Beach rentals in Siesta Key and Villas - Holiday Lettings - Holiday Rentals Siesta Key

Close

View larger map

Also consider

North America Holidays
173078 properties
United States Holidays
129776 properties
Florida Holidays
37153 properties

Siesta Key

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,222 Holiday homes

(2) Excellent 

Certificate of Excellence

26

Holiday villa in Siesta Key

Florida / Siesta Key

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £160 / night

£820 - £1,520 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from £160 / night

(19) Excellent 

28

Siesta Key holiday condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Swimming pool
“Awesome place! Comforts of home, but with an amazing view!!!” Loved our stay. Very comfortable beach getaway. Everything we needed was here. Great sunsets, beach, and pool. Saw two manatee, lots of pelican, and one turtle. The lanai overlooking the be
…see more

from £257 / night

£1,799 / week

Book View

from £257 / night

(1) Excellent 

24

Home rental in Siesta Key with swimming pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

from £137 / night

£958 / week

Book View

Responds fast!
avg. 2 hours 50 minutes

from £137 / night

30

Holiday condo in Siesta Key

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £122 / night

£568 - £851 / week

Book View

from £122 / night

(1) Excellent 

18

Holiday condo in Siesta Key

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £76 / night

£532 / week

Book View

from £76 / night

(1) Excellent 

38

Holiday townhouse in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £167 / night

£1,064 - £1,419 / week

Book View

from £167 / night

35

Holiday home rental

Florida / Siesta Key

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £254 / night

£1,773 - £2,731 / week

Book View

Responds fast!
avg. 1 hour 44 minutes

from £254 / night

(1) Excellent 

12

Apartment rental in Siesta Key

Florida / Siesta Key

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £92 / night

£639 / week

Book View

Responds fast!
avg. 3 hours 3 minutes

from £92 / night

(11) Excellent 

28

Holiday townhouse in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £141 / night

£983 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from £141 / night

30

Siesta Key holiday apartment rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £125 / night

£596 - £1,064 / week

Book View

Responds fast!
avg. 3 minutes

from £125 / night

16

Siesta Key holiday apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £151 / night

£1,061 - £1,511 / week

Enquire View

from £151 / night

19

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £89 / night

£621 - £1,199 / week

Enquire View

from £89 / night

14

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £168 / night

£1,174 - £1,698 / week

Enquire View

from £168 / night

14

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £86 / night

£600 - £1,050 / week

Enquire View

from £86 / night

30

Holiday apartment in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £81 / night

£546 - £1,142 / week

Book View

Responds fast!
avg. 3 minutes

from £81 / night

(13) Excellent 

21

Siesta Key holiday apartment rental

Florida / Siesta Key

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £142 / night

£940 - £1,490 / week

Book View

Responds fast!
avg. 59 minutes

from £142 / night

14

Holiday apartment rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £89 / night

£621 - £1,199 / week

Enquire View

from £89 / night

(2) Very Good 

13

Holiday apartment in Siesta Key

Florida / Siesta Key

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £92 / night

£639 / week

Book View

Responds fast!
avg. 3 hours 3 minutes

from £92 / night

36

Holiday apartment in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £156 / night

£1,093 - £1,773 / week

Enquire View

from £156 / night

(17) Excellent 

Certificate of Excellence

30

Holiday apartment rental

Florida / Siesta Key

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

Certificate of Excellence

from £110 / night

£603 - £922 / week

Book View

Responds fast!
avg. 1 hour 16 minutes

from £110 / night

26

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £156 / night

£1,093 - £1,773 / week

Enquire View

from £156 / night

(3) Excellent 

12

Holiday apartment in Siesta Key

Florida / Siesta Key

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £178 / night

£1,246 / week

Book View

Responds fast!
avg. 2 hours 48 minutes

from £178 / night

(2) Very Good 

10

Home rental in Siesta Key

Florida / Siesta Key

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £121 / night

£1,064 / week

Book View

from £121 / night

32

Holiday hotel apartment in Siesta Key

Florida / Siesta Key

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

from £115 / night

£805 / week

Book View

from £115 / night

46

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £105 / night

£731 - £1,355 / week

Enquire View

from £105 / night

(9) Excellent 

Certificate of Excellence

27

Holiday villa in Siesta Key

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

Certificate of Excellence

from £284 / night

£1,951 - £3,546 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from £284 / night

(1) Excellent 

25

Holiday condo rental

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly

from £64 / night

£447 / week

Book View

from £64 / night

21

Siesta Key holiday condo rental

Florida / Siesta Key

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £126 / night

£1,008 - £1,223 / week

Book View

from £126 / night

33

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £127 / night

£887 - £1,476 / week

Enquire View

from £127 / night

39

Holiday apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £105 / night

£731 - £1,355 / week

Enquire View

from £105 / night

30

Siesta Key holiday apartment rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £86 / night

£600 - £1,050 / week

Enquire View

from £86 / night

(6) Very Good 

26

Siesta Key holiday villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £128 / night

