Updating...

More filters (1)

High chair
Wireless Internet
Air conditioning
Swimming pool

Private pool
Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Cot available
Sauna
Sea view
Safe
Dishwasher
Children's pool
Ceiling Fans
Cribs
Shared outdoor pool (heated)
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Table tennis
Clothes dryer
Games room
Swing set or jungle gym
Pool or snooker table
Fax machine
Video player
Boat available
Staffed property
Private fishing lake or river
Trampoline
Climbing frame
Bicycles available
Towels provided
Linen provided
Microwave
Freezer
Fridge
Housekeeping Included

See all

Less

Parking
Car not required
Children under 5
Smoking allowed

Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

See all

Less

Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
Tennis in town

Water sports
Horse riding
Fishing
Golf within 30mins drive
Waterfront

See all

Less

50 beach rentals

Sort by:

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 14 minutes

Match: High chair

All filters match

Price per night from

$315

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

Match: High chair

All filters match

Price per night from

$189

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

2 bedrooms
1 bathroom

sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

Match: High chair

All filters match

Price per night from

$310

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

Match: High chair

All filters match

Price per night from

$315

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: High chair

All filters match

Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 8

Match: High chair

All filters match

Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

Match: High chair

All filters match

Price per night from

$266

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

Match: High chair

All filters match

Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

Match: High chair

All filters match

Price per night from

$311

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

Match: High chair

All filters match

Price per night from

$311

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

Match: High chair

All filters match

Price per night from

$271

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

Match: High chair

All filters match

Price per night from

$266

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: High chair

All filters match

Price per night from

$303

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

Match: High chair

All filters match

Price per night from

$161

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

1 bedroom
1 bathroom

sleeps 6

Match: High chair

All filters match

Price per night from

$229

Great rentals within 20 miles that match your search

Castnetter Beach Resort 6

Holmes Beach apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: High chair

All filters match

Price per night from

$315

Cumberland Road Paradise

Venice apartment

1 bedroom
1 bathroom

sleeps 1

Match: High chair

All filters match

Price per night from

$103

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

Match: High chair

All filters match

Price per night from

$476