Updating...
Match: Tennis in town
All filters matchPrice per night from
$195
Match: Tennis in town
All filters matchPrice per night from
$137
Great rentals within 20 miles that match your search
Match: Tennis in town
All filters matchPrice per night from
$302
Match: Tennis in town
All filters matchPrice per night from
$345
Match: Tennis in town
All filters matchPrice per night from
$1,003
Match: Tennis in town
All filters matchPrice per night from
$115
Match: Tennis in town
All filters matchPrice per night from
$190
Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*
Siesta Key condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Tennis in town
All filters matchPrice per night from
$286
Fabulous private south facing villa with great golf course views
Rotonda West villa
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Tennis in town
All filters matchPrice per night from
$207
Match: Tennis in town
All filters matchPrice per night from
$369
Match: Tennis in town
All filters matchPrice per night from
$230
Match: Tennis in town
All filters matchPrice per night from
$212
Match: Tennis in town
All filters matchPrice per night from
$183
Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!
Siesta Key condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Tennis in town
All filters matchPrice per night from
$338
Match: Tennis in town
All filters matchPrice per night from
$296
“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.
Match: Tennis in town
All filters matchPrice per night from
$604
Match: Tennis in town
All filters matchPrice per night from
$97
Port Charlotte 3 bedroom, 2 bathroom heated pool villa
Port Charlotte villa
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Tennis in town
All filters matchPrice per night from
$99
“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.
Match: Tennis in town
All filters matchPrice per night from
$104
Match: Tennis in town
All filters matchPrice per night from
$161
Grand accomdation on USA #1 Beach - Siesta Key Fl
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Match: Tennis in town
All filters matchPrice per night from
$206
Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.
Match: Tennis in town
All filters matchPrice per night from
$166
Vacation Home on Alligator Drive . Winter 2025 Special !
Venice house
- 3 bedrooms
- 2 bathrooms
- sleeps 5
Match: Tennis in town
All filters matchPrice per night from
$150
“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!
Match: Tennis in town
All filters matchPrice per night from
$274
“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.
Match: Tennis in town
All filters matchPrice per night from
$511
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Siesta Key apartment
- 4 bedrooms
- 4 bathrooms
- sleeps 10
“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.
Match: Tennis in town
All filters matchPrice per night from
$516
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: Tennis in town
All filters matchPrice per night from
$273
“Location location” Great house convincent , clean , close to everything
Match: Tennis in town
All filters matchPrice per night from
$122
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: Tennis in town
All filters matchPrice per night from
$190
Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 1 hour 1 minutes
Match: Tennis in town
All filters matchPrice per night from
$267
Luxury All Inclusive Fully Furnished House on the Gulf Coast in Venice Florida
Venice house
- 3 bedrooms
- 2 bathrooms
- sleeps 2
Responds fast! avg. 54 minutes
Match: Tennis in town
All filters matchPrice per night from
$268
Match: Tennis in town
All filters matchPrice per night from
$403
Match: Tennis in town
All filters matchPrice per night from
$202
Match: Tennis in town
All filters matchPrice per night from
$192
“Perfect family cottage in Lemon Bay” Such a great little house and surprisingly bigger than pictures reveal. Perfect for a family with kids. 3rd toilet tucked away in laundry shed for easy access from pool. Great location as well, close to beaches, parks and many restaurants within walking distance. Definitely will rent there again. House was fresh, clean and inviting.
Responds fast! avg. 3 hours 39 minutes
Match: Tennis in town
All filters matchPrice per night from
$104
Match: Tennis in town
All filters matchPrice per night from
$190
Beautiful Home Near Many Golf Courses in LWR/Sarasota, FL.
Lakewood Ranch apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Tennis in town
All filters matchPrice per night from
$100
Private Heated Pool Home. Walk or bike to Shamrock Park and close to the beaches
Venice house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Tennis in town
All filters matchPrice per night from
$265