Vacation Rentals From Anchor Down Vacation Rentals

The main clubhouse and golf course — home to Riverstrand's 27 holes of Arthur Hills-designed golf

From $145/night

Condo in North America

127 Babbling Brook Run

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $199/night

Home in North America

128 Sweet Tree

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $199/night

Condo in North America

24th St Beach House

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 6

From $145/night

Condo in North America

5400 Gulf Dr 55 +

Anchor Down Vacation Rentals

1 Bed

1 Full Bath

Sleeps 4

Your whole estate at a glance — two houses, pool and spa, a pickleball court, putting green, and 75 palms on one private acre.

From $999/night

Home in North America

75 Palms

Anchor Down Vacation Rentals

8 Beds

6 Full Baths

Sleeps 23

Soak in the heated pool after dark — underwater lighting turns every evening into a resort moment

From $225/night

Home in North America

A Wave From It All

Anchor Down Vacation Rentals

4 Beds

3 Full Baths

Sleeps 10

Slide into the screened lanai and let your whole afternoon disappear by the water.

From $225/night

Home in North America

Agave Sun

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 10

Step back and take it all in — your private deck, heated pool, and boat dock all in one aerial view. This is the whole package, and it's yours for the week.

From $275/night

Home in North America

Anna Maria Seascape

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

Fill up the hot tub, let the deck expand around you, and decide whether tonight ends poolside or right here.

From $595/night

Home in North America

Aqua Luxe Escape

Anchor Down Vacation Rentals

5 Beds

4 Full Baths

Sleeps 11

From $150/night

Home in North America

Azario Sunrise

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $225/night

Condo in North America

Base House on Pine Ave

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 4

Step onto the beachfront and you'll understand why guests keep coming back — the sand, the sky, and the water are all right there.

From $500/night

Home in North America

Bay Dreamin

Anchor Down Vacation Rentals

4 Beds

3 Full Baths

Sleeps 8

From $199/night

Home in North America

Bayside Hideaway

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

From $199/night

Home in North America

Bloom Lagoon

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

Sink into the pool or stretch out on a lounger — your screened Florida oasis is waiting the moment you arrive.

From $199/night

Home in North America

Blue Chill

Anchor Down Vacation Rentals

3 Beds

3 Full Baths

Sleeps 8

From $199/night

Home in North America

Blue Heron House

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

From $225/night

Home in North America

Blue Iguana

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 10

Step outside and your private heated pool is waiting — cool blue water, loungers, and total privacy in the screened enclosure.

From $200/night

Home in North America

Boho Bungalow

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

Claim your lounge chair, grab a cold drink, and let the heated resort pool do the rest — this is the upgrade you booked.

From $199/night

Condo in North America

Bungalow at Margaritaville

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 5

From $199/night

Home in North America

Cape Vista GetAway

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

Step outside the gate and you've got it all — pool, basketball, tennis, and pickleball waiting.

From $99/night

Condo in North America

Cappy Hour

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 6

From $250/night

Home in North America

Casa Palma

Anchor Down Vacation Rentals

4 Beds

3 Full Baths

Sleeps 8

From $285/night

Condo in North America

Castaway In Margaritaville

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 5

Claim your lounger, drop the drinks cooler, and let the Florida afternoon stretch out. The heated pool is all yours — no sharing, no resort crowds, just tropical landscaping and open sky.

From $199/night

Home in North America

Coastal Vibes

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 7

From $225/night

Home in North America

Coco Loco

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 8

Sink into vacation the moment you step out back — your screened heated pool is waiting, with patio loungers ready for a sun-soaked afternoon.

From $199/night

Home in North America

Coral Breeze

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 4

From $450/night

Home in North America

Cortez Cabana

Anchor Down Vacation Rentals

5 Beds

3 Full Baths

Sleeps 14

Welcome to Dolphin Cabin — your waterfront escape with a screened pool, private dock, kayaks, and everything the Gulf Coast of Florida has waiting for you.

From $225/night

Home in North America

Dolphin Cabin

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

Pull up a lounger, let the sun drop, and watch the pool light up as Florida goes golden — your vacation starts the second you step through the gate.

From $199/night

Home in North America

Driftwood Dreams

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 10

Your waterfront retreat from above — private dock, paver patio, screened lanai, and the canal right in your backyard waiting for you.

From $199/night

Home in North America

Garry's Landing

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

Soak up the sun right outside your back door — heated pool, hot tub, lounge chairs, and swaying palms all yours for the week.

From $495/night

Home in North America

Hammock Hideaway

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 7

Float in the shared heated pool while the hot tub waits — your whole backyard is right here, steps from the sand.

From $200/night

Home in North America

Hidden Treasure Unit A

Anchor Down Vacation Rentals

2 Beds

1 Full Bath

Sleeps 6

Shared pool runs the full length of the yard. Hammock's already up. Deck steps lead to the upper floor. All of this is yours the moment you check in.

From $200/night

Home in North America

Hidden Treasure Unit B

Anchor Down Vacation Rentals

2 Beds

1 Full Bath

Sleeps 6

Step onto your private lanai and take in unobstructed bay views — the perfect sunset seat every evening.

From $225/night

Condo in North America

Holmes Beach Retreat

Anchor Down Vacation Rentals

3 Beds

3 Full Baths

Sleeps 7

From $199/night

Home in North America

House of Palms

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 8

From $150/night

Home in North America

Jerry's Gem

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

Spot how the layout works from the air — an acre of space to enjoy and call your own during the stay

From $300/night

Home in North America

Lake O' Woods

Anchor Down Vacation Rentals

3 Beds

3 Full Baths

Sleeps 12

From $199/night

Home in North America

Mermaid Bay

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 10

From $275/night

Home in North America

Mermaid Sunrise

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $275/night

Home in North America

Mermaid Sunset

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $199/night

Home in North America

Mermaid Villa

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 10

Chip a few balls onto the putting green while the rest of the group floats — the backyard keeps every generation busy all day.

From $375/night

Home in North America

Montauks Point

Anchor Down Vacation Rentals

5 Beds

3 Full Baths

Sleeps 14

From $199/night

Home in North America

Nautical Escape

Anchor Down Vacation Rentals

4 Beds

2 Full Baths

Sleeps 9

Ease into the hot tub while the pool glows just past the umbrella — this fenced-in slice of Florida is yours, and the only company you'll have is palms swaying overhead.

From $900/night

Home in North America

Ocean Star

Anchor Down Vacation Rentals

7 Beds

7 Full Baths

Sleeps 17

Stay up late in the entertainment space when the mood calls for it — the room comes alive after dark and keeps the energy going well past beach bedtime.

From $225/night

Condo in North America

One Particular Penthouse

Anchor Down Vacation Rentals

3 Beds

3 Full Baths

Sleeps 6

Soak until your shoulders finally drop — the private hot tub fits two and sits tucked in a tropical corner that feels like it's yours alone.

From $150/night

Home in North America

Palma Sola Oasis

Anchor Down Vacation Rentals

3 Beds

2 Full Baths

Sleeps 6

From $1,700/night

Home in North America

Palms at Sarasota Bay Retreat

Anchor Down Vacation Rentals

6 Beds

7 Full Baths

Sleeps 17

From $199/night

Condo in North America

Penthouse Retreat

Anchor Down Vacation Rentals

2 Beds

2 Full Baths

Sleeps 5

Vacation Rentals by Anchor Down Vacation Rentals

Vacation Rentals from Anchor Down Vacation Rentals

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