Manatee Area Rentals
- From $581 per night (USD)
VRBO
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
- Bedrooms:
- 3
- 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 $581 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Salty Harbor AMI pool retreat near the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our charming Salty Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immedi ...
From $292 per night (USD)Expedia
- From $1235 per night (USD)
VRBO
Gorgeous Waterfront Luxury Home, with Pool, Spa, Rooftop, short walk to beach!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 15
Bayfront Retreat by AMI Locals Home in Bradenton Beach, Florida TPL18-000550 Welcome to Bayfront Retreat, a boater's ...
From $1235 per night (USD)VRBO
- From $280 per night (USD)
Expedia
The Sea is Calling - 3 BR 2 Bath Home with Heated Pool Close to Many Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This stunning 3 bedroom 2 bathroom heated pool home comfortably sleeps 8 and is located in a cul de sac in the well est ...
From $280 per night (USD)Expedia
- From $714 per night (USD)
VRBO
Gorgeous Villa at Islands West Resort! Shared pool, close to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa #1 Sailfish by AMI Locals Villa in Holmes Beach, FL 34217 Welcome to Villa #1 Sailfish, an adorable two-bedroom a ...
From $714 per night (USD)VRBO
- From $386 per night (USD)
Expedia
Beach view. Year-round Balcony Sunsets. Just renovated.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our resort was not affected by the hurricane. We are open for business. We have one more Gulf View unit 403 in this res ...
From $386 per night (USD)Expedia
- From $438 per night (USD)
VRBO
Luxury House, Bradenton, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This new construction home is ready for you to vacation! We all know its all about LOCATION, well this home is located s ...
From $438 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Resort-Style Living at Lovely Lakewood - Heated Pool, Tennis, Golf Membership, Fitness Center & Spa!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 6 Master bedroom – One King bed with Large Smart TV, en-suite bathroom, l ...
From $358 per night (USD)Expedia
- From $481 per night (USD)
VRBO
Luxury House, Bradenton, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This new construction home is ready for you to vacation! We all know its all about LOCATION, well this home is located s ...
From $481 per night (USD)VRBO
- From $502 per night (USD)
Expedia
3 bedroom, on Anna Maria Island, 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 $502 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor NO HURRICANE DAMAGE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private Beach Cottage with apartment on second floor. Top floor apartment has two bedrooms, one bath, Living Room and Ea ...
From $186 per night (USD)VRBO
- From $208 per night (USD)
Expedia
BK-near Beaches and IMG, Pool, Tennis, Pickleball
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this beautiful lake view upstairs 2 Bedroom/2 Bath condo 5 min away from IMG Academy, 15 min to the Beaches on Ann ...
From $208 per night (USD)Expedia
- From $892 per night (USD)
VRBO
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $892 per night (USD)VRBO
- From $332 per night (USD)
Expedia
3 bedroom home on Anna Maria Island, great location, pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summer, season, or in between - this 3 bedroom, 3 bath home is your island retreat. Located in a quiet residential neigh ...
From $332 per night (USD)Expedia
- From $352 per night (USD)
VRBO
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
- Bedrooms:
- 2
- 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 $352 per night (USD)VRBO
- From $391 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 $391 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $311 per night (USD)VRBO
- Click For Pricing
Expedia
Barefoot Bungalow:Dog Friendly, Screened Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Barefoot Bungalow by Anna Maria Life Vacation Rentals 213 70th St., Holmes Beach, FL 34217 What You'll Love About This ...
Click For PricingExpedia
- From $544 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 $544 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Cedars East #603 Townhome by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...
