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From $807 per night (USD)
VRBO
Bella Vista: Bay front with gorgeous views and outdoor living space.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Looking for the perfect waterfront home for your next vacation? Bella Vista is a beautiful Bayfront home with gorgeous v ...
From $807 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Bellablu: A Waterfront Haven, The Ideal Retreat for Your Next Getaway!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to waterfront paradise at Bellablu! This newly renovated haven offers the ideal retreat for your next vacation. W ...
From $661 per night (USD)
Expedia
From $622 per night (USD)
VRBO
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to Paradise by the Bay - The Ultimate Vacation Retreat for Your Family! Uncover your own private paradise at ou ...
From $622 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Aqua Marine By The Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover an Anna Maria little secret --BAYFRONT HOME WITH A WHITE SANDY BEACH -- offering the best of both worlds. Nes ...
From $538 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Peaceful Poolside Escape Near Holmes Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Blue Oasis East by AMI Locals 401 72nd St A, Holmes Beach, FL 34217 VRC21-000102 Welcome to Blue Oasis East, a beaut ...
From $442 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Blue Oasis West! Family-Friendly Duplex Near Shops and Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Blue Oasis West by AMI Locals 401 72nd St B, Holmes Beach, FL VRC21-000103 Welcome to Blue Oasis West, a newly remod ...
From $447 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Waterfront Paradise- Heated pool, AMAZING Sunsets!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Welcome to Paradise! Heated Salt Pool, RIGHT-On-The-Bay! Smart TVs, Strong WiFi, Artfully decorated in an expansive 4,20 ...
From $683 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Paradise in Perico Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perico Bay Club is a world class Resort Style Community with award winning, lush landscaping conveniently located 2 mile ...
From $172 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Amazing bayfront views! Book your tropical escape today and enjoy an amazing getaway! Call today to book your Holiday vacation!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Wake up to the view of paradise in this vividly colored, 2 bedroom/ 2 bathroom, first floor condo located directly water ...
From $254 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Bradenton - Minutes to IMG Academy / Beaches / Heated pool home / CASAMIA
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to CASAMIA 1. Located minutes away from the gorgeous gulf coast beaches, you will enjoy all the amenit ...
From $345 per night (USD)
Expedia
From $356 per night (USD)
VRBO
One Particular Harbour 376-301~ Beaches 5 minutes
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Stunningly decorated two bedroom, two bath condo in Anna Maria Island/Bradenton's most desired vacation resort. You will ...
From $356 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Stunning 3 Bed Home with South Facing Solar Heated Pool at Tara Golf
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Gorgeous 3 bedroom, 3 bathroom solar heated pool home backing on to 1st fairway of Tara Golf Course. If you choose, you ...
From $296 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Castnetter Beach Resort 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protec ...
From $280 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Welcome to paradise!! Please note: Amenities temporarily unavailable due to hurricane repairs.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Come experience the hidden gem of Florida’s Gulf Coast in this comfortable 2 bedroom/ 2 bathroom condo. The king-sized b ...
From $266 per night (USD)
Expedia
From $311 per night (USD)
VRBO
CHARMING VACATION HOME#FREE HEATED POOL#IMG#AMI
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
<p>Close to snorkeling, kayaking, and more, this family-friendly villa brings it all within reach. With convenient cover ...
From $311 per night (USD)
VRBO
From $326 per night (USD)
Expedia
This AMAZING 2/2 has stunning views of the bay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Due to Hurricane Helene, our properties are still recovering and updating until further notice. Harbor Villa Club is no ...
From $326 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Love the beach? Tennis? Swimming? This great family friendly retreat has it all!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Spacious 2400 square foot elevated home (there are 16 steps to enter and exit) featuring wide open floor plan with vault ...
From $355 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Luxury Beach Front Condo on the most private and select beach in Longboat Key!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Are you looking for a quiet and select, non-touristy location right on what happens to be one of the most spectacular an ...
From $278 per night (USD)
VRBO
From $356 per night (USD)
VRBO
DIRECT GULFRONT CONDO - 2BR/2BA Condo with pool and tennis - By Island Real Esta
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please Note: Exterior painting and roofing projects are scheduled between Sept 22–Dec 31, 2025. Work may cause noise or ...
From $356 per night (USD)
VRBO
From $108 per night (USD)
Expedia
3 Bed, 2 Bath Home Away From Home in Resort Style Setting
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Resort style, third floor condo with 3 bedrooms, 2 bathrooms at the Serenata Condominium gated community. Includes: fu ...
