Rental Homes

Choose from one of our gorgeous luxury family homes, from 2 bedrooms to 6 bedrooms, each with their own private backyard and/or pool and in a unique location on the island

La Buena Vida

La Buena Vida

La Buena Vida 3 Bedroom  |  4-7 Night MinimumOverview Updated Waterfront Home w/Heated Pool and Spa on Quiet Street on North End of Island, Easy Walk to Beach 3 Bedroom, 2 Bath in Anna Maria, FL (Anna Maria Island) 1897 sq. ftHighlights Kitchen, Dining Area, Living w/...

Oasis on Spring

Oasis on Spring

Oasis on Spring 4 Bedroom  |  4-7 Night Minimum | Sleeps 8Overview Luxurious Updated Main Home Plus Secondary Guest Home w/Oversized Heated Pool & Spa in True Backyard Oasis 4 Bedroom, 3 Bath in Anna Maria, FL (Anna Maria Island) 1518 sq. ft Highlights Two homes...

Sunset Margarita

Sunset Margarita

Sunset Margarita 2 Bedroom  |  Sleeps 6Overview Luxury Condominium with Screened Lanai, Shared Heated Pool in One Particular Harbour 2 Bedroom, 2 Bath in Bradenton, FL 391 Aruba Circle #301 Less than 2 miles from the Anna Maria Public Beach in the highly desirable...

AMI Peppertree Paradise

AMI Peppertree Paradise

AMI Peppertree Paradise 3 Bedroom  |  4-7 Night MinimumOverview Elevated Updated Home w/Large Heated Pool on Amazing Street on North End of Island, Just 2 Houses to Beach! 3 Bedroom, 2 Bath in Anna Maria, FL (Anna Maria Island) 1970 sq. ft Highlights Kitchen, Dining...

Bodacious Oasis

Bodacious Oasis

Bodacious Oasis 4 Bedroom  |  Sleeps 8Overview Elevated Upscale Spacious Home w/Large Heated Pool & Sunshelf, Steps to Pine Avenue! 4 Bedroom, 2 1/2 Bath in Anna Maria, FL (Anna Maria Island) 2120 sq. feetHighlights Kitchen, Dining Area, Living w/ TV 1 King...

Island Time

Island Time

Island Time 3 Bedroom  |  Sleeps 6Overview Ground Level Spacious Home w/Lagoon Style Enclosed Heated Pool & Spa with Boat Dock Access! 3 Bedroom, 2 Bath in Holmes Beach, FL (Anna Maria Island) 2600 sq. feet Under new ownership & management!Highlights Kitchen,...

Coconut Lagoon

Coconut Lagoon

Coconut Lagoon 3 Bedroom  |  3-7 NightsOverview Ground Level Completely Updated Luxury Historic Home 3 Bed, 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beaches 3 Bedroom, 2 1/2 Bath in Anna Maria, FL 1146 sq. feet Highlights Kitchen,...

A Shore Thing

A Shore Thing

A Shore Thing 4 Bedroom  |  4-7 Night MinimumOverview Newly Constructed Waterfront Home with Pool, Spa, Private Dock on Canal & Gulf & Bay Rooftop Views 4 Bedroom, 5 Full & 2 1/2 Bath in Anna Maria, FL 108 Tern Drive Anna Maria, FL 34216 3875 sq. ft....

Beachy Villa Vista

Beachy Villa Vista

Beachy Villa Vista 5 Bedroom  |  Sleeps 10Overview Single Family Vacation Home with Heated Pool, Spa,  & Deck with GULF VIEWs JUST 3 HOUSES DOWN FROM BEACH 5 Bedroom, 4 1/2 Bath in Anna Maria, FL 2177 sq ft. Highlights Layout       Open layout and spacious...

She’s Always Right

She’s Always Right

She's Always Right 4 - 5 Bedroom  |  Sleeps 8  |  7 Night Minimum Overview New Construction Custom Built Elevated Two-Story Single Family Home with Saltwater Pool & Spa and 1 Block to Beach 204 54th Street 4-5 Bedroom, 4 Bath in Holmes Beach, FL  2112 sq. ft.​...

Sea Glass on Park

Sea Glass on Park

Sea Glass on Park 4 Bedroom  |  Sleeps 9Overview New Construction Stunning Luxury Home, Just Steps to Beach! 4 Bedroom, 3 1/2 Bath in Anna Maria, FL 2350 sq. feetHighlights Open Concept Kitchen, Dining Area, Living w/ TV 1 King Bedroom 1 King Bedroom 1 Queen Bedroom 3...

