
Holiday rentals with a pool in Shelter Island
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Top-rated rentals with a pool in Shelter Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

1 bedroom, 1 bath /Hillcrest/San Diego Zoo/Balboa
One bedroom, one bath with a pool in the Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area. Full kitchen, queen bed, queen sleeper sofa & crib. Indoor/outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Walking to restaurants/bars/shops/stores (Trader Joe's, Ralph's & Whole Foods). Walking to the Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only a $95/stay flat fee. High chair, Pack & Play Crib, crib mattress & cover are provided

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit
VERY PRIVATE, COMPLETELY RENOVATED 4BR 3 Bath mid-century home with heated saltwater pool, hot tub and fire pit in totally private backyard retreat. Redone top-to-bottom, inside/out with everything new. The beds are top of the line with very high quality 100% cotton sheets and bath towels. Conveniently we are centrally located in a safe, friendly neighborhood with beautiful mountain views in the back. We never charge any fees - as we want to provide the experience we hope to get when traveling.

ModernCoastal I View I Pool ITub
Spectacular canyon views are the backdrop to this stunning, modern newly renovated San Diego home! The jetted hot tub with water falling in the sparkling pool, the natural light streaming through the french doors, huge screened folding door, and skylights, the beautiful Great Room with the inviting living room, gourmet kitchen, indoor/outdoor dining, comfy beds, spectacular rooms & bath, sunset vista point, outdoor BBQ & backyard loungers and daybed are all designed to get you in vacation mode!

San Diego Villa with pool, spa & sunset views - S6
Escape to a private 5000SF paradise in the center of it all: experience Casa Blanca-a breathtaking, award-winning Spanish Villa settled peacefully in the heart of San Diego. Literally, four miles or less and you’ll be anywhere in SD! Relax to music by the pool/jacuzzi, enjoy time with family&friends gathered around your huge entertaining kitchen and open concept lounge floor,and enjoy spectacular sunset meals from any of your five balconies. Casa Blanca, imagination is your only limit.Join us!

The Endless Summer Condo!
Let your worries drift away at this 6th floor corner condo with panoramic ocean views! With floor to ceiling windows throughout, you'll feel like you're floating above the sea! Leave your toes in the sand or walk to PB's best restaurants and attractions in minutes! When you're done exploring, put on a Beach Boys record while having dinner with the family amid a golden sunset..ah the good life! Create cherished memories that will linger long after the sun sets, here, at The Endless Summer Condo!

Designer Luxury Rental With Pool
Welcome to Wander Haven, a luxury central rental. With it’s on trend design, custom built stock tank pool, array of amenities and thoughtful touches throughout, you won’t ever want to leave. But when do you do decide to venture out and explore all that beautiful San Diego has to offer, you will find the central location gets you to anywhere you want to be in minutes. You’re 15 minutes or less from beaches, downtown, balboa park, sea world, the zoo and hundreds of amazing bars and restaurants.

Modern Central SD Home w/ Pool & Spa Near Beach
Experience luxury at Bay Breeze Retreat, an exclusive oasis in the heart of Mission Bay, San Diego. This stunning residence features a private salt pool, outdoor jacuzzi spa, elegant fire pit, whole house water filter system and a state-of-the-art grill and kitchen. Inside, revel in contemporary upgrades which makes the place perfect for family gatherings of up to 8 guests. Walk to Luce Bar & Kitchen and Bird Rock Coffee. Minutes from downtown and top attractions, your perfect escape awaits.

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Lionhead - Private Boutique Home
Unwind in your private backyard resort, featuring a heated pool, complimentary Jacuzzi, cabana, and BBQ—perfect for watching planes soar over the city skyline. Amenities: High-speed Wi-Fi, Smart TVs, and a vintage record player. Location: Minutes from Downtown, the Convention Center, and easy highway access. 🏊🏼♀️🛟Optional pool heat is available for $50/day (stays under 5 days). To ensure the best experience, heating is applied to the full duration of your stay only.

