! 4 mins to the Beach - Starfish Cove, A
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, A by AMI Locals 7802 Palm Dr, Unit A, Holmes Beach, FL 34217 VRC17-000165 Welcome to Starfish Cove, A, ...
From $200 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Flexible Check-in and checkout days —with some exceptions for holidays and certain times of the year—and never on Sunday ...
From $352 per night (USD)
VRBO
From $306 per night (USD)
Expedia
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 $306 per night (USD)
Expedia
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VRBO
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
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VRBO
From $373 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 $373 per night (USD)
Expedia
From $409 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 $409 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with L ...
From $496 per night (USD)
Expedia
From $378 per night (USD)
VRBO
217 84th - Anna Maria Island- Private home 3 Bedroom/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $378 per night (USD)
VRBO
From $1513 per night (USD)
Expedia
Pool*Hot Tub*Tiki Bar*Pickleball Court*Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Modern southern style and comfort await you at Conch Shell: A resort-like property on Bimini Bay. Meandering walkways ta ...
From $1513 per night (USD)
Expedia
From $419 per night (USD)
VRBO
Bay Breeze Cottages #3
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $419 per night (USD)
VRBO
From $617 per night (USD)
Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $617 per night (USD)
Expedia
From $471 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 $471 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $339 per night (USD)
Expedia
From $968 per night (USD)
VRBO
Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool/Spa |
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bimini Bay Breeze is a gorgeous canal front home with an expansive outdoor living area and is conveniently located close ...
From $968 per night (USD)
VRBO
From $691 per night (USD)
Expedia
September Golf Cart Special
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $691 per night (USD)
Expedia
From $1132 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 $1132 per night (USD)
VRBO
From $620 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) Step Into AMI Peppertree Paradise, A Coastal ...
From $620 per night (USD)
Expedia
From $430 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 $430 per night (USD)
VRBO
From $442 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 $442 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $418 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 $418 per night (USD)
Expedia
From $421 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 $421 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Home with Private Outdoor Living Space, Community Pool - Sea La Vie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by AMI Locals Condo in Holmes Beach, Florida VRC21-000203 Welcome to Sea La Vie! This three-bedroom, three- ...
From $336 per night (USD)
Expedia
From $2265 per night (USD)
VRBO
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 $2265 per night (USD)
VRBO
From $326 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 $326 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Sea Spray 2: *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 $319 per night (USD)
VRBO
From $741 per night (USD)
Expedia
North Shore Very Walkable to AMI fun & close to the Beach, Stunning Pool
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 2 ...
From $741 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Seahorse Cottage! Walk to Beach & Shops!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seahorse Cottage by AMI Locals Home in Holmes, Beach Florida VRC16-000110 Enjoy a luxury vacation with friends and fami ...
From $602 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Coconuts Beachfront #109 by AMI Locals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #109 by AMI Locals 100 73rd St Unit 109 - Holmes Beach, FL 34217 Welcome to Coconuts Beachfront # ...
From $321 per night (USD)
Expedia
From $538 per night (USD)
VRBO
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 $538 per night (USD)
VRBO
From $797 per night (USD)
Expedia
Bridgeview: Bay front with sweeping views, sleeps 12!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Relax in this beautiful, bay view home! Bridgeview is the perfect vacation home for large family or multi-family getaway ...
From $797 per night (USD)
Expedia
From $723 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 $723 per night (USD)
VRBO
From $382 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 $382 per night (USD)
Expedia
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VRBO
Amazing Resort Sixty-Six, 1 Bedroom Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For Pricing
VRBO
From $1292 per night (USD)
Expedia
Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
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 $1292 per night (USD)
Expedia
From $541 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 $541 per night (USD)
VRBO
From $690 per night (USD)
Expedia
Sunset at 714 - 4BR/3BA - Anna Maria City - By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Bean Point beach access is a favorite among locals who love surfing and soaking up sun putting “Sunset at 714” in on ...
From $690 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Canary Cottage Perfect modern cottage, quiet street, short walk to the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Canary Cottage has 2 bedrooms and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- Thi ...