From $108 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Spacious Condo on the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly remodeled condo with a view of the gulf from your relaxing balcony. Large heated pool and hot tub amid lush landsc ...
From $306 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bean Point Bungalow by AMI Locals 770 N Shore Dr, Anna Maria, FL VR17-000061 Welcome to Bean Point Bungalow, a char ...
From $476 per night (USD)
Expedia
Click For Pricing
VRBO
2 Bedroom Condo at Lakewood National Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Thanks for visiting our listing. This professionally furnished two year old condo is your comfortable place to relax b ...
Click For Pricing
VRBO
From $318 per night (USD)
Expedia
Bradenton Beach FL, Waterfront Condo, Newly Renovated, 2 bed/2 bath, 2nd Story
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 1,100-square-foot rebuilt and redesigned condominium on gorgeous and quaint Anna Maria Island, offers spectacular v ...
From $318 per night (USD)
Expedia
Click For Pricing
VRBO
Resort Sixty-Six - Anna Maria Island Quiet Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
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
Click For Pricing
Expedia
Via Roma Beach Resort - 1 Bedroom Garden View
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
Expedia
From $235 per night (USD)
VRBO
Spanish Style Home With Private Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Spanish style Single family home in West Bradenton. Bild in 1925 and totally remodeled and updated in 2015. Only 8.9 mil ...
From $235 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Sun and Surf Direct Gulf Front Condo on Anna Maria Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful ...
From $466 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Elevated 3BR/3BA Home - Private Pool Home - By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Newly Updated - New bathrooms and updates completed in February of 2023!! “Forget Me Knot” is a gem among island homes. ...
From $547 per night (USD)
VRBO
From $846 per night (USD)
Expedia
AMI Stay! Family-Friendly Home with Pool, Soaking Tub and Bay Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bay Happy by AMI Locals 403 N Bay Blvd, Anna Maria, FL VR21-000047 Welcome to Bay Happy, a four bedroom, three bath ...
From $846 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Sunshine Villa Minutes from AMI and Robinson Preserve. Pool, Spa, Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Ready to unwind and relax? Welcome to Sunshine Villa a hidden gem just 2 miles from the beaches on Anna Maria Island. T ...
From $336 per night (USD)
VRBO
From $904 per night (USD)
Expedia
Anna Maria Luxury Home with Private Pool, Rooftop Deck & Gulf Views! 1.5 Blocks
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Montego Bay by AMI Locals 211 Magnolia Avenue, Anna Maria, Florida 34216 VPR16-000472 Escape to Montego Bay, a stunnin ...
From $904 per night (USD)
Expedia
From $374 per night (USD)
VRBO
3 bedroom near AMI with private heated pool, pet friendly.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kim's Palm Cottage is a one story 3 bedrooms, 2 baths home with a heated pool in the sought-after Village Green neighbor ...
From $374 per night (USD)
VRBO
From $600 per night (USD)
Expedia
At Last: Ground-level, pool, hot tub, canalfront, dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
***Photos Updated May 2025*** Come slip away to this luxurious island retreat where all of your cares will drift away! T ...
From $600 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Very walkable to the beach and the pool is 50 feet away.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Ground level condo is a 2 minute walk to the inviting soft sands of the Gulf of Mexico on Anna Maria Island and one ...
From $208 per night (USD)
VRBO
From $228 per night (USD)
Expedia
7204-101 Great view Coach home on River Strand with golf membership
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Coast Florida Properties would like to introduce the latest addition to our portfolio of vacation homes. 7204 RIVER ...
From $228 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Appletini- Dog Friendly Private Pool Home IN Heart of Anna Maria By Island Real
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tiki waterfall heated pool with comfortable pool side furniture will melt your worries away. This ground level property ...
From $366 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Shorewalk CF condo 2 Bedroom/ 2 Bath-near Beaches, IMG, Pool, Tennis, Pickleball
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy this beautiful lake view second floor 2 Bedroom/2 Bath condo 5 min away from IMG Academy, 15 min to the Beaches on ...
From $221 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Luxury Villa with Pool, Near Beach!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Villa #7 AMI Lime Fish by AMI Locals 3602 Gulf Dr, Unit #1, Holmes Beach, FL 34217 Welcome to Villa #7 AMI Lime Fish, a ...
