Vacation Rentals with Pool in Grand Cayman

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Filtering by: Swimming pool

283 vacation rentals
9

Seven Mile Beach Resort & Club - Steps to the beach

Grand Cayman / George Town

George Town condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$300

Price per night from

$300

(15) Excellent 

61

SMB-Grand 32, renovated 2Bd/2Bath,

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$175

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$175

(13) Excellent 

32

Three Little Birds -2BR+ Villa, Private Beach

Grand Cayman / Rum Point

Rum Point house

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Gorgeous, peaceful- perfect island setting!” We rarely saw any other guests while staying at Three Little Birds. The place is well appointed, clean, comfortable, with a fully stocked kitchen; lovely sitting room overlooking the little beach. Swimming
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Price per night from

$310

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$310

(25) Excellent 

48

Beachfront Cayman Island Condo on 7 mile beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“A DREAM COME TRUE” We are the type of people who always look for affordable alternatives to the fancy hotels and the condo we rented from Anandi was just what we needed. Comfortably spacious and well stocked, No 329 Sunset Cove became our home from
…see more

Price per night from

$500

Price per night from

$500

(4) Very Good 

29

Cayman Islands Divers Paradise 1st Floor Oceanfront Condo

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$184

Responds fast!
avg. 54 minutes

Price per night from

$184

(1) Excellent 

41

Coconut Beach by Grand Cayman Villas and Condos

Grand Cayman / Rum Point

Rum Point house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$995

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$995

(7) Excellent 

28

Designer Villa, in Tranquil and Beautiful East End

Grand Cayman / East End

East End apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Beautiful, well maintained home-great owner!” We spent a perfect week at this vacation rental which was a 1st class experience all the way while having all the comforts of home and more. The house is immaculate, beautifully furnished and the grounds a
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Price per night from

$370

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$370

(11) Excellent 

42

'Sun Cloud' Oceanfront Villa in Rum Point!

Grand Cayman / Rum Point

Rum Point house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Perfect Sunrises & Sunsets” Our second trip to the island, however this property made it a remarkable stay. A perfect location, tranquil, close to a small store, 4 minutes drive to Rum point and Cayman Kai. The house is beautiful, a view from every
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Price per night from

$725

Responds fast!
avg. 10 minutes

Price per night from

$725

(33) Excellent 

Certificate of Excellence

27

2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2

Grand Cayman / Rum Point

Rum Point apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Perfect in every way!” Hubby and I just returned from our 2 week stay in the Moonlight Kai condo. We had no concerns at all after reading all the wonderful reviews. The condo is and has almost everything listed (I'll explain further in my review) and
…see more

Certificate of Excellence

Price per night from

$179

Price per night from

$179

48

Amazing beach villa, with free electric car to explore the island

Grand Cayman / West Bay

West Bay villa

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$450

Price per night from

$450

(27) Excellent 

21

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

Grand Cayman / North Side

North Side apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location
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Price per night from

$288

Responds fast!
avg. 3 hours 19 minutes

Price per night from

$288

(36) Excellent 

41

3 Bed Condo with Huge Patio on Seven Mile Beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Excellent Condo With Very Attentive Owner” This is an excellent condo with wonderful view and large terrace. Its spacious and well worth the climb of three stairs. The apartment was probably the best equipped rental we have EVER stayed in (and we have
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Price per night from

$347

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$347

(15) Excellent 

20

Laguna del Mar: Prime Seven Mile Beach location ground floor beachfront

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$675

Responds fast!
avg. 1 hour 24 minutes

Price per night from

$675

29

The Reef Resort: 2-BR Lockoff, Sleeps 6, Kitchen

Grand Cayman / East End

East End villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$325

Responds fast!
avg. 3 hours 13 minutes

Price per night from

$325

(4) Excellent 

Certificate of Excellence

19

2 BR condo on Seven Mile Beach with ocean views

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$350

Responds fast!
avg. 2 hours 37 minutes

Price per night from

$350

(8) Excellent 

Certificate of Excellence

39

Ocean Views Long Sunsets 25 steps to water Ground Floor, pool outside front door

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$283

Responds fast!
avg. 42 minutes

Price per night from

$283

26

Fishbones by Grand Cayman Villas and Condos

Grand Cayman / Gun Bay

Gun Bay house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$600

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$600

(25) Excellent 

Certificate of Excellence

37

Starboard Kai Beachfront Home Rum Point Cayman Kai

Grand Cayman / Rum Point

Rum Point house

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the
…see more

Certificate of Excellence

Price per night from

$320

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$320

(5) Very Good 

25

Two Rainbows by Grand Cayman Villas and Condos

Grand Cayman / Rum Point

Rum Point house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Two Rainbows is a peaceful, secluded and affordable villa perfec” Our stay at Two Rainbows was our fourth visit to Grand Cayman. Check-in was absolutely painless. We had great instructions and were able to walk right in a get settled in a matter of
…see more

Price per night from

$1,100

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$1,100

(13) Excellent 

17

Cayman Beachfront at 22 Villas Pappagallo

Grand Cayman / West Bay

West Bay apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$213

Price per night from

$213

16

Updated 2 bedroom Ocean-Front Condo on the beach!