From $313 per night (USD)
VRBO
From $1103 per night (USD)
Expedia
Fanta-Sea | Beachfront 4BR Home w/ Pool, Volleyball & Gulf Access
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Fanta-Sea | Private Beachfront Oasis w/ Pool, Volleyball & Gulf Access – 4BR/4BA Escape to Fanta-Sea, a rare ground-l ...
From $1103 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Egret at Blue Lagoon on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $292 per night (USD)
VRBO
From $1447 per night (USD)
Expedia
Dream Luxury Vacation Home with a Guest House, Private Pool, and Bay Views!
Bedrooms:
6
Bathrooms:
8
Sleeps:
18
Blue Bay by Anna Maria Island Accommodations 205 S Bay Blvd, Anna Maria, Florida VPR16-000138 Experience the ultimate ...
From $1447 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Charming Island Escape with Private Pool and Screened Lanai!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Sweet Melissa’s Beach House by AMI Locals 317 N Bay Blvd, Anna Maria, Florida VR19-000057 Welcome to Sweet Melissa’ ...
From $496 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Pete's Blue Heaven: Steps to beach w/heated pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Plan your next island vacation at this exception 4 bedroom, 2 bath home located at the north end of Anna Maria! Enjoy th ...
From $597 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Summer Wind- An island getaway in the perfect location.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $432 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Luxury bungalow with pool and spa! Canal front with dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bamboo Bungalow by AMI Locals Home in Anna Maria VR19-000043 Welcome to the Bamboo Bungalow, a canal-front home where ...
From $426 per night (USD)
Expedia
From $615 per night (USD)
VRBO
Bon Ami: North End AMI, Pool Home, Short Walk to Bean Point by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bon Ami by Anna Maria Life Vacation Rentals 804 North Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: ...
From $615 per night (USD)
VRBO
Click For Pricing
Expedia
Island Time – Coastal Home w/ Lagoon-Style Pool & Spa, Short Walk to Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Island Time! On Anna Maria Island (Holmes Beach, FL) Island Time is a Spacious Coastal Retreat with a Privat ...
Click For Pricing
Expedia
From $275 per night (USD)
VRBO
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cute as a bug bungalow on Anna Maria's lovely north end. A block from City Pier and Tampa Bay and only four blocks to th ...
From $275 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $277 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Anna Cabana A: North End Pool Home, Short Walk To Beach by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Anna Cabana A by Anna Maria Life Vacation Rentals 770 Jacaranda Rd., Anna Maria, FL 34216 What you'll love about this h ...
From $269 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Voted a Tropical paradise perched among native banyon trees. Wake to the sound of sea birds in this tropical paradise. P ...
From $440 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positi ...
From $430 per night (USD)
VRBO
From $412 per night (USD)
Expedia
3 bedroom, on AMI, heated private pool, PET FRIENDLY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The family friendly Florida vacation you need is waiting at Mykonos! This Anna Maria Island beach rental has it all. Fro ...
From $412 per night (USD)
Expedia
From $769 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 $769 per night (USD)
VRBO
From $329 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 $329 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Decked Out – AMI Luxury Retreat w/ Heated Pool In A Prime Island Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Decked Out! On Anna Maria Island (Anna Maria, FL) Discover Decked Out, Where Island Luxury Meets Relaxation ...
From $571 per night (USD)
VRBO
From $274 per night (USD)
Expedia
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 $274 per night (USD)
Expedia
From $240 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 $240 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Aloha Fern: North End Beach House, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Aloha Fern by Anna Maria Life Vacation Rentals 702 Fern, Anna Maria, FL 34216 What You'll Love About This Home: Locatio ...
From $568 per night (USD)
Expedia
From $1538 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 $1538 per night (USD)
VRBO
From $794 per night (USD)
Expedia
Beautiful New Pool Home with Gulf Views and Heated pool, steps to Bean Point!