From $427 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Unit #212 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tastefully renovated, non-smoking, second floor unit. New updates every year. Light and bright with all the comforts of ...
From $407 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Private Pool! Ping-Pong, Pool Table, Putt-Putt!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stormalong Bay by Stormalong Bay by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Welcome to Stormal ...
From $641 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Anna Maria Island Townhouse - Simply Fabulous! Your Perfect Vacation Location!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This townhouse is beautifully decorated and completely modernized with everything you need for the perfect vacation in p ...
From $355 per night (USD)
Expedia
From $1028 per night (USD)
VRBO
Ultimate Family Retreat with Pool, Waterslide and Rooftop Deck
Bedrooms:
7
Bathrooms:
8
Sleeps:
16
Beach Haven by AMI Locals 5501 Holmes Blvd, Holmes Beach, Florida VRC18-000066 Welcome to Beach Haven, an eight b ...
From $1028 per night (USD)
VRBO
From $515 per night (USD)
Expedia
SeaStarVilla by Duncan Real Estate
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Sea Star Villa! This well constructed 2-bedroom, 3-bathroom Island home with a bonus room is ready to host gu ...
From $515 per night (USD)
Expedia
From $472 per night (USD)
VRBO
4Bd 4Ba private, 4 kings bf, heated pool, sleeps 16+!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
This spacious home boasts 2422 square-feet of luxurious one level floor. Completely remodeled home, high end finishes su ...
From $472 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Shell Game: Playa Encantada - Beachfront Community Steps to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shell Game has recently been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious ...
From $270 per night (USD)
VRBO
From $386 per night (USD)
VRBO
Cozy Cabana East – AMI w/ Heated Pool, Pets & Walk To The Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Cozy Cabana East! On Anna Maria Island (Holmes Beach, Florida) Discover Cozy Cabana East, Where Island Comfo ...
From $386 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Beachfront Condo with Stunning Gulf Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Paradise #4 by AMI Locals Condo in Holmes Beach, Florida VRC21-000114 Welcome to Island Paradise #4, a two-bed ...
From $453 per night (USD)
Expedia
From $710 per night (USD)
VRBO
Beachfront Condo! Gulf Views, Pool, and Balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Paradise #6 by AMI Locals 3708 Gulf Dr, Unit #6, Holmes Beach, FL 34217 VRC22-000085 Welcome to Island Paradise ...
From $710 per night (USD)
VRBO
From $1025 per night (USD)
Expedia
Tropical Backyard Escape with Pool, Hot Tub, and Waterslide
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Conch House by AMI Locals 307 66th St, Unit B | Holmes Beach, Florida VRC18-000085 Welcome to Conch House, a gorge ...
From $1025 per night (USD)
Expedia
From $1347 per night (USD)
VRBO
Beachfront Bliss! Pool, Spa & Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beachfront Bungalow by AMI Locals Holmes Beach Gulf-Front Cottage with Private Pool and Spa VRC19-000270 Welcome to ...
From $1347 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Unit #207 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Second floor,.. It's very cozy with all the comforts of home. This renovated unit has an updated kitchen and baths wit ...
From $418 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Saltwater Pool, Spa & Lanai: Bradenton Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
- Lake Views - Community Amenities Treat your family to the perfect FL getaway at this vacation rental in Bradenton! Th ...
From $414 per night (USD)
VRBO
From $811 per night (USD)
Expedia
Dog friendly home near the Gulf!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Coast is Clear by AMI Locals Home in Anna Maria, Florida VR22-000035 Welcome to Coast is Clear, a refreshing beach home ...
From $811 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Newly Renovated - 1 Block from the Beach, Walk to Bars, Restaurants & Shopping!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**NON-SMOKING PROPERTY** The Haven at Bay Watch is newly renovated … everything from the walls in is brand new. The Hav ...
From $357 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Beach Condo with Pool Near Holmes Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Poolside #104 by AMI Locals 100 73rd St, Unit #104, Holmes Beach, FL 34217 VRC16-000664 Welcome to Coconuts ...
From $430 per night (USD)
Expedia
From $2512 per night (USD)
VRBO
Beachfront - New Listing!
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
The Diamond Star Beach House ***Brand New 2025 Remodel*** Welcome to The Diamond Star! Experience beachfront living ...
From $2512 per night (USD)
VRBO
From $2362 per night (USD)
Expedia
Luxury Beachfront Home with Pool, Golf Cart and Bikes Included!
