
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
4.99 out of 5 average rating, 192 reviews
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!
4.86 out of 5 average rating, 147 reviews
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.
5.0 out of 5 average rating, 302 reviews
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!
5.0 out of 5 average rating, 143 reviews
Luxury Oceanfront Condo with Unbelievable Views
Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.
4.98 out of 5 average rating, 225 reviews
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.
4.92 out of 5 average rating, 131 reviews
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.
4.96 out of 5 average rating, 180 reviews
Windows to the Ocean
Located by the Ocean in Pacific Beach, few blocks from the Crystal Pier, this luxurious 2-bedroom condo is steps away from restaurants, cafes, bars, nightlife, shopping and of course, the beach! Floor-to-ceiling windows from every room are perfect for enjoying unobstructed views of the ocean, either while sipping a morning cup of coffee or staring at a stunning sunset. Whether you are looking to experience an active beach-front lifestyle or just have a relaxing break, you will find it here!
4.92 out of 5 average rating, 217 reviews
Casa De Colores
Need some color in you life? Come stay in our one of a kind home- groovy wall mural, bright decor, rainbow speckled floors. Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Our property also offers the ultimate in convenience: - Acclaimed restaurants and cafes are just minutes away - Close to the Airport, Zoo, Balboa Park, and Downtown - Close to many world-class beaches
4.96 out of 5 average rating, 135 reviews
Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit
The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.
4.94 out of 5 average rating, 198 reviews
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.
4.93 out of 5 average rating, 293 reviews
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!
4.93 out of 5 average rating, 710 reviewsPopular amenities for Shelter Island rentals with a pool
House rentals with a pool

Resort Style Living with Pool, Spa, and Bay Views!
4.97 out of 5 average rating, 317 reviews
The Queen House
4.89 out of 5 average rating, 223 reviews
San Diego Oasis- A Retro Retreat w/ King Size Bed!
4.92 out of 5 average rating, 102 reviews
Your Modern Lux Pool Resort in the Heart of SD
4.9 out of 5 average rating, 189 reviews
ModernCoastal I View I Pool ITub
4.98 out of 5 average rating, 116 reviews
Designer Luxury Rental With Pool
4.94 out of 5 average rating, 150 reviews
Heated Pool + Hot Tub | Games | 10 min to Beach
4.98 out of 5 average rating, 118 reviews
Central coastal home - Ocean views and pool
4.87 out of 5 average rating, 150 reviewsApartment rentals with a pool

Bay View Condo in Pacific Beach
4.97 out of 5 average rating, 143 reviews
Cozy home central to beaches & attractions
4.92 out of 5 average rating, 200 reviews
Beautifully remodeled 10th floor oceanfront condo
4.97 out of 5 average rating, 208 reviews
Enchanted Ocean Sunsets
4.91 out of 5 average rating, 203 reviews
Ocean front condo heart of pacific beach
4.87 out of 5 average rating, 219 reviews
Oceanfront Elegant Condo - Remarkable Amenities
4.94 out of 5 average rating, 553 reviews
SEA Forever OceanFront Pacific Beach View Paradise
4.89 out of 5 average rating, 118 reviews
Ocean-Bay-Sunset View Condo in Pacific Beach!
4.98 out of 5 average rating, 112 reviewsOther holiday rentals with a pool

Hillcrest canyon home casita with pool access
4.89 out of 5 average rating, 143 reviews
Luxury Living Near the Beach
4.96 out of 5 average rating, 69 reviews
Luxury Point Loma Retreat, Pool, Spa, Views
5.0 out of 5 average rating, 18 reviews
Breathtaking Ocean, Bay, City & Petco Park Views
4.97 out of 5 average rating, 99 reviews
Sunset Cliffs Beach Home
4.92 out of 5 average rating, 52 reviews
Modern 3 bed/ 3.5 bath Townhome in Little Italy
4.96 out of 5 average rating, 72 reviews
Beach house with pool & hot tub!
4.89 out of 5 average rating, 46 reviews
3,500SqFt•RooftopPatio•La Jolla Cove|Shores•6 Beds
4.85 out of 5 average rating, 55 reviewsDestinations to explore
- San Diego Holiday rentals
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- SeaWorld San Diego
- Coronado Beach
- Rosarito Beach
- LEGOLAND California
- University of California-San Diego
- Petco Park
- San Diego Zoo
- San Diego Convention Center E Ent
- San Diego Zoo Safari Park
- Pacific Beach
- San Diego State University
- Balboa Park
- Tijuana Beach
- Torrey Pines State Beach
- Mission Beach
- Las Olas Resort & Spa
- Ocean Front Walk
- Oceanside City Beach
- La Misión Beach
- Moonlight State Beach
- Belmont Park
- Sesame Place San Diego
- South Mission Beach, San Diego
- San Onofre Beach