From $268 per night (USD)Expedia
- From $408 per night (USD)
VRBO
Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spectacular Saltwater Seas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $408 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Convenient cottage with pool - easy access to trolley stops & the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunfish 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $349 per night (USD)Expedia
- From $611 per night (USD)
VRBO
Old Florida-style cottage w\/ private heated pool - walk to the beach - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mangrove Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $611 per night (USD)VRBO
- From $401 per night (USD)
Expedia
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 $401 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Dog-friendly cottage w\/ island views, shared pool & private patio - beach nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Starfish Beach Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $300 per night (USD)VRBO
- From $429 per night (USD)
Expedia
Welcoming condo with pool, Gulf views & great location - walk to the beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Palm Isle Village 3208 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $429 per night (USD)Expedia
- From $1118 per night (USD)
VRBO
Luxury beachside home with heated private pool - tranquil & close to everything
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Wine Down Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1118 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Beautiful cottage w\/ heated private pool - walk to beach, dining, Bayfront Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Harmony House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $360 per night (USD)Expedia
- From $678 per night (USD)
VRBO
Historic beach cottage with private pool - walk 1 block to beach & free trolley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Palm Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $678 per night (USD)VRBO
- From $745 per night (USD)
Expedia
Oceanview getaway with pool & private patio - steps from the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Gables 106 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $745 per night (USD)Expedia
- From $673 per night (USD)
VRBO
Beautiful, well-maintained home w\/ heated private pool - walk to beach & dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sundance Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $673 per night (USD)VRBO
- From $279 per night (USD)
Expedia
Waterfront condo with pool and easy access to sugar sand beach
- Bedrooms:
- 2
- 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 $279 per night (USD)Expedia
- Click For Pricing
VRBO
Brand new dog-friendly home w\/ heated private pool in prime locale
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Sunset Glow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For PricingVRBO
- From $501 per night (USD)
Expedia
Waterfront condo with furnished balcony overlooking the pristine beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Shores 205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $501 per night (USD)Expedia
- From $709 per night (USD)
VRBO
High-end home w\/ heated private pool\/spa, courtyard, & floor-to-ceiling windows
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Dream Maker Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $709 per night (USD)VRBO
- From $432 per night (USD)
Expedia
Oceanfront condo with WiFi, heated pool & ocean views, walk to free trolley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Terrace 206 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $432 per night (USD)Expedia
- From $818 per night (USD)
VRBO
Darling beachside villa w\/ space & privacy - a cozy coastal florida experience
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Playa Casanas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $818 per night (USD)VRBO
- From $531 per night (USD)
Expedia
Modern home near Gulf beaches with private heated pool & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Neolinda 305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $531 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Charming condo with heated pool - near beach, wetlands, & trolley stop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sandy Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $241 per night (USD)VRBO
- From $260 per night (USD)
Expedia
Ocean-front condo with WiFi, pool & Gulf views - steps to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Martinique 401S Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $260 per night (USD)Expedia
- From $302 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 $302 per night (USD)VRBO
- From $1102 per night (USD)
Expedia
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 $1102 per night (USD)Expedia
- From $203 per night (USD)
VRBO
Delightful condo with pool, two lanais - walk to beach, dining, shopping
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach View 5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $203 per night (USD)VRBO
- From $229 per night (USD)
Expedia
Bright open-concept condo with pool - near beach, restaurants, & pier
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bay View Inn 202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $229 per night (USD)Expedia
- From $402 per night (USD)
VRBO
Tropical-themed getaway w\/ heated private pool - walk to free trolley, shopping
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $402 per night (USD)VRBO
- From $509 per night (USD)
Expedia
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria's Finest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $509 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Hidden Cove Unit 6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $435 per night (USD)VRBO
- From $409 per night (USD)
Expedia
Gulf-front home with deck and direct beach access - steps to trolley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sea La Vie Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $409 per night (USD)Expedia
- From $343 per night (USD)
VRBO
Waterfront condo w\/ WiFi, furnished balcony and easy beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Anna Maria Island Club Unit 17S Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $343 per night (USD)VRBO
- From $795 per night (USD)
Expedia
Spacious dog-friendly home w\/ heated private pool, a few blocks from the beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Almost Gulf Front Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $795 per night (USD)Expedia
- From $607 per night (USD)
VRBO
Charming gulf-front home right on the beach - stunning views, dogs welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dolphin Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $607 per night (USD)VRBO
- From $343 per night (USD)
Expedia
Comfortable island villa with private heated pool, courtyard & easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Wave Villa East Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $343 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Incredible, spacious home with a private heated pool - close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Le Paradis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $338 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Decked Out - Ready for Thanksgiving, No Damage! Huge Sunny Resort Style Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Decked Out! On Anna Maria Island (Anna Maria, FL) A gorgeous home filled with luxurious furnishings, high-en ...