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 $794 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Dog-friendly seaside home - heated private pool & spa, great location near beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $307 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Harmony House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $310 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Waterfront condo with pool and easy access to sugar sand beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A Gulf Front Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $341 per night (USD)
VRBO
From $315 per night (USD)
Expedia
High-end home w/ heated private pool/spa, courtyard, & floor-to-ceiling windows
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Dream Maker Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $315 per night (USD)
Expedia
From $972 per night (USD)
VRBO
Canalfront Island Gem with Private Heated Pool, Dock, Ping-Pong, & Putting Green
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Mermaid Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $972 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Incredible, spacious home with a private heated pool - close to the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Le Paradis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $504 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Dog-friendly house w/ beautiful upstairs deck and grill, steps from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sandy's Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $329 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Island-style townhome with WiFi & pool - minutes from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
North Beach Village 27 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $537 per night (USD)
Expedia
From $934 per night (USD)
VRBO
Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
3 Oars Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $934 per night (USD)
VRBO
From $569 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 405 Pine Ave, Anna Maria, Florida 34216 Welcome to Buttonwood Cottage, a recently r ...
From $569 per night (USD)
Expedia
From $1364 per night (USD)
VRBO
Luxury Island Retreat: Pool, Spa and Walk to Beach
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
Endless Summer by Anna Maria Island Accommodations 406 Spring Ave, Anna Maria, Florida VR19-000059 Welcome to Endl ...
From $1364 per night (USD)
VRBO
From $446 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 204 71st Street | Holmes Beach, Florida VRC21-000101 Welcome to Pure Beach, a bright and s ...
From $446 per night (USD)
Expedia
From $636 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) *The home is next to a construction site. There is n ...
From $636 per night (USD)
VRBO
From $796 per night (USD)
Expedia
Luxurious Island Retreat with Pool, Spa and Private Suite
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Freckled Fin by AMI Locals 422 Magnolia Ave, Anna Maria, Florida VR19-000006 Welcome to Freckled Fin, a vibrant and ...
From $796 per night (USD)
Expedia
$Beachfront Luxury Hot Tub + Private Cottage\n3 en-suite king + 1BR + golf cart$
From $1294 per night (USD)
VRBO
Beachfront Luxury Hot Tub + Private Cottage\n3 en-suite king + 1BR + golf cart
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Serendipity Gulf – Gulf Front Luxury with Cottage | Anna Maria Island Experience true beachfront living at Serendipity ...
From $1294 per night (USD)
VRBO
From $1823 per night (USD)
Expedia
Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tripletail @ 308 S Bay Blvd – Private Beachfront Luxury Home 4 King Bedrooms | 4 Bathrooms | Heated Pool + Hot Tub | Go ...
From $1823 per night (USD)
Expedia
From $269 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 $269 per night (USD)
VRBO
From $1121 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 $1121 per night (USD)
Expedia
From $654 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 $654 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Starfish Cottage - sleeps 4 guests in 2 bedrooms
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 equ ...
From $431 per night (USD)
Expedia
From $478 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 $478 per night (USD)
VRBO
From $676 per night (USD)
Expedia
Canal - C-View by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Recently renovated, C-View is the perfect island getaway for your family vacation. Conveniently located within walking d ...
From $676 per night (USD)
Expedia
From $1037 per night (USD)
VRBO
BUENA VISTA LUXURY BEACHFRONT 4BR - 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 $1037 per night (USD)
VRBO
From $981 per night (USD)
Expedia
DIRECT BEACH FRONT - Luxury 4BR Condo - Anna Maria Island- By Island Real Estate
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 $981 per night (USD)
Expedia
From $1085 per night (USD)
VRBO
Vitamin Sea managed by Beach Retreats FL Anna Maria Island
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
☀️ Vitamin Sea by Beach Retreats Vacation Rentals 📍 146 Crescent Dr, Anna Maria, FL 34216 Welcome to Vitamin Sea, a st ...
From $1085 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Waterfront home near beaches with private heated pool, spa, and more
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Surrounded By Sea Breezes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $556 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Upscale condo with large deck & shared pool - just steps from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
La Casa Karen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $554 per night (USD)
VRBO
From $1574 per night (USD)
Expedia
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 $1574 per night (USD)
Expedia
From $302 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 $302 per night (USD)
VRBO
From $571 per night (USD)
Expedia
La Cocolia located on north end of AMI. Lagoon Pool, Walk to Pine Ave.
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 $571 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Anna Maria North End Retreat, Private Pool, 250 feet from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The North Shore House is a clean and peaceful cottage, located in the desirable north end of Anna Maria Island, just 250 ...
From $602 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Breezy house with great location near beach, shopping & dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Guava Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $218 per night (USD)
Expedia

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