OB studio, ocean views, hot tub & garage parking!
Casita De 7 Palmeras is an open floor plan studio located in Ocean Beach which is a central location to explore San Diego's best beaches and attractions. Spend the day at the beach, zoo, Sea World, or wherever, and then come back and unwind in the amazing hot tub or on the view terrace to enjoy the amazing sunset! Garage parking, top quality Cal King bed, ocean / bay views, fast & reliable WIFI, premium Direct TV HD channel package, and Fujitsu split air-conditioning!

UTC Venetian 3 miles La Jolla Beach UCSD Scripps
Approx 3 miles from the most famous La Jolla beach! Only a mile away from UCSD with bus stop right outside the side gate. One of the nicest and most convenient locations in UTC/La jolla. Located right by the 5 and 805 freeway w/52 nearby! Walking distance to Wholefoods, Chase & Citi bank, CVS, Rubios, Nordstroms Rack, Starbucks, CPK, Trader Joes, Ralphs, Wells Fargo, Ross, Best Buy, AMC movie theater, and many restaurants ALSO Westfield Shopping Mall and so much more!

Luxury Family Home Near Dining, Shops + Zoo
Welcome to Casa Clandestino🎋 Located in North Park, this fully remodeled 1914 Craftsman offers the perfect blend of location, privacy, and style. Enjoy a stunning outdoor area with a new 30 ft. Trex deck, heated pool/hot tub, resort furniture, 65-inch outdoor TV, market lights, and a 6-burner gas grill. Inside, find 4 beds, 2.5 baths, a chef’s kitchen, Carrera marble bathrooms, original hardwood floors, and coffered ceilings.
Popular amenities for Shelter Island rentals with a pool
House rentals with a pool

Stunning 2BR/2BA| Plunge Pool, AC, Private

Traveler's Dream:Outdoor Bar, Cabana, Arcade, Pool

the Belvedere

The Queen House

Travelers Oasis w/ Private Pool + Hot Tub

Resort Style Living with Pool, Spa, and Bay Views!

Tropical Oasis: spa, solar heated pool, waterslide

Upscale Resort House /Views, Saltwater Pool/Spa !
Apartment rentals with a pool

Enchanted Ocean Sunsets

Ocean front condo heart of pacific beach

Windows to the Ocean

Luxury Oceanfront Condo with Unbelievable Views

Cozy home central to beaches & attractions

Bay View Condo in Pacific Beach

Newly Renovated Luxury Oceanfront Condo

Ocean-Bay-Sunset View Condo in Pacific Beach!
Other holiday rentals with a pool

Central Lux Pool Estate •Views•Fireworks•Sleeps 14

Modern Luxury: FREE Heated Pool & Ocean Views

4 Bedrooms | Pool | Views | Games | Gym |

North Park Craftsman Oasis with Pool

Resort Style Paradise | Pool, Spa, Renovated, AC

Pacific Teatro

Sunset Cliffs Beach Home

Beach house with pool & hot tub!
Destinations to explore
- San Diego Holiday rentals
- Los Angeles Holiday rentals
- Las Vegas Holiday rentals
- Palm Springs Holiday rentals
- Big Bear Lake Holiday rentals
- Tijuana Holiday rentals
- Joshua Tree Holiday rentals
- Long Beach Holiday rentals
- Santa Barbara Holiday rentals
- West Hollywood Holiday rentals
- Santa Monica Holiday rentals
- Big Bear Holiday rentals
- SeaWorld San Diego
- Coronado Beach
- LEGOLAND California
- Rosarito Beach
- University of California-San Diego
- San Diego Zoo
- Petco Park
- San Diego Convention Center E Ent
- San Diego Zoo Safari Park
- Pacific Beach
- Tijuana Beach
- Balboa Park
- San Diego State University
- Torrey Pines State Beach
- Ocean Front Walk
- Mission Beach
- Oceanside City Beach
- Las Olas Resort & Spa
- Moonlight State Beach
- La Misión Beach
- Belmont Park
- Sesame Place San Diego
- South Mission Beach, San Diego
- San Onofre Beach





