Vacation Rentals

87 properties available

TW#13 — Standard North Cottage 1 Bedroom | 1 Bathroom | Sleeps 2 Enjoy the simple pleasures of island living at TW#13, a comfortable Standard North Cottage offering a peaceful place to relax between beach days and island adventures. With a cozy layout, full kitchen, and easy access to the beach, this cottage makes it simple to slow down and enjoy

Tradewinds Unit #TW13

$1,638^.00 - $2,331^.00 / per week

Unit 135A – Ground-Floor Coastal Studio | Studio/1BA | Sleeps 2 Settle into island time at Unit 135A! This comfortable ground-floor studio combines convenience and relaxed coastal charm, making it a wonderful choice for couples or solo travelers looking for an easygoing Florida getaway. With a King bed, full kitchen, semi-private courtyard, and co

HOT 13

Tortuga Unit #135A

$1,449^.00 - $1,827^.00 / per week

1 baths

2 guests

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Unit 267A – 1-Bedroom | 1-Bath Deluxe Partial View Corner Condo | Sleeps 4 Welcome to one of Tortuga Inn\'s most desirable accommodations! Unit #267A is a sought-after corner one-bedroom, one-bath deluxe vacation condominium offering expanded living space, upgraded features, and beautiful views of Sarasota Bay. Its coveted corner location provides

Tortuga Unit #267A

$2,205^.00 - $2,583^.00 / per week

TW#12 — Standard North Cottage 1 Bedroom | 1 Bathroom | Sleeps 2 Relax into the easygoing island lifestyle at TW#12, a comfortable Standard North Cottage just steps from the Gulf of Mexico. Designed with simplicity and convenience in mind, this cozy cottage is an inviting home base for days spent enjoying the beach, exploring the island, and soak

Tradewinds Unit #TW12

$1,512^.00 - $2,205^.00 / per week

Unit 229 – Second Floor | 2BR/1BA | Sleeps 6 Welcome to your island getaway! Unit 229 is a cozy second-floor two-bedroom, one-bathroom vacation retreat offering a comfortable layout, peaceful garden views, and a relaxed coastal atmosphere. Perfect for families or small groups, this inviting unit provides a comfortable home base for enjoying the po

Tortuga Unit #229

$1,890^.00 - $2,268^.00 / per week

Unit 267 – 2-Bedroom | 2-Bath Deluxe Partial View Corner Condo | Sleeps 6 Welcome to one of Tortuga Inn\'s most desirable accommodations! Unit #267 is a sought-after corner two-bedroom, two-bath deluxe vacation condominium offering expanded living space, upgraded features, and beautiful views of Sarasota Bay. Its coveted corner location provides a

Tortuga Unit #267

$2,520^.00 - $2,898^.00 / per week

Unit 166 – 2-Bedroom | 2-Bath Deluxe Condo | Sleeps 6 Welcome to your island escape! Unit #166 is a spacious two-bedroom, two-bath deluxe vacation condominium offering expanded living space, upgraded features, and the comforts of home for a relaxing Anna Maria Island getaway. Thoughtfully designed for families and small groups, this inviting condo

Tortuga Unit #166

$2,362^.50 - $2,740^.50 / per week

Unit 220 – Second Floor | Deluxe Gulf View Studio/1BA | Sleeps 4 Wake up in paradise! Unit 220 is a charming Deluxe Gulf-view studio offering a comfortable and relaxing island escape. Located on the second floor and accessible by stairs only, this inviting retreat combines coastal-inspired décor with updated finishes to create a bright, polished i

HOT 11

Tortuga Unit #220

$1,638^.00 - $2,016^.00 / per week

Room #134B – Ground-Floor Island Hotel Room | Sleeps 2 Keep it simple. Keep it comfortable. Enjoy the island. Room #134B offers relaxed hotel-style accommodations in a convenient ground-floor location, making it an excellent choice for couples or solo travelers looking for an easy Anna Maria Island getaway. Just steps from the resort pool and a s

HOT 15

Tortuga Unit #134B

$1,260^.00 - $1,638^.00 / per week

1 baths

2 guests

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Unit 167 – 2-Bedroom | 2-Bath Deluxe Partial View Condo | Sleeps 6 Welcome to one of Tortuga Inn\'s most sought-after accommodations! Unit #167 is a spacious two-bedroom, two-bath deluxe vacation condominium offering expanded living space, upgraded features, and beautiful views of Sarasota Bay. Designed for guests who appreciate a little extra, th

Tortuga Unit #167

$2,520^.00 - $2,898^.00 / per week

TW#21 — Deluxe North Cottage | Sarasota Bay Water Views 1 Bedroom | 1 Bathroom | Sleeps 4 Wake up to beautiful Sarasota Bay water views at TW#21, a welcoming Deluxe North Cottage offering a peaceful island retreat with the beach just steps away. With comfortable accommodations, an inviting living space, and unobstructed views of the bay, this cot

Tradewinds Unit #TW21

$1,764^.00 - $2,457^.00 / per week

Unit 165A – 1-Bedroom | 1-Bath Deluxe Condo | Sleeps 4 Welcome to your island escape! Unit #165A is a comfortable one-bedroom, one-bath deluxe vacation condominium offering expanded living space, upgraded features, and the comforts of home for a relaxing Anna Maria Island getaway. Thoughtfully designed for couples, small families, and friends trav

Tortuga Unit #165A

$2,047^.50 - $2,425^.50 / per week

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