£1,277 / week

Book View

Responds fast!
avg. 1 hour 40 minutes

from £128 / night

17

Siesta Key holiday apartment rental

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £167 / night

£1,171 - £2,093 / week

Enquire View

from £167 / night

17

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £105 / night

£731 - £1,355 / week

Enquire View

from £105 / night

23

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £167 / night

£1,171 - £2,093 / week

Enquire View

from £167 / night

20

Siesta Key holiday apartment rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £155 / night

£1,086 - £1,699 / week

Enquire View

from £155 / night

(1) Excellent 

35

Holiday villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £106 / night

£740 / week

Book View

Responds fast!
avg. 54 minutes

from £106 / night

26

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £156 / night

£1,093 - £1,773 / week

Enquire View

from £156 / night

(1) Excellent 

23

Holiday home in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £82 / night

£1,008 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from £82 / night

(23) Excellent 

16

Siesta Key holiday apartment rental

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £110 / night

£710 - £1,490 / week

Book View

Responds fast!
avg. 59 minutes

from £110 / night

Top Destination reviews

2/2 Ground Floor Condo with Patio on Intracoastal
Siesta Key Condo

Condo is beautifully situated on instracoastal shoreline on Siesta Key looking out to Sarasota on mainland. It takes approximately 10 min to walk on to the stunning beach looking out to Mexican Gulf. The condo itself was spotless and had all the amenities required to make our stay so enjoyable. The patio with table, chairs and hammock were a welcome bonus and allowed to appreciate the beautiful surroundings without having to leave the condo !!! Since the original booking, the owner has been easily contactable and responsive with any questions we had prior to our arrival. Great value for money and would not hesitate to rebook for future visits.see more
Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach
Mr

My wife and I enjoyed the most wonderful holiday in this excellent villa. It was very comfortable, had everything we needed and more, and is perfectly situated for the beaches and Siesta Key village is a short walk or bike ride away. The pool was a great bonus. All together, this was a great holiday.see more
Siesta Key - 2bdrm on the beach - amazing views!!
Oceanfront views right on the beach in the low key area of Turtle Beach

My family consists of my wife, 14 and 11 year olds, and me. This condo has a King master bedroom with a Gulf water view, and a bedroom with bunk beds. Both bedrooms have their own shower and bathroom. The condo is on the low-key more residential side of Siesta Key called Turtle Beach. It is still very near supplies, restaurants, pubs, markets, post office, grocery and lunch spots. It's just that Turtle Beach is more secluded and less "Animal House" than downtown Siesta Beach. If you want to relax, fish, lay on the beach, read a book on the patio at sunrise or sunset, and watch the sun set over the Gulf every night in your windows, then this is your place. There is a nice sized living room with couch, chairs, and flat screen TV. It has a full operational kitchen with full refrigerator and all kitchen gadgets and supplies. We made two very nice meals there, lots of breakfasts', and had friends over several times for cocktails and beach time. The condo has it's own numbered parking spot, and a marina slip for each unit with a boat ramp very nearby. You can fish for snook in the marina, or the beach is great too for fishing. The condo is near the stairs, elevator and laundry but that did not make it loud, just convenient. There is a freshwater shower and a walkway over the dune right by the condo. The common pool is small but clean and close if you want to go beach-pool-nap mode. We chartered Siesta Key Fishing Charters and caught almost 100 fish offshore, 10 huge keeper Red Grouper that we ate in the condo, froze and took home, gave away and traded for other cool stuff. We also really enjoyed eating at Big Water Seafood Market, they will clean and cook your fish, or sell you some, or feed you at their restaurant. Both of those companies can also be found highly rated on TripAdvisor. That's how I found all three....and I couldn't be happier. It was a great vacation at a chill place decorated "beachy style", on a relaxed beach near nice convenient stops, all the while having Siesta Village and Siesta Key Beach just down the road. Siesta Village is awesome and less crowded on weekdays. We had no problem parking even with the July 4th weekend and the offshore powerboat racing both that week. That being said this is a rental condo, and they are not perfect, because they are used and loved. I miss it. We will go back. And, the owners are super good at communicating, troubleshooting, returning security deposits, and all the other things we would hope work well after a great relaxing week. Be careful shopping, there are a lot of condos that say waterfront that aren't oceanfront. and lots of condos aren't really on the ocean although you are made to believe they are, but this one really is. Big Gulf of Mexico views in your face for a week. Big sunsets. Big sunburns. Big bellies full of super fresh fish. Big smiles from your family and friends. I say, book it and dare to be called Vacation Hero....see more
Beautiful & Modern Condo - Walk to Beach & Village
A hidden gem

Arrived 13th June 16 and stayed for an amazing 3 weeks. Minor problem re A/C sorted promptly by Nicole the owner next day after arrival and a mix of beers sent via courier by Nicole same day for minor inconvenience - very much appreciated. Stayed with my wife,daughter and family friend. Very well appointed Condo with all mod cons and finished to a high standard - just loved it!! Spoilt for choice re restaurants in the area and beach which is fabulous very convenient. Pool in the complex really good and well maintained. A real plus having your own washer and dryer in Condo. Will definitely return - big thank you to Nicole and Boris for making our stay simply magical see more