Single Family Homes

Choose from one of our gorgeous luxury single family homes, from 2 bedrooms to 7 bedrooms, each with their own private pool and in a unique location on the island

A Wave From It All

A Wave From It All

A Wave From It All 3 Bedroom  |  Sleeps 10 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 and has...

Seaswept Mermaid

Seaswept Mermaid

Seaswept Mermaid 4 Bedroom  |  Sleeps 11Overview NEWLY LUXURIOUSLY RENOVATED with Heated Pool, Spa, Bay & Canal Views on Canal with Dock 4 Bedroom, 4 Bath on Anna Maria, FL Seaswept Mermaid Anna Maria, FL 34216 Need more room? Can be rented in conjunction with the...

Point’s Hideaway

Point’s Hideaway

Point's Hideaway 3 Bedroom  |  Sleeps 8  |  7 Night Minimum 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...

Decked Out

Decked Out

Decked Out 2 Bedroom  |  Sleeps 4  |  Max Occupancy 6Overview   Newly Renovated Single Family Elevated Home with HUGE Sunny Private Heated Pool    2 Bedroom, 2 Bath in Anna Maria, FL 1200 sq. ft. Highlights   Layout   Kitchen w/ Island seating for 2, Dining...

Fins Up

Fins Up

Fins Up 2 Bedroom  |  Sleeps 6  |  7 Night Minimum Overview Newly Constructed Elevated Two-Story Home (Duplex) with Pool 2 Bedroom, 2 1/2 Bath on Holmes Beach, FL Can be rented in conjunction with Fishful Thinking 308 A 65th Street Holmes Beach, FL 34217 1250 sq. ft....

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...

Salty Pirate

Salty Pirate

Salty Pirate 4 Bedroom  |  Sleeps 11 Overview NEWLY LUXURIOUSLY RENOVATED with Heated Pool, Spa, Bay & Canal Views on Canal with Dock 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...

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...

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/...

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.​...

Beachy Villa Vista

Beachy Villa Vista

Beachy Villa Vista 5 Bedroom  |  Sleeps 10 | 7 Night Minimum Overview UNDER MANAGEMENT & RECENTLY UPDATED - New PHOTOS COMING SOON! Single Family Vacation Home with Heated Pool, Spa,  & Deck with GULF VIEWs JUST 3 HOUSES DOWN FROM BEACH 5 Bedroom, 4 1/2 Bath...

Breaking Waves

Breaking Waves

Breaking Waves 6 Bedroom  |  Sleeps 12 | 7 Night Minimum 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...

As Far as the Eye Can Sea

As Far as the Eye Can Sea

As Far as the Eye Can Sea 7 Bedroom  |  Sleeps 18  |  5-7 Night Minimum Overview Beautiful New Construction 3 Story Single Family Home with Pool, Waterslide & Grotto, Rooftop Deck Bradenton Beach, FL 7 Bedroom, 6 Full & 2 Half Baths 108 7th Street South...

The Tiki

The Tiki

The Tiki 4 - 9 Bedroom  |  Sleeps 8-18Overview ELITE LUXURIOUS GULF-FRONT VILLA WITH PRIVATE BEACH, POOL, SPA & TIKI BAR Centrally located on the island in the heart of Holmes Beach, FL This listing is for informational purposes only.  We are no longer taking new...

2 Bedroom Homes (Duplex or Condo)

Shared Pool 

Palm Tree Paradise A

Palm Tree Paradise A

Palm Tree Paradise A 2 Bedroom  |  Sleeps 6 Overview Cute and cozy ground floor unit with shared hot tub and only steps to beach 2 Bedroom, 1 Bath 104 48th Street - A Holmes Beach, FL 34217 (Tiki Estate Guest Suite) This listing is for informational purposes only.  We...

Bay Breezes at Bayside Bungalows

Bay Breezes at Bayside Bungalows

Bay Breezes at Bayside Bungalows 2 Bedroom  |  Sleeps 6 Overview ​Beautiful Bayfront Ground Floor unit with shared pool 2 Bedroom, 1 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We are no longer taking new...