Bateman’s

Bateman’s

Bateman's 4 Bedroom  |  Sleeps 8  |  4- 7 Night MinimumOverview Newly Constructed Single Family Waterfront Home with Pool & Spa on Canal 4 Bedroom, 4 1/2 Bath in Anna Maria, FL 108 Gull Drive Anna Maria, FL 34216 2543 sq. ft. Highlights Layout  Open layout and...

Sea La Vie Beach House

Sea La Vie Beach House

Sea La Vie Beach House 4 Bedroom  |  Sleeps 8  |  7 Night Minimum Overview Newly Constructed Single Family Waterfront Home with Pool & Spa on Deepwater Canal 4 Bedroom, 4 1/2 Bath in Anna Maria, FL 523 Kumquat Drive Anna Maria, FL 34216 2825 sq. ft.Highlights...

Sea Life Happy

Sea Life Happy

Sea Life Happy 4 Bedroom  |  Sleeps 8Overview Sprawling Canal-front Home with Private Heated Pool & Spa, Dock, Indoor/Outdoor Bar  4 Bedroom, 3 Bath in Anna Maria, FL Sea Life Happy Anna Maria, FL 34216Highlights Open Layout Kitchen, Dining Area, Living Room w/ TV...

Casa Mariposa

Casa Mariposa

Casa Mariposa 4 Bedroom  |  Sleeps 8  |  7 Night Minimum Overview Single Family Home with Pool, Spa, Pool Cabana, Lanais, & Butterfly Sanctuary 4 Bedroom, 4 Bath in Anna Maria, FL Highlights Layout    Open layout and spacious Kitchen, Dining seating 8, Living w/...

Seaswept Mermaid

Seaswept Mermaid

Seaswept Mermaid 4 Bedroom  |  3 BathOverview NEWLY LUXURIOUSLY RENOVATED with Heated Pool, Spa, Bay & Canal Views on Canal with Dock 4 Bedroom, 3 Bath on Anna Maria, FL Seaswept Mermaid Anna Maria, FL 34216 Need more room? Can be rented in conjunction with the...

Salty Pirate

Salty Pirate

Salty Pirate 4 Bedroom  |  3 BathOverview NEWLY LUXURIOUSLY RENOVATED with Heated Pool, Spa, Bay & Canal Views on Canal 4 Bedroom, 3 Bath on Anna Maria, FL Salty Pirate Anna Maria, FL 34216 2512 sq. ft. Need more room? Can be rented in conjunction with the next...

Blue Haven Beach House

Blue Haven Beach House

Blue Haven Beach House 3 Bedroom  |  Sleeps 6Overview Lovely Updated Island Home with Screened-in Lanais and Private Heated Pool, Elevator, Foosball, Ping-Pong, Less than 4 minute Walk to Beach w/ Peek-A-Boo Gulf Views! 3 Bedroom, 3 Bath in Holmes Beach, FL Blue Haven...

Sea Mist

Sea Mist

Sea Mist 3 Bedroom  |  Sleeps 6  |  3-7 Nights Overview Elevated 3 Bed, 2 Bath in Anna Maria, Florida just STEPS to Pine Avenue & Anna Maria City Pier 3 Bedroom, 2 Bath in Anna Maria, FL 1700 sq. feet  Highlights Kitchen, Dining Area, Living w/ TV 1 King...

Sol Mate

Sol Mate

Sol Mate 3 Bedroom  |  3-7 Nights | Sleeps 8Overview Beautifully updated, fresh, and clean elevated home which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue 3 Bedroom, 2 1/2 Bath in Anna Maria, FL...

Condo/Apartment Style Homes

Sunset Margarita

Sunset Margarita

Sunset Margarita 2 Bedroom  |  Sleeps 6Overview Luxury Condominium with Screened Lanai, Shared Heated Pool in One Particular Harbour 2 Bedroom, 2 Bath in Bradenton, FL 391 Aruba Circle #301 Less than 2 miles from the Anna Maria Public Beach in the highly desirable...

Sunset Dreams

Sunset Dreams

Sunset Dreams 2 Bedroom  |  Sleeps 4Overview Second Floor Condominium with Shared Heated Pool at Key West North 2 Bedroom, 2 Bath on Bradenton Beach, FL 1205 Gulf Drive North Located directly across the street from the gulf and beach with stunning views and not far...

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