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

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. feet Under new management. Available for renting starting...

419 Clark

419 Clark

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

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....

Breaking Waves

Breaking Waves

Breaking Waves 6 Bedroom  |  Sleeps 12 Overview Single Family Vacation Home with Heated Saltwater Pool, Spa, Rooftop Deck with GULF VIEWs and 1 Block to Beach 6 Bedroom, 6 1/2 Bath in Anna Maria, FLHighlights Layout       Open layout and spacious Kitchen, Dining...

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  |  7 Night Minimum Overview 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

785 Jacaranda 3 Bedroom  |  3-7 NightsOverview Elevated 3 Bed, 2 1/2 Bath with Pool/Spa within easy walking distance of Bean Point beaches 3 Bedroom, 2 1/2 Bath in Anna Maria, FL 1500 sq. feet Under new ownership & management. Currently undergoing renovations and...

A Wave From It All

A Wave From It All

A Wave From It All 3 Bedroom  |  4-7 night minimum Overview Gorgeous Luxury Home with Heated Pool, Outdoor Pavilion, Hammock, and 6-8 Min Walk to Beach! 3 Bedroom, 3 Bath in Anna Maria, FL A Wave From It All Anna Maria, FL 34216 This home is brand new to rental market...

Sunsets on Carissa

Sunsets on Carissa

Sunsets on Carissa 3 Bedroom  |  Sleeps 6  |  7 Night Minimum Overview Newly Constructed Elevated Single Family Three-Story Home with Pool & Water Views 3 Bedroom, 2 Bath on Holmes Beach, FL 5710 Carissa Street Holmes Beach, FL 34217 1950 sq. ft. Highlights...

Point’s Hideaway

Point’s Hideaway

Point's Hideaway 3 Bedroom  |  Sleeps 8 Overview Single Family Home with Private Heated Pool &Rooftop Deck w/stunning sunset Water Views 3 Bedroom, 3 Bath in Anna Maria, FL 2300 sq. ft. Highlights   Layout  Kitchen, Dining, Living w/ TV 1 King Bedroom w/ TV,...

Fins Up

Fins Up

Fins Up 2 Bedroom  |  Sleeps 6Overview Newly Constructed Two-Story Home with Private Heated Pool 2 Bedroom, 2 1/2 Bath on Anna Maria Island 308 A 65th Street Holmes Beach, FL 34217 1250 sq. ft. Highlights Layout  Kitchen, Dining, Living w/ Soaring Ceilings & Queen...

Condo/Apartment Style Homes

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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