Grand Cayman / West Bay

West Bay condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$475

Price per night from

$475

19

Beach or Pool

Grand Cayman / East End

East End villa

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$288

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$288

(30) Excellent 

48

Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt

Grand Cayman / North Side

North Side apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.15 mi
  • Swimming pool
“Tranquility” Traveled to Grand Cayman with a couple girlfriends and chose Kai Kotch based on reviews here and was not disappointed! We wanted a peaceful vacation and that's exactly what we got. Kai Kotch #17 was spacious and clean and we really enjoye
…see more

Price per night from

$273

Price per night from

$273

(2) Very Good 

30

Morritt's Tortuga Club: 1-BR, Sleeps 4, Full Kitchen

Grand Cayman / Gun Bay

Gun Bay villa

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$138

(3) Excellent 

15

Oceanview/Poolside Condo on Seven Mile Beach

Grand Cayman / George Town

George Town condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$199

Responds fast!
avg. 20 minutes

Price per night from

$199

(24) Very Good 

24

Christmas Palms by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Wedding Week Stay” In a rare occurrence these days, Christmas Palms actually exists as it is portrayed in both photos and video. Everything aspect of our rental was as we hoped for and expected and would have no reservation in staying there again. T
…see more

Price per night from

$700

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$700

(7) Excellent 

24

Morning Glory

Grand Cayman / Savannah

Savannah villa

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$975

Price per night from

$975

(11) Excellent 

13

Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6

Grand Cayman / North Side

North Side apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Perfect paradise” This was perfect for my family of 2 teenage girls, my wife and I. We wanted the hot Caribbean vacation without the resort. We dove and explored everyday. This condo had everything we needed, pool, right on the sea, internet, full kit
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Price per night from

$249

Price per night from

$249

34

Britannia Villas 724

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$375

Price per night from

$375

(5) Excellent 

28

Kai Conut by Grand Cayman Villas and Condos

Grand Cayman / Rum Point

Rum Point house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“picture postcard sand beach and beautiful blue waters with soft” Twelve persons arrived at the Kai Conut villa and it was ready for relaxed living.Weather was tropical rainy but did not keep us down. Used the time to tour the island and went to Turtl
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Price per night from

$850

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$850

(2) Excellent 

27

Ocean Pearl Beachfront Townhome Vacation Rental

Grand Cayman / North Side

North Side house

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$249

Price per night from

$249

51

Surfers Paradise Oceanfront on the "New Seven Mile Beach"...come and relax !

Grand Cayman / George Town

George Town guest house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child Friendly

Price per night from

$794

Price per night from

$794

(14) Excellent 

24

Heritage House by Grand Cayman Villas and Condos

Grand Cayman / Rum Point

Rum Point house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Air conditioning
“Wow! What a great time” We had the pleasure of staying at the Heritage House for a week at the end of april/beginning of May. The house is not centrally located to the the main part of the island, it is beautifully secluded on the North End of the is
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Price per night from

$710

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$710

27

Sea-Esta Beach Front Kaibo Condo

Grand Cayman / Rum Point

Rum Point apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$179

Price per night from

$179

(6) Very Good 

24

Coral Kai by Grand Cayman Villas and Condos

Grand Cayman / Rum Point

Rum Point house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Wonderful Spring Break for 2 families” Outside deck was perfect place to relax, great lounge furniture, plenty of space, perfect size pool for kids, large beach area, sea weed visible but not an issue its the ocean there's always going to be some, but
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Price per night from

$1,100

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$1,100

(44) Excellent 

12

Truly Oceanfront luxury in Grand Cayman

Grand Cayman / Old Man Bay

Old Man Bay apartment

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Beautiful location” Beautiful view of the ocean and great location right on the beach in a quiet area of cayman. Condo has lots of amenities and a nice-sized swimming pool. We had a great time!
…see more

Price per night from

$224

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$224

(3) Excellent 

37

Kai Time Island House, Cayman Kai/Rum Point

Grand Cayman / Rum Point

Rum Point house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$313

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$313

28

Coconut Bay #109

Grand Cayman / West Bay

West Bay apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$215

Price per night from

$215