From $650 per night (USD)Expedia
- From $234 per night (USD)
VRBO
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 $234 per night (USD)VRBO
- From $701 per night (USD)
Expedia
Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
NOTE: the pool and elevator at this property are currently not available. Imagine waking up every morning to a million ...
From $701 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Resort Life Lakewood National - 2 Golf Courses, Tennis, Spa, Pickelball more!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ask about shorter rentals and an option to not use the amenities. Enjoy our newer fully furnished “Palmer’s Cove” cond ...
From $201 per night (USD)VRBO
- Click For Pricing
Expedia
SummerStay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Comfy 2nd floor, 2-bdrm/2-bath condo in quiet, mostly-senior community. Condo has spacious LR/DR and kitchen with lots o ...
Click For PricingExpedia
- From $154 per night (USD)
VRBO
Arbomar 302 Gulf Front 2 BR by FVC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay directly on the beach in this ideal beach getaway located mid-island. The Gulf and sunset views are fantastic and ...
From $154 per night (USD)VRBO
- From $152 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 $152 per night (USD)Expedia
- From $767 per night (USD)
VRBO
Canalfront home w\/ WiFi, heated pool, dock & lanai - 2 blocks to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Heavenly Holly Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $767 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Conveniently located home with WiFi & pool - near beach, dining, shopping
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Cove West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $273 per night (USD)Expedia
- From $326 per night (USD)
VRBO
Adorable condo with a full kitchen & outdoor space - just steps from the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf View Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $326 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Island-style townhome with WiFi & pool - minutes from the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
North Beach Village 27 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $419 per night (USD)Expedia
- From $613 per night (USD)
VRBO
Breezy canalfront home w\/ heated pool & dock - 3 blocks to Bean Point Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Paradise Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $613 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Romantic getaway with WiFi, pool & tennis courts, 2 blocks to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Runaway Bay 256 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $198 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
3 Oars Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dat ...
From $483 per night (USD)VRBO
- From $499 per night (USD)
Expedia
Beautiful San Remo Canal Front Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
San Remo Retreat has been completely and lovingly renovated from top to bottom in 2017 and is gorgeously decorated and m ...
From $499 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Unit #208 Sand Cay Beach Resort Pool and Garden 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 $429 per night (USD)VRBO
- From $655 per night (USD)
Expedia
5 miles from Anna Maria IslandI! Heated pool! Game room and HUGE private yard!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Privacy abounds in this beautiful modern home located in an upscale quiet neighborhood. Enjoy spending time with family ...
From $655 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Adorable Cottage with Heated Pool - Fantastic Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Buttonwood Cottage by AMI Locals Home in Anna Maria, Florida Full of old Florida charm and recently restored, we welcom ...
From $534 per night (USD)VRBO
- From $1113 per night (USD)
Expedia
Beachfront Home with Private Beach Access Near Restaurants & Shops - Happy Ours
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Happy Ours by AMI Locals Home in Anna Maria, FL Welcome to Happy Ours! This spacious beachfront home on Anna Maria Isla ...
From $1113 per night (USD)Expedia
- From $229 per night (USD)
VRBO
Bayview Condo A - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath bay view,...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bayview Condo, Unit A - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Community Pool - Bay ...
From $229 per night (USD)VRBO
- From $1299 per night (USD)
Expedia
Enjoy \"Endless Summer\" at this awesome luxury beach house with your family!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Endless Summer by Anna Maria Island Locals Home in Anna Maria, FL Just one street over from Pine Ave Highlights: - Bea ...
From $1299 per night (USD)Expedia
- From $825 per night (USD)
VRBO
Home near the Beach. SUP Paddleboards, Large Private Pool - Pure Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Pure Beach by Anna Maria Island Locals Home in Holmes Beach, FL VRC21-000101 Welcome to Pure Beach, a luxurious three- ...
From $825 per night (USD)VRBO
- From $814 per night (USD)
Expedia
Point's Hideaway - Ready for Guests, January 2025!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Point's Hideaway! On Anna Maria Island (Anna Maria, FL) HIGHLIGHTS: - Kitchen, Dining, Living w/ TV - 1 King ...