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Beachfront Paradise by AMI Locals 2514 Gulf Drive North, Bradenton Beach, Florida Escape to Beachfront Paradise, an ...
From $2362 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Completely remodeled beach front condo with full ocean views, steps to the water
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Completely remodeled gulf front condo located on beautiful Anna Maria Island. 180 degree views of ocean from Living roo ...
From $413 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Sleeps 12!! Spacious Retreat in Sarasota, Close to Beaches and Downtown
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
Get into VACATION MODE at Paradise Palms! Bring the whole family to this beach inspired, well appointed home with lots ...
From $362 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Private Pool/Spa - A Wave From It All by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New Name - A Wave From It All, formerly known as Island Dream, is a recently updated custom home nestled in the quiet re ...
From $370 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Sul Mare at Vista Grande on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
By far the BEST direct view of the Gulf you will find on Anna Maria Island. Exclusive SUL MARE with floor to ceiling win ...
From $669 per night (USD)
Expedia
From $909 per night (USD)
VRBO
Luxury home with AMAZING backyard Pool and Spa! So close to beach and shopping!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Daiquiri Deck by AMI Locals Home in Anna Maria, Florida VR18-000093 Welcome to Daiquiri Deck, a stunning four-bedroom a ...
From $909 per night (USD)
VRBO
From $1380 per night (USD)
Expedia
Beautiful Home with Pool, Waterslide and Spa! Gulf and Bay Views, Rooftop Deck -
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
Ocean Breeze by AMI Locals 106 7th Street S, Bradenton Beach, Florida 34217 TPL21-000100 Experience the ultimate vacat ...
From $1380 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Shorewalk CK condo 2 Bedroom/ 2 Bath-near Beaches, IMG, Pool, Tennis, Pickleball
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy this beautiful lake view first floor 2 Bedroom/2 Bath condo 5 min away from IMG Academy, 15 min to the Beaches on ...
From $208 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Panoramic bay views! 3-minute walk to beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
What a gem of a spot to spend your Anna Maria Island vacation! This lovely two bedroom, two bath condo is directly bayfr ...
From $388 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Anna Maria Island condo with heated pool, short walk from the beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sea Pirate 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $368 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BRAND NEW POOL! Located on the coveted northern end of Anna Maria Island, “Maria's Way” is a charming beach cottage off ...
From $397 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Stunning 2/2 Condo LBK with Bay Views & Boat Slip Rental!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Longboat Key is perfect for a dream vacation on an island! This condo offers a stunning 180-degree view of Sarasota Bay. ...
From $457 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
One block off Pine Ave w/ Amazing Rooftop Views! - AMI Memories
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
AMI Memories by AMI Locals Home in Anna Maria VR20-000052 Welcome to AMI Memories! This three-level home boasts fiv ...
From $1102 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Sweet duplex with WiFi, central AC, & gas grill - close to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coastal Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $167 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Lazy Lizard! A Newly Renovated Island Cottage, Close to the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Photos Updated January 2025! LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the night ...
From $215 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Blue Bayou | Family fun pool home with hot tub, canalfront with a dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
From $703 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Paradise Villa- near beautiful beaches and IMG
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come relax in Paradise! The bright, beachy 3/2 home has everything you need for the perfect getaway. Each room has a Sma ...
From $200 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Pink Flamingo in Palm Isle Village - 2BR Condo with Pool - By Island Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Current construction on the premises, may hear construction noise 7am-7pm* Discover the best Anna Maria Island has to ...
From $273 per night (USD)
VRBO
From $781 per night (USD)
Expedia
North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom o ...
From $781 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Colorful Beach Cottage with Heated Pool and Walk to Sand!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Peacock Crossing by AMI Locals 205 Peacock Ln, Unit B | Holmes Beach, Florida VRC22-000116 Welcome to Peacock Cross ...
From $416 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Charming cottage in quiet area, close to beach & bay.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in t ...
From $298 per night (USD)
Expedia
From $1564 per night (USD)
VRBO
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Set on 2 acres of land on a 38 acre private island, this award winning home will provide an island vacation experience f ...
From $1564 per night (USD)
VRBO
From $234 per night (USD)
Expedia
2 Bedroom 2 Bath Luxury Condo in Margaritaville
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This new 2 bedroom 2 bath condo offers a partial courtyard view and spacious accommodations. The 1,500 sq. foot, open la ...
From $234 per night (USD)
Expedia
From $655 per night (USD)
VRBO
Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool h ...