Sunset Dreams

Sunset Dreams

Sunset Dreams 2 Bedroom  |  Sleeps 4 Overview Second Floor Condominium with Shared Heated Pool at Key West North 2 Bedroom, 2 Bath on Bradenton Beach, FL 1205 Gulf Drive North Bradenton Beach, FL 34217 1449 sq. ft. Highlights Layout  Kitchen, Dining, Living w/ TV...

Bayside Bungalows – 1 to 3 Bedroom Apartments

 

A bayside building nestled on the northern tip of the island and only one block from Pine Avenue, the heart of the City of Anna Maria. Steps to the bay, shops, eateries, the city pier, and trolley stop… you can not pick a more perfect location to spend your time on the island.

Choose from one of our five gorgeously renovated apartments in the building, from 1 bedroom to 3 bedrooms, all with their own private entrances as well as shared pool & laundry. 

Bayside Cutie at Bayside Bungalows

Bayside Cutie at Bayside Bungalows

Bayside Cutie at Bayside Bungalows 1 Bedroom  |  Sleeps 4 Overview Adorable newly renovated ground floor unit with shared pool 1 Bedroom, 1 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We are no longer taking...

Barefoot by the Bay at Bayside Bungalows

Barefoot by the Bay at Bayside Bungalows

Barefoot by the Bay at Bayside Bungalows 1 Bedroom  |  Sleeps 6 Overview 1 Bedroom, 2 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We are no longer taking new bookings on this home. Highlights Layout   ...

Bay Breezes at Bayside Bungalows

Bay Breezes at Bayside Bungalows

Bay Breezes at Bayside Bungalows 2 Bedroom  |  Sleeps 6 Overview ​Beautiful Bayfront Ground Floor unit with shared pool 2 Bedroom, 1 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We are no longer taking new...

Blissful Bay at Bayside Bungalows

Blissful Bay at Bayside Bungalows

Blissful Bay at Bayside Bungalows 3 Bedroom  |  Sleeps 9 Overview Newly renovated 2nd floor unit with shared pool in bayfront building 3 Bedroom, 2 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We are no longer...

Bay Vista at Bayside Bungalows

Bay Vista at Bayside Bungalows

Bay Vista at Bayside Bungalows 3 Bedroom 2 Bath  |  Anna Maria Overview Newly renovated BAYFRONT 2nd floor unit with PANORAMIC VIEWS and shared pool 3 Bedroom, 2 Bath Bayside Bungalows 201 S Bay Blvd Anna Maria, FL This listing is for informational purposes only.  We...

Palm Tree Paradise A & B – 2 & 3 Bedroom Apartments
(Tiki Guest Suites)

 
Located in a building nestled directly behind our beachfront home, The Tiki, and only steps to beach access. Centrally located on the island in the middle of Holmes Beach and only minutes to everything. Can be rented individually, together, or in conjunction with the main home.

Choose from one of our two gorgeously renovated & unique units, each with their own private entrance as well as shared hot tub & laundry. Both units are as close to the beach as you can be without paying to be directly on the beach!

Palm Tree Paradise B

Palm Tree Paradise B

Palm Tree Paradise B 3 Bedroom  |  Sleeps 6 Overview Newly renovated 2nd floor unit with shared hot tub and only steps to beach 3 Bedroom, 3 Bath 104 48th Street - B Holmes Beach, FL 34217 (Tiki Estate Guest Suite) This listing is for informational purposes only.  We...

Palm Tree Paradise A

Palm Tree Paradise A

Palm Tree Paradise A 2 Bedroom  |  Sleeps 6 Overview Cute and cozy ground floor unit with shared hot tub and only steps to beach 2 Bedroom, 1 Bath 104 48th Street - A Holmes Beach, FL 34217 (Tiki Estate Guest Suite) This listing is for informational purposes only.  We...

The Tiki

The Tiki

The Tiki 4 - 9 Bedroom  |  Sleeps 8-18Overview ELITE LUXURIOUS GULF-FRONT VILLA WITH PRIVATE BEACH, POOL, SPA & TIKI BAR Centrally located on the island in the heart of Holmes Beach, FL This listing is for informational purposes only.  We are no longer taking new...

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