Vacation Rentals & Villas in Cypress Pointe

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1,629 Houses

(9) Very Good 

24

A home from home - luxurious, family-friendly home

Davenport / Cypress Pointe

Davenport villa

4 8 7 nights min

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

Price per night from

$110

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$110

Great rentals within 20 miles that match your search

Distance approx 19.19 km from Cypress Pointe

(27) Excellent 

27

BEACHFRONT BUNGALOW Mermaid-Seahorse *Htd POOL*Pet

Florida / Indian Shores

Indian Shores house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Mermaid Seahorse” A great vacation. There were 8 of us had plenty of room for us. We liked the quaintness of the bungalow. Everything was very clean. The place was decorated so uniquely just perfect. The view of the ocean and pool was awesome. The gra
…see more

Price per night from

$325

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$325

Distance approx 19.59 km from Cypress Pointe

(1) Excellent 

18

Fully Remodeled! Oceanfront 3 BR/2 Bath

Florida / Indian Shores

Indian Shores condo

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great property!” Great location, great pool and awesome access to the beach. We were 6 adults in 3 bedrooms. Could have used more bath towels( had 6). And beach towels(had 2). Loved that beach chairs were available for our use. Great sunset view from
…see more

Price per night from

$365

Price per night from

$365

Distance approx 5.39 km from Cypress Pointe

(9) Excellent 

38

Waterfront and Golf Island Home away from Home

Florida / Dunedin

Dunedin apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Car not necessary

Price per night from

$150

Price per night from

$150

Distance approx 8.2 km from Cypress Pointe

8

8th Hole Retreat-PERFECT FOR STUDENTS OR JUST TO RELAX! Only $30 per night!!

Florida / New Port Richey

New Port Richey condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$35

Price per night from

$35

Distance approx 11.77 km from Cypress Pointe

(15) Excellent 

Certificate of Excellence

31

Beautiful 2 bedroom condo,mins. drive to beach, pool

Clearwater / Clearwater Beach

Clearwater apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$85

Responds fast!
avg. 9 minutes

Price per night from

$85

Distance approx 12.69 km from Cypress Pointe

(2) Excellent 

24

Affordable Luxury Directly On The Gulf Of Mexico.

Florida / Clearwater

Clearwater apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool

Price per night from

$75

Responds fast!
avg. 37 minutes

Price per night from

$75

Distance approx 16.68 km from Cypress Pointe

17

Paradise on the Gulf of Mexico 1/1 6th floor condo

Florida / Hudson

Hudson condo

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$86

Price per night from

$86

Distance approx 17.17 km from Cypress Pointe

12

Indian Rocks Beach Apt A

Florida / Indian Rocks Beach

Indian Rocks Beach apartment

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$165

Price per night from

$165

Distance approx 12.9 km from Cypress Pointe

28

Beach More Worry Less

Florida / Northdale

Northdale b and b

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 46 mi
  • Swimming pool
  • Air conditioning

Price per night from

$49

Price per night from

$49

Distance approx 11.8 km from Cypress Pointe

(9) Excellent 

30

Luxury Condo near Clearwater Beach

Florida / Clearwater

Clearwater apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly
“CLEARWATER'S BEST KEPT SECRET” The pictures sold me on this condo. It is exactly as it shows. Very clean, smells good. Great locations, all stores close on the same road as condo. Close to the beach. Owner kept in close contact throughout our pre-book
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Price per night from

$85

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$85

Distance approx 17.85 km from Cypress Pointe

31

Only 90 Steps to the Beach - AQUA Condo

Florida / Indian Rocks Beach

Indian Rocks Beach apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$160

Price per night from

$160

Distance approx 6.37 km from Cypress Pointe

(16) Excellent 

10

Geodesic Dome

Florida / Holiday

Holiday apartment

1 5 4 nights min

  • 1 bedroom
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Ms” Me and my children stayed for 11 days and had the most wonderful vacation!! Thank you Sharon and Ralph...y'all are the best!! We will definitely be returning!!
…see more

Price per night from

$120

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$120

Distance approx 11.48 km from Cypress Pointe

(6) Very Good 

9

Carriage House studio apartment - 5 min to beach

Florida / Clearwater

Clearwater apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Air conditioning
“Cozy upstairs studio 10 minutes from downtown” This small unit is perfect for a single person. Comfortable bed. Full kitchen. Nicely decorated. Lots of hangars. Budget and Avis car rentals are a 10 minute walk away. Close to St. Cecilia Church and
…see more

Price per night from

$99

Price per night from

$99

Distance approx 14.57 km from Cypress Pointe

35

Nostalgic 2 Bed / 1 Sofa Bed House Sleeps 6

Florida / Largo

Largo house

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$79

Price per night from

$79

Distance approx 8.88 km from Cypress Pointe

(14) Very Good 

25

(2024) Cozy Villa in Sunny Clearwater, Florida

Florida / Clearwater

Clearwater villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child Friendly
“very comfortable” the villa was extremely clean and comfortable! A great place to rent with no inconvenience. Definitely a recommendation! Thank you!
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Price per night from