From $655 per night (USD)
VRBO
From $902 per night (USD)
Expedia
4 Bedroom Townhouse - Your private Holmes Beach vacation home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to the spacious Unit 12, a four-bedroom, three-bathroom townhouse attractively adorned with white walls, cool pa ...
From $902 per night (USD)
Expedia
From $334 per night (USD)
VRBO
AMI Moana Villa 3-minute walk to the beach plus community heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Find everything you need for a fun and memorable beach getaway at this three-bedroom Holmes Beach rental! You'll have a ...
From $334 per night (USD)
VRBO
From $1529 per night (USD)
Expedia
Summer Sunset-6 bedroom luxury with private pool directly across from the beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
At A Glance Located across the street from the beach Rooftop deck with Gulf and Bay views Private heated pool Covered l ...
From $1529 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Pine Bay Forest 7521 - Bradenton - Very nice 2 Bedroom /2 Bath villa ,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Pine Bay Forest 7521 - Bradenton - Very nice 2 Bedroom /2 Bath villa, maximum occupancy of 4 people. This very n ...
From $171 per night (USD)
VRBO
From $565 per night (USD)
Expedia
Dreamscape: North End Pool Home, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dreamscape by Anna Maria Life Vacation Rentals 773 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $565 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
5 O'Clock Somewhere by Anna Maria Life Vacation Rentals 216 Chilson, Anna Maria, FL 34216 What You'll Love About This H ...
From $1036 per night (USD)
VRBO
From $1376 per night (USD)
Expedia
Malibu Beach! 8BR Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
Bedrooms:
7
Bathrooms:
8
Sleeps:
16
Malibu Beach by AMI Locals 302 55th St, Holmes Beach, FL VRC18-000067 Welcome to Malibu Beach, an eight bedroom, se ...
From $1376 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Beautiful Cottage with Private Pool, Great Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconut Cottage #1 by AMI Locals Condo in Holmes Beach, FL VRC18-000069 Highlights • 1-minute walk from the Beach • Priv ...
From $293 per night (USD)
VRBO
From $1434 per night (USD)
Expedia
AMI Escape! 6 King Suites, Bunk Rooms and Game Zone Near Holmes Beach
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Surf View by AMI Locals 209 54th St, Holmes Beach, FL VRC18-000095 Welcome to Surf View, an expansive eight bedroom ...
From $1434 per night (USD)
Expedia
From $461 per night (USD)
VRBO
One Particular Harbour 392-102~ Beaches 5 minutes
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Gorgeous three bedroom, three bath unit overlooking the Anna Maria Sound and Intracoastal Waterway. Anna Maria is just a ...
From $461 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Beach N Bay 204 by Duncan Real Estate
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Beach N Bay 204! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your ch ...
From $304 per night (USD)
Expedia
From $211 per night (USD)
VRBO
4330 lakeview updated ground floor unit close to beach and IMG
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious self catering apartment/condo available at the popular resort of Shorewalk Vacation Villas, Bradenton/Sarasota, ...
From $211 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Very Close To IMG Academy, Beaches, Restaurants, Shopping and Grocery Stores.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Cozy two bedrooms and two baths first floor easy access, centrally located, quite, clean corner unit. Recently Updates i ...
From $196 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Home 5 Mins to Beach with Private Pool & Pool Table - Three Little Birds Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Three Little Birds Cottage by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Welcome to Three Littl ...
From $345 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Beautiful Beach Home Right Near the Water with Private Pool, AC, & Fast WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Joy Abounds Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $390 per night (USD)
Expedia
From $992 per night (USD)
VRBO
Sarasota Waterfront - Boat Dock poo/spa, kayaks -12 min to Lido Beach & Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Canal front home with salt system pool/spa, boat & jet ski , kayak lifts. Bring your boat or rent one. Try our 3 kayak ...
From $992 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Heated Pool Florida Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your home away from home in sunny Bradenton, FL! This beautifully furnished 3-bedroom, 2-bathroom heated pool ...
From $363 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Tropical Paradise - boutique house and cottage with outdoor entertainment deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This house, located in a prime location next door to the best restaurant on the Island, is a tropical paradise that you ...
From $589 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Outdoor Bar & Heated Pool: Bradenton Beach Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Treat yourself to a tropical escape while staying at this bright and spacious 2-bed, 2-bath home in Bradenton Beach. Wit ...
From $444 per night (USD)
VRBO

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