Holiday Homes in Casey Key

April 2025

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May 2025

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Featured Holiday Homes in Casey Key and around

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (227)
"Amazing 3 day get away. The best place to stay in Venice! "
Tropical Villas of Venice Beach

New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

9.8 out of 10, Exceptional, (6)
"We really enjoyed the seating areas over the water and boats just outside the door. Room was clean. Staff at check in always seemed annoyed with us, even for just dropping off keys. "
The price is €148
includes taxes & fees
24 Apr - 25 Apr
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.6 out of 10, Exceptional, (43)
"Beautiful place right on the beach in a great location. We enjoyed our stay very much"
The price is €1,144
includes taxes & fees
1 May - 2 May
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Close to Beach Access #7, Short Walk to the Village

9.8 out of 10, Exceptional, (45)
"The property was very clean and the check in process was incredibly easy. Just a couple minor issues like some wall outlets not working and the shower/bathtub not draining very well. They provided us with beach towels, beach chairs and umbrellas. Close to the beach, shops and dining. Would recommend for couples and families. "
The price is €474
includes taxes & fees
2 May - 3 May
Close to Beach Access #7, Short Walk to the Village

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (31)
"This sweet home has an amazing backyard oasis. The pool house is very cool also and a great place to do yoga or watch a movie. The location is great—a very walkable neighborhood and an easy walk to shops and dining. Would definitely recommend!"
Private Oasis in Sarasota Florida

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

9.2 out of 10, Wonderful, (13)
"Great location! Clean, easy to find and perfect amount of room. "
The price is €195
includes taxes & fees
4 May - 5 May
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (172)
"Great location. Beach couple blocks away-walkable which is a plus for us. During spring break traffic is heavy so we can walk to beach or historic downtown or to local restaurants.Rented e-bikes for a few days and explored."
Private pool House with Fountains & Beach Walkable

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

6.8 out of 10, (6)
"Property was clean, larger than expected and host was very accommodating and responsive. "
The price is €436
includes taxes & fees
14 May - 15 May
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.6 out of 10, Exceptional, (12)
"The house was lovely and was close to many amenities and several beaches. The neighborhood was very quiet. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining

Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

9.0 out of 10, Wonderful, (57)
"The pool was not very clean. No lights in the BBQ area and pool area. No gas for BBQ , we have to buy it. "
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable

10.0 out of 10, Exceptional, (71)
"My husband and 3 teenagers had the best time. The house is exactly as described. It’s a beautiful home, inside and out. It is fully stocked with everything you would need and was very clean!! The host was very accommodating and helpful. Beaches, shopping, restaurants and fishing are all a short drive away. "
Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable

FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

10.0 out of 10, Exceptional, (100)
"This house was perfect!! Beautiful inside and out with a short walk to the beach. We enjoyed fishing from the beach, the Sand Bar for lunch and local fish from the market. House was well stocked with supplies for the beach and host was terrific with excellent communication. We have been to the area several times and this was by far and away our best trip. Just an amazing house and we cannot recommend it enough!!!!"
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

2-bedroom Spacious townhome in Osprey

10.0 out of 10, Exceptional, (6)
"property was immaculate, Host was very helpful, an excellent shower, beds very comfortable, location quiet and secluded.will stay again when in Osprey."
2-bedroom Spacious townhome in Osprey

Family Fun House near Siesta Key

10.0 out of 10, Exceptional, (8)
"longtime friends went for a week of golf to Sarasota. We were fortunate to find this property as it gave everybody their own bedroom own bathroom plenty of space to relax. Also, after our long days of golf, the pool was refreshing cleaned twice a week."
Family Fun House near Siesta Key

Breezy coastal duplex with private beach access & deck- dog-friendly

9.0 out of 10, Wonderful, (8)
"We had a lovely time.. needs to be updated. Area rug was very dirty.. could use some small upgrades. Kitchen well equipped."
Breezy coastal duplex with private beach access & deck- dog-friendly

4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

9.8 out of 10, Exceptional, (104)
"Good location to be close to airport and short drive to beaches. There’s lots to do in the area! We were a little frustrated when we arrived the pool was low on water so the pump had not been running. Had to have pool people and electricians there and didn’t get fixed until our last day. Pool guys did not do anything to clean besides dump chemicals so my husband was cleaning it and filling it with a garden hose so our kids could at least float in it. "
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

9.6 out of 10, Exceptional, (10)
"We loved the house and the location was perfect! "
The price is €824
includes taxes & fees
22 May - 23 May
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

9.6 out of 10, Exceptional, (29)
"Clean and very close to village."
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

10.0 out of 10, Exceptional, (31)
"We were very happy with this place. "
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Casey Key

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (84)
"Stay right on the beach. Drag your beach chair right down to the shore. Walk out the back door right into the sand. Watch the sunset from your patio. Unit was clean and tidy. Remodeled. It was in good condition. Beach equipment was sparse and the chairs and mats need to be replaced. Owner did not respond to our concerns about this until after we checked out 4 days later. That was a little disappointing. Even with the junk beach furniture I would go back again. "
The price is €691
includes taxes & fees
27 Apr - 28 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Rare private beachfront estate on Gulf of Mexico.

9.8 out of 10, Exceptional, (20)
"It was an amazing place to unplug and enjoy the gifts of the Gulf"
Rare private beachfront estate on Gulf of Mexico.

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4637)
"This place was perfect! I will be back!"
The price is €159
includes taxes & fees
1 May - 2 May
Tropical Beach Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.