$96

Price per night from

$96

Distance approx 8.22 km from Cypress Pointe

(5) Very Good 

15

Relaxing Retreat

Florida / Clearwater

Clearwater villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$66

Price per night from

$66

Distance approx 10.58 km from Cypress Pointe

(56) Excellent 

17

Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach

Florida / Clearwater

Clearwater cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool
“A wonderful and Perfect Oasis in Clearwater Beach” Thanks so much to Teresa & Max for a fantastic week in Key Lime Sweet Cottage (which is a sister villa of Orange Blossom Cottage). We could not fault the Villa and landscaped gardens, pools in any way
…see more

Price per night from

$106

Responds fast!
avg. 1 hour 26 minutes

Price per night from

$106

Distance approx 18.33 km from Cypress Pointe

(4) Excellent 

34

Joyce's BEACHFRONT Suite #2 On the BEACH 2 bedroom 2 full baths

Florida / Indian Shores

Indian Shores apartment

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$189

Price per night from

$189

Distance approx 8.41 km from Cypress Pointe

14

NEW High End Keys Style - Private Resort - Huge Dock, Pool, Spa, Fire Pit + More

Florida / New Port Richey

New Port Richey house

2 6 7 nights min

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

Price per night from

$250

Price per night from

$250

Distance approx 11.67 km from Cypress Pointe

24

3BR Clearwater Beach - Walk to Beach/Dolphin Views

Florida / Clearwater

Clearwater apartment

3 6 7 nights min

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

Price per night from

$310

Responds fast!
avg. 10 minutes

Price per night from

$310

Distance approx 19.27 km from Cypress Pointe

22

Excellent Location on Intracoastal & Beach Across the Street

Florida / Indian Shores

Indian Shores condo

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$184

Price per night from

$184

Distance approx 16.12 km from Cypress Pointe

(51) Excellent 

28

Original Beachfront Cottage located Directly on the Beach

Florida / Indian Rocks Beach

Indian Rocks Beach house

5 18 min stay varies

  • 5 bedrooms
  • sleeps 18
  • min stay varies
  • Nearest beach 0 mi
  • Child Friendly
  • Car not necessary

Price per night from

$695

Responds fast!
avg. 20 minutes

Price per night from

$695

Distance approx 19.51 km from Cypress Pointe

22

Bayshore Yacht & Tennis club Great Views Sleeps 5 Beach right across the street!

Florida / Indian Shores

Indian Shores condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$100

Distance approx 19.07 km from Cypress Pointe

21

Contemporary condo in a 55+ community

Florida / Seminole

Seminole condo

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$60

Price per night from

$60

Distance approx 2.07 km from Cypress Pointe

(1) Very Good 

18

3 Bed Town House on the water

Florida / Tarpon Springs

Tarpon Springs house

3 6 min stay varies

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

Price per night from

$180

Price per night from

$180

Distance approx 16.88 km from Cypress Pointe

12

Newly Renovated 2 Bedroom Condo in Paradise Lakes Nudist Resort

Florida / Land O Lakes

Land O Lakes condo

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

Distance approx 16.97 km from Cypress Pointe

50

Reel Inn on Clark Home

Florida / Hudson

Hudson house

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$78

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$78

Distance approx 16.23 km from Cypress Pointe

24

20th Ave 416 Home

Florida / Indian Rocks Beach

Indian Rocks Beach house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$139

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$139

Distance approx 7.53 km from Cypress Pointe

26

NEW! Updated Downtown Dunedin Home - Walk to Cafes

Florida / Dunedin

Dunedin house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$135

Responds fast!
avg. 10 minutes

Price per night from

$135

Distance approx 10.14 km from Cypress Pointe

30

Sandy Shores Beach House

Florida / Clearwater

Clearwater house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$400

Responds fast!
avg. 34 minutes

Price per night from

$400

Distance approx 10.39 km from Cypress Pointe

12

Enjoy a cozy 'at home' feeling and still be in walking distance to everything

Florida / Clearwater

Clearwater condo

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$96

Price per night from

$96

Distance approx 6.97 km from Cypress Pointe

(17) Excellent 

27

Beautiful 4 Bd Pool Home!

Florida / New Port Richey

New Port Richey house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$143

Price per night from

$143

Distance approx 11.41 km from Cypress Pointe

38

New to Market! Stunning Waterfront Townhome With Private Rooftop Deck

Florida / Clearwater

Clearwater townhouse

3 6 30 nights min

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

Price per night from

$175

Price per night from

$175

Distance approx 9.96 km from Cypress Pointe

(9) Very Good 

35

Gardenia Beach Hideaway "Private pool & hot tub!"

Florida / Clearwater

Clearwater house

3 10 min stay varies

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

Price per night from

$189

Price per night from

$189

Distance approx 11.83 km from Cypress Pointe

19

Beautiful 2/1 Furnished Condo just minutes from Clearwater Beach 55+

Florida / Clearwater

Clearwater apartment

2 4 min stay varies

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

Price per night from

$57

Price per night from

$57

Distance approx 17.85 km from Cypress Pointe

16

Gulfview at Dunes Point. NEW LISTING BY BEACHHOUSEFL

Florida / Indian Rocks Beach

Indian Rocks Beach condo

2 6 3 nights min

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

Price per night from

$199

Price per night from

$199

Distance approx 10.61 km from Cypress Pointe

(5) Average 

22

Award winning boutique Hotel on Clearwater Bch.

Florida / Clearwater

Clearwater condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$119

Price per night from

$119