From $814 per night (USD)Expedia
- From $486 per night (USD)
VRBO
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 $486 per night (USD)VRBO
- From $2088 per night (USD)
Expedia
Beaches and Dreams: Ultimate Luxury Beachfront Paradise
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams, where stunning panoramic bay view ...
From $2088 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Island villa with heated private pool, tranquil courtyard, easy beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Wave Villa West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $313 per night (USD)VRBO
- From $688 per night (USD)
Expedia
Stylish & relaxing villa with heated pool - blocks from the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Turtle Cove East and West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $688 per night (USD)Expedia
- From $564 per night (USD)
VRBO
Canal-front home with private dock, covered lanai with heated pool and grill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Coconut Tree Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $564 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
West Bay Point 12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $166 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Dog-friendly house w\/ heated private lagoon pool - two blocks from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LaRaya Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $595 per night (USD)VRBO
- From $497 per night (USD)
Expedia
Dog-friendly house with heated private pool, island views & nearby beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shell House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $497 per night (USD)Expedia
- From $141 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 $141 per night (USD)VRBO
- From $1152 per night (USD)
Expedia
Luxury home, close to the beach! Pool and Spa, great for families!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Freckled Fin by AMI Locals Home in Anna Maria, Florida VR19-000006 Welcome to Freckled Fin, a fun and luxurious vacati ...
From $1152 per night (USD)Expedia
- From $1090 per night (USD)
VRBO
Serendipity Gulfront- gulf beach front
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell sear ...
From $1090 per night (USD)VRBO
- From $1082 per night (USD)
Expedia
Water views- 4 bedroom\/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sky by Serendipity is a unique, elevated island home with 4 bedrooms and 2 bathrooms. Conveniently located on the north ...
From $1082 per night (USD)Expedia
- From $1278 per night (USD)
VRBO
TripleTail- beachfront 4\/4
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 4 bath Beach Front Home with Panoramic views of the Ocean and Skyway Bridge. Watch dolphins swim and play in y ...
From $1278 per night (USD)VRBO
- From $321 per night (USD)
Expedia
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 $321 per night (USD)Expedia
- From $879 per night (USD)
VRBO
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
- Bedrooms:
- 6
- 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 $879 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
NO HURRICANE HELENE AND MILTON DAMAGES! BEACH IS OPEN. POOL IS CLEANED, UP AND RUNNING. GROUND AREA IS CLEANED. WE ARE ...
From $377 per night (USD)Expedia
- From $335 per night (USD)
VRBO
AMAZING BAY FRONT VIEWS! 2\/2 IN RUNAWAY BAY! ANY DAY CHECK-INS AVAILABLE, FALL DATES STILL OPEN!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Want to watch a surreal sunrise over the Bay of Anna Maria Island from bed? Or, take a short walk across the street in t ...
From $335 per night (USD)VRBO
- From $679 per night (USD)
Expedia
Experience Family Fun at Shore Bet: Pool, Games & Dock with Upgrades Coming!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Shore Bet by AMI Locals Home in Anna Maria, Florida VR21-000037 Welcome to Shore Bet, a beautiful canal-front vacatio ...
From $679 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Seaside family-friendly condo with WiFi, pool & prime location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Serenity Now Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $234 per night (USD)VRBO
- From $671 per night (USD)
Expedia
Waterfront Bradenton Home: Heated Pool & Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Book this Bradenton beauty with unbeatable amenities for your next trip! Shrouded in the secrecy of mangrove trees, the ...
From $671 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Holmes Beach Family Home: Private Pool & 3 Decks!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Explore Florida’s beautiful Anna Maria Island from ‘Salty Dogs Beach House,’ a 3-bedroom, 2.5-bathroom, single family Ho ...
From $334 per night (USD)VRBO
- From $217 per night (USD)
Expedia
Inviting Coastal Getaway w\/ Easy Beach Access, Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $217 per night (USD)Expedia
- From $1370 per night (USD)
VRBO
Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach
- Bedrooms:
- 5
- 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 $1370 per night (USD)VRBO
- From $402 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 $402 per night (USD)Expedia